# Between Two COOs — Full Episode Index > Long-form index of every Between Two COOs episode and blog post. Includes summary, chapter topics with timestamps, and people/companies/tools mentioned, for AI agents that need source material to ground answers about COO roles, execution, scaling, operations, leadership, AI in operations, remote work, and more. Each episode also has a full transcript at its canonical URL. Hosted by Michael Koenig (https://linkedin.com/in/michael-koenig514) — veteran COO, founder of Helm (https://helmapp.ai/), consultant. Generated: 2026-06-10 Episodes: 60 Blog posts: 1 --- ## Greg Keller, JumpCloud CTO on AI Agent Identity & Security URL: https://betweentwocoos.com/ai-agents-need-logins-too-identity-security-and-the-future-of-ai-greg-keller-cto/ Published: 2026-03-05 ### Summary In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI. Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke as companies moved to SaaS, cloud infrastructure, and remote work. The discussion then turns to the next big shift: the rise of AI agents and synthetic identities inside organizations. ### Topics Covered - What a CTO actually does (1:30) - Identity Access Management explained simply (4:00) - Why the old IT model broke (8:00) - How JumpCloud approaches identity (12:00) - Where Okta fits in the ecosystem (16:00) - Why COOs should push AI adoption (20:00) - The rise of synthetic identities (24:00) - Bots may soon outnumber employees (28:00) - AI as a potential insider threat (32:00) - The API key governance problem (36:00) - Key Takeaway: identity is the control layer (40:00) ### Mentioned in This Episode - Greg Keller on LinkedIn - Okta: Discussed as the company that modernized browser based single sign on - Ping Identity: Cited as an earlier single sign on pioneer before Okta - Model Context Protocol: Explained as the front door connecting AI agents to infrastructure - Microsoft Active Directory: The legacy identity system JumpCloud was built to replace --- ## Seth Levine of Foundry Group on Capital Evolution & AI URL: https://betweentwocoos.com/seth-levine-of-foundry-group-on-capital-evolution-ai-and-the-future-of-company-l/ Published: 2026-01-28 ### Summary In this episode, Michael Koenig speaks with Seth Levine, Managing Director at Foundry Group and co-author of Capital Evolution, about how American capitalism is changing and what that shift means for the people running companies. Seth traces the book to a board dinner after the Dobbs decision, where a portfolio CEO asked whether he would accept a lower return for the company living its values, and explains why businesses are pulled into roles once held by government and media. Seth contrasts Milton Friedman's shareholder doctrine with the dynamic capitalism the book proposes, built on long term thinking, a limited but real role for government, broader employee ownership, and respect for the rule of law. He cites executive pay up roughly 900 percent since Friedman's 1970 essay while average worker pay rose 12 percent, urges quarter by quarter planning for 2026, and recounts the AdMeld board crisis that preceded its half billion dollar sale to Google. Get 90 Days of Fellow's incredible AI notetaker for free at fellow.ai/coo ### Topics Covered - Introduction and sponsor message (0:00) - The 30 second pitch for Capital Evolution (1:57) - The board dinner question that sparked the book (2:22) - Coinbase, Jamie Dimon, and values versus politics (5:38) - The Business Roundtable redefines corporate purpose (10:00) - Where Friedman style capitalism went wrong (11:09) - The four tenets of dynamic capitalism (16:09) - AI and the future of work (19:47) - New graduates and the entry level sugar high (24:22) - The instability CEOs are quietly worried about (30:39) - AI in every boardroom and 2026 planning (34:50) - AdMeld's working capital crisis and turnaround (40:30) - The vodka luge story from 2001 (44:24) - Where to find Seth and the book (46:30) ### Mentioned in This Episode - Seth Levine on LinkedIn - Capital Evolution: Seth's new book at the center of the conversation - Foundry Group: The venture firm where Seth is managing director - The New Builders: Seth's earlier book with co-author Elizabeth MacBride - Business Roundtable: Its 2019 statement redefining the purpose of a corporation - Friedman Doctrine: Friedman's 1970 shareholder primacy essay the book pushes against - Strong Floor, No Ceiling: A recent book Seth cites on opportunity and inequality - AdMeld: Foundry portfolio company in the crisis story, later acquired by Google --- ## Brad Feld on Emotional Operating Systems & Giving First URL: https://betweentwocoos.com/brad-feld-on-the-emotional-operating-system-of-great-leaders-and-giving-first/ Published: 2026-01-20 ### Summary In this episode, Michael Koenig speaks with Brad Feld, partner and co-founder at Foundry, about Give First, his book on the philosophy that has shaped how he invests and lives. Brad explains why giving first is not altruism, how it differs from the transactional nature of pay it forward, and why positive sum, long term relationships elevate entire systems, using tennis and the Federer, Nadal, and Djokovic rivalry as his example. Brad shares the mentorship method he learned in YEO forum groups, where Socratic questions and stories replace telling founders what they should do, recounts the FullContact board meeting where the CEO finally demanded the answer, and separates the jobs of mentor, coach, therapist, and advisor. He closes with the day Sphero's second floor collapsed during peak holiday sales and Len Fassler's 2001 advice: they can't kill you and they can't eat you. ### Topics Covered - Cold open and Brad Feld introduction (0:00) - The Techstars t-shirt and Yoda story (2:42) - Give First versus pay it forward (5:01) - Positive sum relationships and the tennis example (7:35) - Why Brad has written nine books (14:17) - Writing as a search for meaning (19:43) - Pattern recognition and mentorship done right (22:34) - The FullContact board meeting story (30:01) - Management power dynamics and self-defined goals (32:22) - Building emotional intelligence as a leader (35:48) - Mentor versus coach versus therapist versus advisor (39:21) - Trust in mentor and coaching relationships (46:15) - The Sphero building collapse story (47:32) - Len Fassler's advice from the internet bubble collapse (53:08) ### Mentioned in This Episode - Brad Feld on LinkedIn - Give First: Brad's new book on mentorship and giving - Foundry: Venture firm where Brad is partner and co-founder - Techstars: Accelerator Brad co-founded, origin of Give First - Sphero: Portfolio company whose second floor collapsed mid holiday season - FullContact: Company in Brad's board meeting story - Feld Thoughts: Brad's blog post quoted in the cold open - Entrepreneurs' Organization: YEO forum groups shaped Brad's mentorship approach --- ## Peter Dougherty, Spreedly President on AI, Fraud & Commerce URL: https://betweentwocoos.com/ai-fraud-and-the-next-era-of-commerce-with-peter-dougherty-president-of-spreedly/ Published: 2025-12-10 ### Summary We dissect how go-to-market organizations evolve from $20M to $100M ARR, the power of focus and role separation, and how to keep silos aligned around one customer story. Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop. We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch. ### Topics Covered - Introducing Peter Dougherty and Spreedly (1:20) - Quadrupling ARR growth with flat operating expenses (3:23) - Evaluating people and what motivates them (4:26) - One-way doors and existential problems (5:36) - Spreedly's brand head start and open payments (11:53) - Scaling go-to-market from 20 to 100 million (14:48) - Customer centricity and avoiding silos (18:10) - OKRs and the company operating system (20:28) - Mentor lessons and perception versus reality (21:59) - Profitable growth versus growth at all costs (26:42) - AI, agentic commerce, and Google's payments protocol (28:07) - Orchestration leverage beyond payments (35:06) - The Dodgeball acquisition and fraud orchestration (38:20) - A full night shift at a nightclub (41:41) ### Mentioned in This Episode - Peter Dougherty on LinkedIn - Spreedly: Peter's company, the open payments platform discussed throughout - Lightspeed Commerce: Where Peter spent 12 years before joining Spreedly - Dodgeball: Fraud orchestration company Spreedly recently acquired - Agent Payments Protocol (AP2): Google's new protocol for agent-led payments --- ## Harris Clarke, GuideCX COO on Building Trust & Systems URL: https://betweentwocoos.com/the-power-of-calm-guidecx-coo-harris-clarke-on-building-trust-and-systems-that-h/ Published: 2025-11-13 ### Summary This week on Between Two COO's, Michael sits down with Harris Clarke, COO at GuideCX, to talk about what steady leadership actually looks like inside fast-changing companies. Harris started his career in protocol and operations for the U.S. Department of State, where “process” wasn’t just a buzzword — it was survival. He shares how those lessons translate to running a modern SaaS organization and why purpose, process, and payoff are the anchors of any good meeting. ### Topics Covered - SVB cold open and two-part recording note (0:00) - State Department protocol and customer experience (2:00) - The three Ps and lessons from bureaucracy (6:00) - Promotion to COO, mentors, and executive coaching (11:00) - Goal setting levers and framework discipline (14:00) - From insurance to Domo to GuideCX (17:00) - Curiosity, battle testing, and repeating the vision (22:00) - The human side AI cannot replace (26:00) - AI coaching rubrics, Gemini gems, and NotebookLM (28:00) - OKRs, transparency, and annual strategy planning (35:00) - Realistic optimism and the weight of words (40:00) - Creating the client onboarding category (46:00) - AI superpowers inside the GuideCX product (50:00) - SVB collapse and being the steady hand (53:00) ### Mentioned in This Episode - Harris Clarke on LinkedIn - Office of the Chief of Protocol: State Department office where Harris learned experience design - Domo: Harris's first SaaS role on the post-sales side - Domino's Pizza Tracker: Peter Ord's founding analogy for implementation tracking - Gemini: Used with gems to grade calls against coaching rubrics - NotebookLM: Used for investor updates and cited trend analysis - Silicon Valley Bank: GuideCX's bank during the collapse Harris describes --- ## Anna Elwood, Cascade COO on Turning Chaos Into Clarity URL: https://betweentwocoos.com/the-coo-who-turns-chaos-into-clarity-anna-elwood-of-cascade/ Published: 2025-10-28 ### Summary From Zocdoc to Cascade, COO Anna Elwood breaks down the systems, rhythms, and AI tools that turn chaos into execution. In this episode of Between Two COO's, Michael sits down with Anna Elwood, COO of Cascade, the strategy-execution platform helping companies turn plans into results. Anna shares how she evolved from Broadway actor to operator, scaling companies like Zocdoc, Knotel, and Teachable before joining Cascade to build the muscle of strategy execution. ### Topics Covered - Sponsor read and Superstorm Sandy cold open (0:00) - Introducing Anna Elwood, COO of Cascade (2:00) - From Broadway acting to Zocdoc operations (5:00) - First focus at Cascade, fixing retention (10:00) - Working rhythms and the move to hybrid (11:00) - Meeting cadences, KPIs, and accountability (13:00) - Governance, red tape, and Cascade's platform (15:00) - Five pillars of strategic maturity (17:00) - Turning strategy into measurable execution (19:00) - Diagnosing strategy versus execution problems (22:00) - AI inside Cascade and daily operations (25:00) - OKRs, frameworks, and platform flexibility (28:00) - Who owns strategy in an organization (34:00) - Superstorm Sandy and rebuilding headquarters overnight (37:00) ### Mentioned in This Episode - Anna Elwood on LinkedIn - Cascade: Anna's company, a strategy led performance platform - Zocdoc: Where Anna spent nearly a decade in operations - Knotel: Workspace company where Anna ran operations across continents - Asana: Michael's example of platform flexibility creating complexity --- ## Lance Willett, Automattic CQO on Powering 45% of the Web URL: https://betweentwocoos.com/automattic-chief-quality-officer-lance-willett-on-what-it-takes-to-power-45-of-t/ Published: 2025-07-23 ### Summary In this episode, Michael Koenig speaks with Lance Willett, Chief Quality Officer at Automattic, about what it takes to maintain quality at the company behind WordPress and WooCommerce, software that powers 45 percent of the web. Lance breaks down quality as a feedback loop between craft and context, then walks through how Automattic standardizes tools, governs AI experimentation, and ships AI products like support bots and a site builder. Lance gets specific about the operations behind that scale: an audit spanning more than 2,000 GitHub repos, WooCommerce stores that run 45 to 50 plugins each, quality benchmarks built on the DX Core 4, and a 20 dollar threshold for AI experiments. He also revisits stabilizing Tumblr through heavy turnover, Matt Mullenweg's insistence that details matter, and the 250,000 dollar revenue split error that still shapes how he leads. ### Topics Covered - How Automattic’s open source culture evolved over 20 years - What a Chief Quality Officer actually does—and why it matters - Quality = Craft × Context, and how that feedback loop scales - Automattic’s AI strategy: support bots, contextual UI, and site generation - The importance of tools like Linear and Storybook in enforcing quality - How Automattic balances speed, risk, and governance with AI experimentation - Lessons from stabilizing Tumblr during its post-acquisition reboot - Prioritization and the dangers of unbounded optimism - Leadership takeaways from working closely with Matt Mullenweg ### Mentioned in This Episode - Lance Willett on LinkedIn - WooCommerce: Automattic's commerce platform and a core quality challenge - Tumblr: The acquisition Lance helped stabilize as CTO - Linear: Issue tracker with opinionated triage flows and SLAs - Storybook: Tool for automated testing of UI components - DX Core 4: Framework measuring efficiency, speed, quality, and impact --- ## Linda Tong, Webflow CEO on Running Ops with AI at Scale URL: https://betweentwocoos.com/linda-tong-webflow-ceo-on-the-new-web-ai-powered-ops-and-how-they-run-webflow/ Published: 2025-07-08 ### Summary In this episode, Michael Koenig speaks with Linda Tong, CEO at Webflow, about how AI is reshaping the web and how she runs a platform serving 300,000 customers. Linda explains why she still codes on nights and weekends, why websites may need separate versions for humans and AI agents, and what Answer Engine Optimization means for anyone who depends on search traffic. Linda describes the stack rank she keeps in her head, weighing effort against impact to decide what to say no to, and the innovation lab she built at AppDynamics, complete with cross-functional hackathon rules and extra points for non-obvious ideas. She also recounts the SVB collapse weekend, four sleepless days spent securing payroll, and shares the tools she reaches for, from a custom GPT to Claude and NotebookLM. ### Topics Covered - How AI is changing what Webflow builds — and how fast they build it (3:30–13:00) - Why Linda still codes on weekends — and what it teaches her about the future of AI (6:00) - What happens when websites are no longer built just for humans (14:00) - The rise of AEO (Answer Engine Optimization) and what it means for ops (17:00–21:00) - Favorite LLMs and workflows — from Claude Sonnet to custom GPTs (23:00–26:00) - How Linda builds a culture of innovation — and why bad ideas are worth celebrating (29:00) - Leading through operational ambiguity and defining what to say “no” to (49:00) - How product thinking helps Linda prioritize and run the business (54:00) - Creating an actual in-office “innovation lab” — and what worked (1:04:00) - Wild story: how her team navigated the SVB collapse weekend (1:08:00) ### Mentioned in This Episode - Linda Tong on LinkedIn - Webflow: Linda's company and the platform discussed throughout - AppDynamics: Linda's prior company where she built the innovation lab - Lovable: tool Michael used for his 48 hour OKR app - ChatGPT: Linda's custom GPT writing partner for memos and email - Claude: Linda's pick for coding with Claude Sonnet 4 - NotebookLM: Linda's favorite for digesting long reports into podcasts - BOND AI Trends Report: Mary Meeker's 340 page report Linda discussed --- ## Doug Hanna, Kustomer COO on Agentic AI & Modern Ops Teams URL: https://betweentwocoos.com/kustomer-coo-president-doug-hanna-on-building-agentic-ai-running-sales-and-struc/ Published: 2025-06-04 ### Summary In this episode, Michael Koenig speaks with Doug Hanna, President and COO at Kustomer, about building agentic AI for customer service and running a modern go-to-market organization. Doug returns to the show after scaling Grafana Labs from 75 to over 1,000 employees, and explains why he chose the AI application layer next. The conversation moves from agents that resolve tickets to how Doug structures sales, RevOps, and weekly forecasting. Doug traces Kustomer's path through Meta, entering the acquisition near 300 people, spinning out with 90, and rebuilding to about 200. He cites AI resolution rates averaging around 40 percent, with one customer reporting 80, describes a new account manager role dedicated to upselling AI products, walks through centralizing RevOps and running a weekly MEDDPICC forecast, and warns against generic playbook application. Operators redesigning teams around AI will find concrete models here. ### Topics Covered - Doug's move from Grafana Labs to Kustomer (1:54) - Meta spinout and rebuilding to fighting weight (4:28) - Defining agentic AI in customer service (7:43) - From deflection to actual problem resolution (10:06) - Monitoring AI quality and cost trade-offs (12:12) - The gradient of human and AI handoffs (15:44) - Lower friction support and agent-to-agent future (19:25) - Operations lessons from Zendesk to Kustomer (22:31) - AI inside Kustomer's own operations (26:26) - Sales segmentation and the account manager role (30:31) - Centralizing RevOps into one team (33:06) - Weekly forecast cadence and data discipline (35:06) - Avoiding generic playbook application (40:16) - The one thing Doug wishes AI did (43:21) ### Mentioned in This Episode - Doug Hanna on LinkedIn - Kustomer: Doug's company, an AI-driven customer service platform - Grafana Labs: Doug's prior company, scaled 75 to over 1,000 employees - Zendesk: Doug's earlier company, origin of the weekly operational review - Meta: Acquired Kustomer and later spun it out as K2 - Gong: Call summaries Doug reads daily across customer conversations - ChatGPT: Kustomer provides ChatGPT Pro to all employees - MEDDPICC: Sales qualification framework used in Kustomer's forecast meetings --- ## Brad Rosen, Sales Assembly President on RevOps & Growth URL: https://betweentwocoos.com/sales-assembly-president-brad-rosen-on-unlocking-growth-and-why-revops-is-critic/ Published: 2025-04-29 ### Summary In this episode, Michael Koenig speaks with Brad Rosen, President at Sales Assembly, about revenue operations and why RevOps is critical for sustainable growth. Brad traces his path from finance to running RevOps at G2, where he was employee number three, and lays out the analytical, strategic, and execution work that makes go-to-market teams more effective. Brad cites an Andreessen Horowitz benchmark of one RevOps hire per ten go-to-market employees, recommends an 80/20 split between strategic projects and firefighting, and explains how the end of the zero interest rate era pushed companies from growth at all costs to efficiency. He also recounts comp plan rollouts at G2 that taught him the spreadsheet is just a sheet, and the pair compare notes after Michael fields a sales call from an AI agent. RevOps aligns and optimizes sales, marketing, and customer success, ensuring efficient and sustainable growth. ### Topics Covered - (02:00) What is RevOps and how Brad transitioned into it from finance - (07:00) Common misconceptions and early mistakes in RevOps - (11:00) Building a robust RevOps foundation and data hygiene - (15:00) Creating alignment across sales, marketing, and customer success - (20:00) Key metrics and strategic decision-making in RevOps - (24:00) AI’s impact on RevOps and potential pitfalls - (30:00) Real-world experiences with AI-powered sales calls - (33:00) RevOps vs. SalesOps and defining terms clearly - (36:00) Advocating for RevOps budgets and demonstrating value - (40:00) Lessons learned about effective communication and internal alignment ### Mentioned in This Episode - Brad Rosen on LinkedIn - G2: Brad joined as employee three and ran RevOps - Andreessen Horowitz: Brad cites their RevOps headcount ratio benchmark --- ## Aydin Mirzaee, Fellow CEO on Pivoting Meetings to AI URL: https://betweentwocoos.com/the-bold-pivot-from-meetings-to-ai-with-aydin-mirzaee-ceo-of-fellow/ Published: 2025-04-15 ### Summary In this episode, Michael Koenig speaks with Aydin Mirzaee, CEO and founder of Fellow, about pivoting a company with product-market fit from meeting productivity software to an AI meeting assistant. Returning nearly a year after his first appearance, Aydin explains why he believes Fellow would have gone extinct without a complete transformation of its product, pricing, teams, and culture. Aydin details the mechanics: replacing the value Pace Quickly with Fast and Fearless, weekly town halls with an AI show and tell, and the internal line that for the new Fellow to be born, the old Fellow must die. He also covers enterprise redaction, Shopify as customer number one, DeepSeek's effect on model costs, and why smart leaders spend 30 minutes to 2 hours a day keeping up with AI. ### Topics Covered - (02:00) Fellow’s shift from productivity tool to AI assistant. - (07:00) Implementing large-scale organizational change. - (13:00) Managing change and internal communications. - (20:00) Moving toward an agentic, automated workflow future. - (23:00) Unexpected real-world AI uses at Fellow. - (29:00) Privacy, security, and enterprise-grade compliance. - (33:00) Selecting and utilizing LLMs and managing AI economics. - (36:00) How to build an AI-first company from scratch. - (40:00) Why existing companies struggle to adopt AI effectively. - (44:00) Practical advice on starting AI implementation in established companies. ### Mentioned in This Episode - Aydin Mirzaee on LinkedIn - Fellow: Aydin's AI meeting assistant company and the subject of the pivot - SurveyMonkey: Acquired Aydin's last company before he founded Fellow - Outset: YC company building AI interviewers, cited as survey disruption - Shopify: Fellow's first customer, forcing enterprise-grade security from the start - DeepSeek: Chinese model maker cited for driving AI costs down - Cursor: AI code editor all Fellow development teams use --- ## Flick Fisher on the EU AI Act & Its Impact on US Companies URL: https://betweentwocoos.com/ai-and-privacy-navigating-the-eus-new-ai-act-the-impact-on-us-companies-with-fli/ Published: 2025-04-01 ### Summary Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo AI and Privacy: Navigating the EU's New AI Act with Flick Fisher In this episode of Between Two COO's, host Michael Koenig welcomes back Flick Fisher, an expert on EU privacy law. They dive deep into the newly enacted EU Artificial Intelligence Act and its implications for businesses globally. They discuss compliance challenges, prohibited AI practices, and the potential geopolitical impact of AI regulation. For leaders and operators navigating AI in business, this episode provides crucial insights into managing AI technology within regulatory frameworks. ### Topics Covered - Welcoming back Flick Fisher for The Legal Opinion (1:01) - The leaked final draft of the EU AI Act (2:01) - A risk-based approach to regulating AI (5:08) - The Brussels effect and US companies (6:41) - High-risk categories and prohibited AI practices (9:28) - What the leak reveals about defining AI (11:23) - Two-tier rules for general purpose AI (13:37) - Providers, deployers, and open source exemptions (15:49) - Foundation model thresholds and provider obligations (18:45) - Innovation concerns for OpenAI and Anthropic (20:52) - Phased deadlines and 35 million euro fines (22:56) - GDPR pace comparisons and social media lessons (24:04) - Environmental rules and new oversight bodies (27:34) - Employer obligations and Flick's legal opinion (30:34) ### Mentioned in This Episode - Flick Fisher on LinkedIn - Fieldfisher: The guest's law firm advising on EU privacy law - EU AI Act: The leaked regulation at the center of the conversation - GDPR: Reference point for the Act's global reach and pace - OECD AI Principles: Source of the Act's definition of AI - NYC Local Law 144: US law requiring bias audits in recruitment --- ## Cut Your SaaS Costs: COO Justin Etkin on Smarter Procurement URL: https://betweentwocoos.com/cut-your-saas-costs-coo-justin-etkin-on-smarter-procurement/ Published: 2025-02-05 ### Summary In this episode, Michael Koenig speaks with Justin Etkin, COO at Tropic, about how procurement has evolved from a back office cost cutting function into a strategic advantage. Justin explains why companies start formalizing procurement around a couple hundred employees, usually after a catalytic event like an unwanted auto renewal, and lays out the three pillars of good practice: centralized visibility, process controls, and scalable impact. The conversation gets specific: negotiating an Atlassian renewal through resellers working on thin margins, why the 20 percent of vendors driving 80 percent of spend stays human negotiated while the long tail gets automated, and how Tropic uses LLMs to extract and normalize contract data into pricing benchmarks. For COOs, CFOs, and anyone who owns vendor contracts, it is a practical introduction to modern procurement. ### Topics Covered - Introduction and welcoming Justin Etkin of Tropic (0:00) - The evolution of procurement beyond cost cutting (2:00) - When companies should formalize the procurement function (4:09) - Visibility, controls, and impact as procurement pillars (7:36) - Democratizing pricing data for technology buyers (10:57) - Negotiating an Atlassian renewal through a reseller (12:59) - Common mistakes when standing up procurement (16:02) - Efficient growth and the platform consolidation push (19:18) - AI agents, automation, and the human element (23:09) - Extracting and normalizing contract data with LLMs (28:38) - AI sidekicks and sentiment analysis for buyers (30:54) - Why procurement budgets trail go to market teams (35:17) - Procurement orchestration across legal, finance, and security (37:45) - Justin's wildest COO story: painting office walls (40:50) ### Mentioned in This Episode - Justin Etkin on LinkedIn - Atlassian: renewal example for negotiating through value added resellers - Coupa: cited as an enterprise source to pay suite --- ## Evan Grossman, True Search MD on Landing a C-Suite Role URL: https://betweentwocoos.com/true-search-managing-director-evan-grossman-on-how-to-land-your-next-c-suite-rol/ Published: 2025-01-21 ### Summary In this episode, Michael Koenig speaks with Evan Grossman, Managing Director at True Search, about how executives land C-suite roles that never reach a job board. Grossman, who leads True's CEO and board practice, explains how networks, talent partners at venture and private equity firms, and executive recruiters fill most senior roles before a posting ever exists, and how candidates can stay top of mind. Grossman describes why the market is opening for candidates with non-traditional backgrounds, how True's Thrive platform, used by Google and Starbucks, pares down candidate lists, and a CEO search where a career investor got a working session with the board to compete for the seat. He also explains culture fit, blind references, board readiness, and why COOs should gain hands-on experience in both value creation and value capture before pursuing a CEO role. ### Topics Covered - Introducing Evan Grossman and True Search (1:00) - How unposted C-suite roles get filled (2:04) - Breaking in without a strong network (6:50) - The LinkedIn thought leadership trap (9:50) - AI in executive search and Thrive (11:59) - Openings for non-traditional candidates (15:36) - Evaluating culture fit and blind references (20:43) - Self-awareness and executive communication (23:12) - Stretch roles and betting on yourself (26:21) - The search process from first call to offer (30:27) - Interviewing around two or three core needs (32:55) - When executives are ready for board seats (36:00) - What COOs need to become CEOs (39:19) - Two small-world stories from CEO searches (41:22) ### Mentioned in This Episode - Evan Grossman on LinkedIn - True Search: Evan's executive search firm, sixth largest globally - Thrive TRM: Talent platform True built, used by Google and Starbucks - Who: The A Method for Hiring: Hiring book Michael used to structure interviews --- ## Jon Mark, Vestwell COO on Strategy at Multi-Billion Scale URL: https://betweentwocoos.com/vestwell-coo-jon-mark-on-applying-strategy-and-tactics-to-build-a-multi-billion/ Published: 2025-01-08 ### Summary In this episode, Michael Koenig speaks with Jon Mark, COO at Vestwell, about applying strategy and tactics to build a multi-billion-dollar workplace savings platform. Jon's path from VP of Strategy at Vestwell to COO is grounded in the same problem-solving discipline he learned at Bridgewater. The conversation covers Vestwell's expansion from 401(k)s into student debt paydown, 529 education savings, and the Gratifi acquisition from Morgan Stanley. Jon walks through the chassis approach for SMB-focused financial tools, how AI integration shapes user experience, OKRs as alignment tools, and the operational realities of running a regulated fintech with mission-driven decision making. ### Topics Covered - Vestwell's platform and expanding beyond 401(k)s (0:00) - The retirement crisis and state auto IRA programs (4:36) - AI strategy and the new savings chatbot (9:29) - North star focus and the chassis approach (13:56) - Operating in a heavily regulated industry (20:02) - Career jump from strategy SVP to COO (22:02) - Finding mentors who invest in your development (25:25) - Managing imposter syndrome by going deep (27:16) - Asking questions without micromanaging (29:27) - Tying every risk to money and time (32:41) - Strategy and tactics as bets (35:18) - SMB mission focus and the mid market question (37:46) - Acquisition deal thesis and funded accounts OKRs (40:40) - Three crises the night before an acquisition close (46:51) ### Mentioned in This Episode - Jon Mark on LinkedIn - Vestwell: Jon's company, workplace savings platform discussed throughout - Bridgewater Associates: Where Jon trained in decision making and mentorship - Larry Fink's 2024 Chairman's Letter: BlackRock CEO's warning on the retirement crisis --- ## Valentin Gruber, HomeToGo COO on M&A & Going Public URL: https://betweentwocoos.com/hometogo-coo-valentin-gruber-talks-m-a-strategic-planning-and-taking-the-multi-b/ Published: 2024-07-16 ### Summary In this episode of Between Two COO's, host Michael Koenig sits down with Valentin Gruber, COO of HomeToGo, to explore the inner workings of the vacation rental aggregator and its strategy. HomeToGo went public via a SPAC in 2021, reaching a valuation of $1.2 billion after raising $150 million in VC funding. Valentin shares insights into the company’s growth, its approach to balancing marketplace and software solutions, and the strategic importance of acquisitions. The discussion delves into leadership principles, decision-making frameworks, and how HomeToGo navigates market complexities while competing with giants like Airbnb. Valentin also provides an entertaining look at innovative cost-saving measures the company employed, highlighting the unique culture at HomeToGo. This episode is a must-listen for anyone interested in strategic growth, leadership, and the evolving landscape of the vacation rental market. ### Topics Covered - Introduction to Valentin Gruber and HomeToGo (0:00) - From meta search to full marketplace (1:55) - Company scale and transaction volumes (5:14) - Subsidiaries and the build or buy question (7:19) - Splitting marketplace and Pro segment reporting (10:20) - Why HomeToGo built supply side software (11:51) - Strategic planning, problem statements, and prioritization (15:34) - Self critique and learning from failed bets (19:32) - Flat management and competency owners (22:34) - Questioning experts without undermining trust (25:45) - Pre-reads, working docs, and silent meeting starts (28:59) - What a SPAC is and why HomeToGo used one (33:54) - Allocating SPAC cash and evaluating acquisitions (37:51) - Flea market IPO bell and brunch negotiation (42:03) ### Mentioned in This Episode - Valentin Gruber on LinkedIn - HomeToGo: The vacation rental marketplace Valentin leads as COO - Smoobu: HomeToGo subsidiary syncing host listings across booking platforms - SECRA Bookings: Acquired software provider for vacation rental agencies - Atraveo: HomeToGo brand offering fully managed rental distribution - No Rules Rules: Book handed to every HomeToGo management team member - Lakestar: Sponsor of the SPAC that took HomeToGo public --- ## Stacey Ryan, School of Rock COO on Crisis Leadership URL: https://betweentwocoos.com/school-of-rock-coo-stacey-ryan-on-navigating-crises-change-leadership-and-empowe/ Published: 2024-04-23 ### Summary Navigating Leadership and Innovation at School of Rock with Stacey Ryan In this episode of Between Two COO's, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock - a global music school franchise. Stacey debunks a common misconception about the business's origin, noting it predated and inspired the 2003 film. She discusses the operational challenges of managing a global franchise, particularly through the COVID-19 pandemic, and highlights the innovative pivot to remote lessons and live-streamed shows. Stacey also delves into her role in founding Frontwoman.org, aimed at empowering women in leadership roles across various industries. The discussion covers her career trajectory, the importance of mentorship, operational strategies for scaling, and the significant impact of maintaining a supportive and innovative culture for both students and franchisees. ### Topics Covered - Introduction to Stacey Ryan and School of Rock (0:00) - School of Rock predates the Jack Black movie (2:02) - Pandemic response across 19 countries (3:08) - Overnight pivot to remote lessons and livestreamed shows (6:48) - Belonging, core values, and the AllStars program (10:37) - Assessing operations through feedback and KPIs (13:53) - Whiteboarding reorgs through rapid growth (16:32) - Putting everything in a box for franchisees (19:56) - Location planning and company school acquisitions (22:20) - Master franchising for international expansion (23:28) - Talent assessment and trusting your gut (26:30) - Maybe they're right and lessons from Rob Price (30:10) - Founding Frontwoman.org to empower women leaders (32:26) - Rhythm over balance and panel takeaways (37:41) ### Mentioned in This Episode - Stacey Ryan on LinkedIn - School of Rock: the global music education franchise Stacey leads - FrontWomen.org: nonprofit Stacey founded to empower women in leadership - Lean In: Sheryl Sandberg book Stacey calls her favorite - Shure: its CEO joined a FrontWomen panel discussion - GetYourGuide: prior episode example of pandemic accelerating online habits - Forum Analytics: site selection analytics program used for location planning --- ## Aydin Mirzaee, Fellow CEO on Mastering AI Productivity URL: https://betweentwocoos.com/fellow-ceo-aydin-mirzaee-on-mastering-productivity-and-efficiency-with-ai/ Published: 2024-04-09 ### Summary In this episode, Michael Koenig speaks with Aydin Mirzaee, CEO at Fellow, about meeting efficiency, structured management processes, and practical AI adoption inside a company. Aydin traces Fellow's origin to his previous startup's acquisition by SurveyMonkey, where he encountered one on ones and quarterly business reviews for the first time, and makes the case that recurring meetings are company processes that deserve deliberate design. They get specific: Fellow benchmarks meeting load at 7.5 hours per week for individual contributors and 15 for managers, runs 50 minute town halls, and can auto cancel any meeting that lacks an agenda an hour before it starts. Aydin also explains why the odds of reaching a decision fall sharply past seven attendees, how weekly AI presentations and employee AI budgets spread adoption, and the pendulum of management pattern drawn from nearly 200 Supermanagers interviews. ### Topics Covered - Meeting overload and Shopify's canceled recurring meetings (0:00) - Fellow's origin and the SurveyMonkey acquisition (1:52) - One on ones and QBRs as structured processes (5:33) - Scaling meeting templates at Shopify and beyond (10:09) - Making meetings actionable with action items (16:38) - Weekly meeting hour norms and Meeting Guidelines (21:34) - Participants versus attendees and agenda enforcement (25:09) - Asynchronous and hybrid meetings for remote teams (31:39) - Separating brainstorming meetings from decision meetings (38:48) - AI hackathons, budgets, and weekly AI presentations (43:49) - Governing AI use and protecting confidential data (49:52) - Weekly 50 minute town halls and CEO emails (55:46) - Lessons from nearly 200 Supermanagers interviews (1:00:54) - ChatGPT voice mode as a daily thinking partner (1:07:29) ### Mentioned in This Episode - Aydin Mirzaee on LinkedIn - Fellow: Aydin's company and the subject of the episode - SurveyMonkey: Acquired Aydin's previous company and taught him structured management - Shopify: Longtime Fellow customer that canceled all recurring meetings - Krisp: Tool Michael uses for noise removal and talk time stats - Oyster: Tony Jamous's company, source of the async video update example - Trust Me, I'm Lying: Ryan Holiday book Aydin uses for ChatGPT coaching sessions - ChatGPT: Discussed for data analysis and voice mode coaching --- ## Cameron Herold of COO Alliance on Second in Command URL: https://betweentwocoos.com/cameron-herold-of-coo-alliance-and-1-800-got-junk-on-how-to-delegate-lead-fix-pr/ Published: 2024-02-13 ### Summary In this episode, Michael Koenig speaks with Cameron Herold, founder of COO Alliance and former COO of 1-800-GOT-JUNK, about his new book The Second in Command. Back for a second appearance, Cameron takes a lightning round of questions on delegation, prioritization, feedback, promoting from within versus hiring externally, and how operators should approach AI. Cameron explains why your to-do list should not have your name at the top, sorts work into incompetent, competent, excellent, and unique ability buckets, and recalls Howard Behar handwriting thank you notes to Starbucks stores for two hours every Friday. He also revisits nearly bankrupting 1-800-GOT-JUNK at $60 million, when the CEO borrowed $420,000 from his mom to meet payroll, and closes with the Starbucks lesson on asking systemic rather than symptomatic questions. Presented by Fellow.app. Streamline your meetings and make them more efficient and meaningful. Get Fellow for you and your team today. Head to https://fellow.app/coo/ to get started and start having better meetings. ### Topics Covered - Cameron Herold returns with The Second in Command (0:00) - From second in command to the CEO seat (2:42) - Lessons from running a business at twenty (4:05) - Delegate everything except your unique ability (5:56) - Accountable people and business area review meetings (9:02) - Feedback culture where systems fail, not people (11:48) - Promoting from within versus hiring externally (15:31) - Bob and weave culture, not rigid plans (17:25) - Praise, gratitude, and Howard Behar's thank you notes (20:18) - Spending one to two hours weekly on AI (24:03) - Descript and Podium for podcast production (26:49) - Admired COOs at Facebook, Rippling, and GOT JUNK (29:23) - Near bankruptcy and learning to listen (32:13) - Ask systemic questions, not symptomatic ones (35:14) ### Mentioned in This Episode - Cameron Herold on LinkedIn - COO Alliance: Cameron's peer community for COOs and seconds in command - The Second in Command: Cameron's new book on the CEO and COO relationship - 1-800-GOT-JUNK: Where Cameron was COO, growing revenue to $106 million - Strategic Coach: Dan Sullivan's company behind the unique ability concept - There's An AI For That: AI tool directory Cameron's teams explore weekly - Descript: AI editing tool for podcast audio and video - Podium: AI show notes tool Michael uses for the podcast - Gerber Collision & Glass: Collision repair chain Cameron helped build through acquisitions --- ## EU vs AI: Flick Fisher on the Legal Opinion for US Companies URL: https://betweentwocoos.com/eu-vs-ai-what-you-need-to-know-about-the-eus-ai-act-the-legal-opinion-with-flick/ Published: 2024-01-30 ### Summary Could the EU's new AI Act be the cornerstone of global AI regulation? That's what we're here to unpack with the expert insight of Flick Fisher, a leading privacy specialist and partner at Fieldfisher. As the digital age accelerates, the European Union is setting a precedent with the AI Act, a groundbreaking legislation designed to navigate the complex terrain of artificial intelligence. Flick and I dissect the Act's risk-based approach, dissecting the prohibited and high-risk AI systems categories, while giving a nod to the lighter touch on low-risk innovations. Our conversation delves into how this monumental regulation could shape data privacy and ethical AI practices on the world stage. Join us as we explore not only the definitions and distinctions within the AI Act but also its everyday implications for business operations, from HR decisions to the product safety landscape. With generative AI technologies like ChatGPT on the rise, understanding the nuances of this legislative framework has never been more crucial. We'll navigate the potential new compliance roles the Act may create and predict whether this regulatory move could become the global gold standard. Tune in for a comprehensive analysis that will equip COOs and business leaders with the foresight needed to thrive in an AI-governed future. ### Topics Covered - Returning guest Flick Fisher and episode overview (1:01) - Refresher on what the EU AI Act regulates (2:08) - Prohibited AI practices from manipulation to social scoring (4:40) - How enforcement works and 35 million euro fines (7:46) - Keeping the law current as AI develops (10:01) - US launch strategies and the DeepSeek block in Italy (12:18) - The AI arms race and OpenAI's Italian fine (15:58) - US deregulation and Europe's regulatory response (19:25) - Governance advice for companies deploying AI (22:03) - HR bots and misinformation fears (24:44) - Common governance missteps and vendor diligence (27:22) - Government access fears and international data transfers (29:58) - Five year outlook and the Brussels effect (31:45) ### Mentioned in This Episode - Flick Fisher on LinkedIn - EU AI Act: the regulation at the center of the conversation - European AI Office: new EU body issuing guidance and enforcing the act - OpenAI: fined 15 million euros by the Italian regulator - DeepSeek: blocked in Italy over GDPR jurisdiction dispute - NIST AI Risk Management Framework: governance framework Flick cites as the gold standard - AI Opportunities Action Plan: UK government's principle based alternative to EU regulation --- ## Greg Strickland, Productboard COO on SMB to Enterprise URL: https://betweentwocoos.com/productboard-coo-greg-strickland-on-how-to-balance-growth-and-innovation-collect/ Published: 2024-01-24 ### Summary Join us as Greg Strickland, COO of Productboard, and I explore the power of embracing new opportunities and the crucial balance between business outcomes and personal advancement. Greg shares his journey of growth through accepting challenges that push boundaries, and we reflect on the times when a strategic 'no' can pave the way for others' development and align with company goals. Listen in for an insightful discussion on the mentorship gap in early-stage companies and the trial-and-error learning that COOs like Greg navigate in the startup landscape. As the startup ecosystem continues to evolve, we dissect the influence of continuous learning on company culture, inspired by industry pioneers. I open up about the enriching experience of partnering with product and engineering-driven founders and how passion plays a decisive role in a startup's trajectory. We consider how startups like Productboard are innovating in operations and product management with the use of AI, highlighting the agility required to manage rapid change and the ethical considerations of handling customer data. In our conversation, we delve into the challenges of scaling up to the enterprise market and the importance of building a culture that can gracefully manage internal friction points. I share my approach to fostering empathy and collaboration across departments, revealing personal anecdotes and strategies for aligning diverse perspectives within a company. Tune in for a rich discussion full of practical insights, memorable moments, and tips for nurturing a successful startup environment. Follow Productboard on LinkedIn and check out their blog for more engaging content that can help steer your company towards growth and innovation. ### Topics Covered - (00:06) Saying Yes to New Opportunities - (08:14) Startups' Impact on Learning Culture - (17:25) AI for Operations and Product Management - (31:34) Navigating Enterprise Market Challenges and Feedback - (37:07) Friction and Empathy in Customer Relations - (45:25) Developing Empathy and Cross-Departmental Collaboration ### Mentioned in This Episode - Greg Strickland on LinkedIn - Productboard: Greg's company, product management platform discussed throughout - Box: Greg's former company, recalled in the iPad market shift story - Salesforce: analogy for product ops becoming a system of record --- ## Tao of GetYourGuide on Building a $2B Travel Giant URL: https://betweentwocoos.com/get-your-guide-coo-tao-on-building-a-2-billion-dollar-travel-experience-giant/ Published: 2024-01-09 ### Summary In this episode, Michael Koenig speaks with Tao Tao, Co-Founder and COO at GetYourGuide, about building the Berlin based travel experiences marketplace into a $2 billion company. Tao traces the founding story from a dorm room at the Swiss Federal Institute of Technology, through a peer to peer tour guide platform that took four bookings in a year, to a marketplace that has sold over 80 million tickets across roughly 75,000 experiences. The conversation gets specific: revenue falling to a single booking during COVID, deciding against big layoffs while employees traded salary for stock options, and a $194 million Series F at a $2 billion valuation, split between $85 million in cash and a $109 million revolving credit facility with no liquidation preferences or warrants. Tao explains global network effects in travel, core values built by describing the people you would clone, and applying large language models to translation and customer service. ### Topics Covered - (00:11) The Travel Experience Industry Journey - (01:20 - 02:44) The Travel Experience Market's Growth - (04:36 - 06:03) Peer to Peer Tour Guide Platform - (07:27 - 09:26) Learning and Customer Obsession Importance - (12:35 - 13:56) Creativity and Execution in Strategy - (13:56) Adapting Culture and Surviving Crisis - (16:11 - 17:06) Identifying Core Values for Company Culture - (21:10) Travel Industry - (21:48 - 23:03) Accelerating Digitization and the QR Code - (31:53) Board Members, Funding, Global Network Effects - (36:32 - 37:43) Investment Strategy and Flywheel Approach - (39:48 - 40:47) International Tensions and Investment Impacts - (40:48) Travel and AGI Building Connections - (43:17 - 44:43) Applying AGI and AI to Operations ### Mentioned in This Episode - Tao Tao on LinkedIn - GetYourGuide: Tao's travel experiences marketplace, the subject of the episode - Booking.com: Its founder was an early board member and advisor - Delivering Happiness: Tony Hsieh book behind the first core values attempt - The Mind of the Strategist: Kenichi Ohmae book Tao cites on creativity in strategy - Vatican Museums: Turning on the lights private tour experience discussed - McLaren: Technology centre tour experience GetYourGuide created - Sagrada Familia: After hours private organ concert experience in Barcelona --- ## Allan Christensen, Doist COO on Remote Ops & Hiring URL: https://betweentwocoos.com/doist-coo-allan-christensen-on-remote-ops-perfecting-hiring-designing-ops-for-ca/ Published: 2023-12-19 ### Summary In this episode, Michael Koenig speaks with Allan Christensen, COO at Doist, about building a remote-first company without institutional investment. Doist, maker of Todoist and Twist, has been remote since 2007 with people in over 35 countries. Allan recounts his path from third-generation pipe organ builder to meeting Doist founder Amir Salihefendic at an expat soccer match in Chile, an exchange he only later realized was a job interview. Allan describes the hiring system Doist built from Laszlo Bock's Work Rules, scoring candidates one to four across at least three interviews and a test task, and notes that only four people left voluntarily in the company's first seven years. He also covers the head of remote role, six-month stable squads, a four-level flat hierarchy with career frameworks in Pando, and a Swiss trademark dispute in which a court ruled the registration fraudulent. ### Topics Covered - Introducing Doist COO Allan Christensen (0:00) - From pipe organs to tech (1:09) - Meeting Doist's founder at a soccer match in Chile (3:40) - Dividing responsibilities between COO and CEO (5:34) - What a head of remote does (7:34) - Why remote is its own function at Doist (10:24) - What asynchronous communication actually means (13:57) - When to work async versus sync (15:50) - Why most companies returned to the office (18:03) - A hiring process built on Work Rules (21:57) - Watching company culture form at annual retreats (25:38) - Career progression in a flat hierarchy (27:07) - Hands-on managers and stable squads (30:24) - A fraudulent Swiss trademark fight (33:14) ### Mentioned in This Episode - Allan Christensen on LinkedIn - Doist: Allan's company, maker of Todoist and Twist - Todoist: Doist's flagship task management app - Twist: Doist's asynchronous communication platform for remote teams - Pando: career progression platform Doist adopted for feedback and growth - Work Rules!: Laszlo Bock's book that inspired Doist's hiring process - Start-Up Chile: accelerator program where Allan met Doist's founder --- ## Dan Siroker of Rewind.ai & Optimizely on AI & Memory URL: https://betweentwocoos.com/rewind-ai-optimizely-ceo-founder-dan-siroker-on-augmenting-human-memory-with-ai/ Published: 2023-12-05 ### Summary In this episode, Michael Koenig speaks with Dan Siroker, co-founder and CEO of Rewind.ai, about augmenting human memory with AI. Siroker, who previously founded Optimizely and grew it to $120 million in ARR, explains how losing his hearing in his twenties inspired Rewind, a privacy-first tool that makes everything you see, say, or hear on your Mac searchable with AI. The conversation covers the pivot from Scribe, a cloud meeting bot, to a local-first Mac app made possible by Apple's M1 chips, and why Rewind's 18-person team moves faster than the 450-person Optimizely once did. Siroker also shares how Optimizely became the San Francisco Business Times number one best place to work, his two-by-two view of psychological safety, and the back-channel reference question he relies on when hiring. ### Topics Covered - (00:11) Augmenting Human Memory With AI - (05:11 - 05:38) Memory and the Evolving Digital Age - (06:56 - 08:05) Tech and Memory Retrieval - (11:40 - 12:51) Chat GPT and Data Privacy Integration - (12:51) The Future of AI in Operations - (17:34 - 18:44) Leveraging AI for Company Augmentation - (18:44) Enhancing Productivity With Artificial Intelligence - (22:34 - 23:47) AI for Efficiency and Exceptional Hiring - (27:19) The Impact of STEM on Technology - (30:31 - 31:01) Pivoting to Capture Meeting Data - (38:29) COOs and Chiefs of Staff - (38:38 - 39:00) COO and Chief of Staff Collaboration - (42:23) Cultural Values in a Company - (43:27 - 44:27) Using Cultural Values as a Guide - (45:58) Psychological Safety in Leadership Importance - (47:10 - 48:20) Accountability and Candor in Successful Teams - (52:03) Ask the Right Question and Succeed - (55:58 - 57:01) Impressions of AI Summarization ### Mentioned in This Episode - Dan Siroker on LinkedIn - Rewind: Dan's personalized AI memory tool, the episode's main subject - Optimizely: Dan's previous company, grown to 120 million in ARR - OpenAI: Rewind's GPT-4 integration and its training policies discussed - This Week in Startups: Jason Calacanis interview with Dan referenced on privacy --- ## Kate Henningsen, Arcadia COO on Clean Tech & Energy URL: https://betweentwocoos.com/arcadia-coo-kate-hennigsen-on-clean-tech-and-disrupting-the-energy-market-non-tr/ Published: 2023-11-21 ### Summary In this episode, Michael Koenig speaks with Kate Henningsen, Co-founder and COO at Arcadia, about clean tech and disrupting the regulated energy market. A former corporate litigator, Kate explains why energy is the only market still run as a regulated monopoly, and how legal and policy backgrounds became the founders' wedge into it. Topics range from community solar economics to Arc, Arcadia's B2B data platform serving EV manufacturers and solar developers. The conversation gets specific: more than 1.6 gigawatts of community solar under management, 300 million dollars raised, a recent 1.5 billion dollar valuation, five acquisitions in three years, and a global operations integration that cut cost to serve by 50 percent. Kate shares her counter deck for vetting acquisitions, five board meetings a year, the five cease and desist letters utilities sent in Arcadia's first 18 months, and the cold email that connected her with her co-founder. ### Topics Covered - (00:12) Clean Tech and Disrupting Energy Market - (06:15) Community Solar and Renewable Energy Innovation - (15:37) Data Platform and Energy Transformation - (24:21) Acquisitions, Integration, and Board Composition - (29:05) Startup Board Management and Risk Balancing - (35:51) Leadership, Growth Mindset, and Overcoming Challenges - (42:18) Connecting Through Cold Emails ### Mentioned in This Episode - Kate Henningsen on LinkedIn - How to Avoid a Climate Disaster: Bill Gates book Michael cites for emissions numbers - Rewiring America: Nonprofit quantifying the four billion machines to electrify --- ## Darren Murph, Fmr GitLab VP Remote on Remote Operations URL: https://betweentwocoos.com/perfecting-remote-work-operations-with-darren-murph-fmr-gitlab-vp-remote/ Published: 2023-10-17 ### Summary In this episode, Michael Koenig speaks with Darren Murph, VP of Workplace Design and Remote Experience at Andela, about the operations that make remote companies succeed. Murph, who previously led workplace strategy and operations at GitLab, scaling the world's first fully remote company to IPO, explains why low context communication is the foundation of remote operations and why companies must optimize for the speed of knowledge retrieval over the speed of knowledge transfer. Murph shares the no agenda, no attend rule from the Andela playbook, explains why remote work must be treated as an operating model rather than a perk, and argues that a documented knowledge base is now a prerequisite for generative AI. The conversation covers a Paychex finding that remote employees with poor onboarding are 115 percent more likely to quit in their first year, Dropbox's virtual first model, and carbon offsets for getting teams together. ### Topics Covered - Introducing Darren Murph and the remote operations focus (0:00) - Low context communication as the dark horse skill (2:32) - Optimizing for the speed of knowledge retrieval (6:45) - Remote as an operating model, not a perk (8:59) - Building remote operations without new headcount (12:27) - The no agenda, no attend meeting policy (17:08) - Measuring remote productivity and wasted hours (19:25) - Generative AI needs a documented knowledge base (21:58) - Remote onboarding and the Paychex retention study (24:31) - Creating personal connection on remote teams (27:52) - Luna Park and Dropbox's virtual first model (33:01) - Balancing team gatherings with carbon offsets (36:03) - Town halls and the teach, inspire, learn framework (41:18) - Darren's World Economic Forum story (43:46) ### Mentioned in This Episode - Darren Murph on LinkedIn - Andela: Murph's company and source of the no agenda policy - GitLab: Where Murph scaled the first all remote company to IPO - GitLab Handbook: Public handbook discussed as the company operating manual - Guru: Knowledge management tool hosting the Forrester ROI study - Luna Park: Comedian hosted virtual game shows for team engagement - Pachama: Carbon offset platform recommended for travel emissions - Dropbox: Cited as a model virtual first company - Tucows: Michael's company refining its remote operating practices --- ## Nitin Gupta, Prisma COO on Open Source & Hackathons URL: https://betweentwocoos.com/prisma-coo-nitin-gupta-explains-tech-to-my-mom-operationalizing-hackathons-the-b/ Published: 2023-09-26 ### Summary Unlock the secrets of remote team management and product explanation in our stimulating conversation with Nitin Gupta, the COO of Prisma. Nitin unveils how explaining technical products to non-technical people can be a challenge, but he makes it understandable, going as far as breaking down Prisma into simple terms for our mothers. Also, learn about Prisma University, a unique internal initiative to educate non-tech team members about their product's nuances. Beyond product explanation, we venture into the world of remote hackathons and the operational challenges within. Nitin highlights anticipating potential issues within a remote team and the significance of aligning all-hands meetings with the organization's structure. More so, we explore Prisma's unique take on transparency and collaboration as they open-source their processes. Finally, we delve into the less conventional aspects of managing a remote company. Nitin shares insights on why they hired a trained psychologist for HR and how it helps prevent employee burnout. He also unveils an interesting balance between commercializing open-source projects and maintaining a vibrant community through the 123 framework. Additionally, we discuss operational execution, aligning teams to KPIs, and Nitin’s unique approach to quarterly planning. This episode is a must-listen for tech enthusiasts and remote team managers looking for practical tips and fascinating insights. ### Topics Covered - Introducing Nitin Gupta and Prisma (0:00) - Explaining Prisma to mom in three layers (1:13) - Prisma University and hiring for curiosity (5:16) - Mentoring programs and internal hackathons (7:08) - Operationalizing a 72 hour remote hackathon (11:05) - All hands format and the SVB response (14:08) - COO scope and business operations structure (16:08) - Hiring a trained psychologist for HR (18:49) - Open source culture and user feedback (22:03) - Commercializing with the 1-2-3 framework (25:05) - Generative AI as an opportunity (28:32) - Bottom up enterprise sales motion (31:14) - Hybrid KPIs, OKRs, and quarterly planning (34:54) - Crazy story, a 10 month logo negotiation (41:01) ### Mentioned in This Episode - Nitin Gupta on LinkedIn - Prisma: Nitin's company, the open source ORM discussed throughout - Scandit: Nitin's previous company in the logo negotiation story - Automattic: Michael's former company with its own hackathon culture - Heroku: Adam Gross of Heroku popularized the 1-2-3 framework - Twilio: Billboard example of developer led bottom up adoption - Billions: TV show that inspired the staff psychologist idea --- ## Shanaz Hemmati, ZenBusiness COO on Building $1.7B Co. URL: https://betweentwocoos.com/zenbusiness-coo-shanaz-hemmati-on-building-a-1-7b-company-that-thrives-in-both-u/ Published: 2023-09-11 ### Summary Join us as we chat with Shanaz Hemmati, the COO of ZenBusiness, who gives us a fascinating insight into the workings of a public benefit corporation that generates more than $100M in ARR. Listen to her as she speaks about the various initiatives and programs that ZenBusiness undertakes to give back to the community and society. From a grant program to support their customers to her role evolution from CIO to COO, Shanaz’s experiences shed light on the strategies they use to navigate their responsibilities within a small team. In this chat, we also explore the potential of generative AI to increase speed, accuracy, scalability, complexity, and accessibility of structured language, and how ZenBusiness leverages this to expand capacity. From discussing the importance of data protection to understanding the potential threats to businesses, Shanaz provides a comprehensive overview of the operations side of the company, including their customer support in the contact center. Shanaz also talks about the company’s organizational structure, with CTO, HR, customer success, legal, program management, procurement, and corporate citizenship all reporting to her. Learn about the process of hiring great people, and how her passion and love for what she does is the key to success. She also shares her experiences with M&A, and how she and her team at HomeAway used the strategy of acquiring existing vacation rental services to make the company global. From tracking the macroeconomic environment to discussing the advantages of remote working, Shanaz provides a wealth of information for anyone interested in understanding the workings of a successful business. ### Topics Covered - Shanaz's path from HomeAway to ZenBusiness (0:11) - Public benefit corporation and customer grants (1:13) - Evolving from CIO to COO (5:19) - Testing manually before building automation (7:42) - Generative AI and customer data protection (9:32) - Using AI to expand support capacity (13:52) - Org structure under the COO and CEO (15:50) - Hiring passionate people and a jerkless environment (18:42) - HomeAway M&A and integration lessons (21:23) - Engineering roots shaping operations (25:53) - What drove nine-figure revenue growth (28:04) - Staying close to customers at scale (29:53) - Tracking KPIs with Salesforce and Tableau (32:59) - Going remote and hiring across 30 states (38:00) ### Mentioned in This Episode - Shanaz Hemmati on LinkedIn - ZenBusiness: Shanaz's company, platform for starting small businesses - HomeAway: Shanaz's prior company, taken public, now part of Vrbo - ChatGPT: Discussed for prompting, policy, and expanding operations capacity - Salesforce: The CRM ZenBusiness uses to track KPIs - Tableau: Reporting tool ZenBusiness adopted for data insights - Trustpilot: Where ZenBusiness holds a 4.9 star rating --- ## Munish Gandhi, Productiv COO on AI for SaaS Cost Cuts URL: https://betweentwocoos.com/productiv-coo-munish-gandhi-on-harnessing-ai-for-streamlining-contract-renewals/ Published: 2023-08-01 ### Summary Join me and our guest, Munish Gandhi, co-founder and COO of Productiv, as we unravel the intricacies of SaaS governance and optimization. We talk about how the rapid growth of SaaS applications, fueled by a wealth of funding, has led to a lax approach to purchasing and implementing applications. Munish expertly guides us through the function of Productiv, explaining how it provides valuable insights and recommendations for SaaS portfolio governance, rationalizing SaaS spending, and refining SaaS procurement. We also delve into the issue of SaaS underutilization, considering how incentives from SaaS companies, the excitement of software purchases, and the mismatch between what people need and what is purchased can lead to high costs and underutilization. Listen in as we explore the application of generative AI in streamlining contract renewals and procurement with Munish. Our conversation uncovers how AI can automate the procurement process and enhance workflow, shedding light on how Productiv's product can help educate everyone involved in the software buying process. We then discuss Munish's journey to his COO role and how his previous experience at LinkedIn influenced his approach to building a software company. We also consider the challenges of selling a product that doesn't contribute to top-line revenue and discuss the objective of creating a platform that helps people be more Productiv in their roles. Munish also shares his experience with crisis management and decision-making, emphasizing the importance of communication and risk management during turbulent times. He offers a glimpse into his method of gathering data from other founders and investors to make informed decisions. This conversation provides valuable insights into how to approach decision-making when faced with an imperfect amount of information. This episode is packed with wisdom and strategies for managing SaaS applications, making it a must-listen for anyone navigating the modern software landscape. ### Topics Covered - Meet Munish Gandhi and Productiv (0:13) - The SaaS explosion and lax governance (1:32) - Putting numbers on SaaS underutilization (3:55) - Too many licenses and duplicate tools (4:48) - Governance and compliance at the point of entry (7:29) - Shadow IT, freemium tools, and visibility (9:52) - How AI fits into SaaS oversight (11:59) - Generative AI for contract renewals (14:56) - Automating procurement across stakeholders (18:09) - Spreadsheets, renewals, and offboarding risk (21:01) - The accidental founder's path to COO (22:31) - Selling software that does not drive revenue (24:38) - Corporate lessons from LinkedIn (28:59) - The SVB crisis and deciding in an hour (34:19) ### Mentioned in This Episode - Munish Gandhi on LinkedIn - LinkedIn Sales Navigator: Munish's charter was making it a standard B2B product - Gartner: Michael cites its 195 billion dollar SaaS forecast - Asana: Michael's example of removing 40 unused seats - Silicon Valley Bank: The bank collapse behind Munish's crisis management story - OpenAI: ChatGPT shadow IT example including Samsung's code leak --- ## Allen Narcisse, Gigs CEO on Labor Markets & AI Jobs URL: https://betweentwocoos.com/former-workrise-coo-and-current-ceo-of-gigs-allen-narcisse-on-transforming-the-l/ Published: 2023-07-18 ### Summary Join us as we sit down with Allen Narcisse, former COO at Workrise and co-founder and CEO of Gigs, for an enlightening conversation about his journey in the gig economy. Allen takes us through his career trajectory, starting from his initial venture, eBuyLine, to his stints building Uber and Lyft, and finally, to his current venture, Gigs. Listen in as Allen shares valuable insights on building marketplaces, the importance of a great first impression, and the inspiration behind Gigs. In the second part of our discussion, we explore the intricacies of operating a gig economy platform. Allen shares the three-step process Gigs uses to source jobs and engage job seekers and the crucial role of having a team with previous founders, Lyft, and Uber DNA. He also shares his perspective on prioritization and ensuring the team has the resources and talent to accomplish winning moves. In the final part of our conversation, we discuss the future of the labor market in the face of automation and AI. Allen shares his thoughts on the need for job seekers to be equipped with the right information and tools to navigate the changing job market. Tune in to hear more about Gigs’ business model, the cost per application model, and how it ensures employers only pay for qualified applicants. Finally, we touch on the implications of automation on the labor force and the need for better communication between employers and workers. ### Topics Covered - Introducing Allen Narcisse and Gigs (0:11) - From Ebyline to Uber Eats, Lyft, and Workrise (1:04) - Why hourly job seekers are underserved (5:21) - Cold starting the Gigs marketplace (8:19) - Team DNA and running at the biggest problem (10:33) - Operating as a CEO after being a COO (12:31) - Designing company values before founding (16:16) - Psychological safety and balanced meetings (20:42) - Making only five percent of decisions (24:46) - Balancing doing versus leading (29:28) - Filling 80 million hourly roles (32:59) - Cost per application business model (34:43) - Automation, AI, and the labor market (37:31) - An inspector call in week three at Uber Eats (41:06) ### Mentioned in This Episode - Allen Narcisse on LinkedIn - Gigs: Allen's company matching hourly job seekers with neighborhood jobs - Workrise: Energy labor marketplace where Allen served as COO - Uber Eats: Allen led West Coast operations as Eats grew 45x - Lyft: Allen grew drivers and balanced rideshare markets - The Cold Start Problem: Andrew Chen book on marketplace cold start strategy - Ebyline: Allen's first startup connecting freelance journalists with publishers - Georgetown Center on Education and the Workforce: Source of the 23 million COVID job losses figure --- ## Tobias Peggs, Square Roots CEO on Urban Indoor Farming URL: https://betweentwocoos.com/embracing-the-future-of-food-the-rise-of-sustainable-indoor-urban-farming-with-s/ Published: 2023-06-27 ### Summary Can we really grow sustainable, delicious, and healthy food right in the heart of a bustling city? In this eye-opening episode, I had the pleasure of chatting with Tobias Peggs, co-founder and CEO of Square Roots, an innovative indoor urban farm tech company that's revolutionizing how we grow and distribute food in urban areas. Together, we explored the intricate operations of creating a successful indoor urban farm, from engineering and construction to farming and distribution processes. Tobias shared fascinating insights on how Square Roots uses cutting-edge technology to minimize its environmental impact, reduce its carbon footprint, and produce food sustainably despite the challenges posed by climate change. We also touched upon the importance of staying true to a company's mission and values, as well as how Square Roots navigated the COVID-19 pandemic and adapted their business to continue providing fresh, nutritious, and mouth-watering produce to their community. Don't miss this thought-provoking conversation on the future of urban agriculture and how it can help us tackle some of the most pressing global issues of our time. ### Topics Covered - Introducing Tobias Peggs and Square Roots (0:15) - Why climate change demands a new farming model (1:41) - Unpacking the full stack farming operation (3:30) - The hidden complexity of growing food (8:12) - Taking a software MVP approach to farming (9:35) - Dividing responsibilities with COO Amanda Lufkin (12:16) - Inside the grow zones and head house (15:59) - Partnering with Gordon Food Service on distribution (19:10) - Taking on big agribusiness and crop economics (22:26) - Measuring and reducing the carbon footprint (25:25) - The Square Roots Playbook and rolling OKRs (30:18) - Losing every restaurant customer overnight in the pandemic (33:46) - Where to follow Square Roots (37:23) ### Mentioned in This Episode - Tobias Peggs on LinkedIn - Gordon Food Service: Distribution partner hosting Square Roots farms at its centers - Watershed: Measured the CO2 emissions of Square Roots' full footprint --- ## Stephan Jacob, Cotopaxi COO on $100M Brand Building URL: https://betweentwocoos.com/cotopaxi-coo-cofounder-stephan-jacob-on-getting-to-100m-in-revenue-brand-buildin/ Published: 2023-05-02 ### Summary Stephan Jacob, Co-founder and COO of Cotopaxi, joins Michael to talk about building an impact-driven business, how sustainability drives Cotopaxi’s product development, managing a CEO transition, the proliferation of certified B Corps, donating revenue to fight poverty in developing countries, brand building and taking on North Face and Patagonia, and taking llamas on college campuses. With a humanitarian-drive and strong business acumen, Stephan’s career in the COO seat began at Cotopaxi, following the sale of his company, Kembrel in 2013. During this time, Stephan reconnected with an old University of Pennsylvania Wharton and Lauder Institute classmate, Davis Smith, with the commitment to build a brand for those who shared their values: a deep-rooted interest in giving back and a passion for the outdoors. From there, came Cotopaxi, an outdoors brand, which has never wavered from its ESG principles and humanitarian focus. Under Stephan’s stewardship, Cotopaxi has become a role model for how businesses can achieve the seemingly at-odds goals of making the world a better place while achieving growth. As a B-Corp using environmentally friendly sourced materials and ethically-sourced labor, Cotopaxi’s values and colorful apparel have struck a chord with its customers, generating $100m in revenue, aiding 1.5 million people in poverty, and assisting 90k refugees throughout South America in 2021 alone. ### Topics Covered - Introducing Stephan Jacob and Cotopaxi (0:11) - Origin story from Wharton to founding Cotopaxi (1:12) - Microentrepreneurship as a model for fighting poverty (5:53) - 2021 impact numbers and mission driven talent (8:58) - Brand building with repurposed and recycled materials (13:47) - A direct line between makers and consumers (19:37) - Benefit corporations versus B Corp certification (20:49) - Nespresso and B Corp legitimacy questions (24:04) - Growth lessons and catching up back of house (30:00) - Communicating impact values to a distributed team (35:47) - CEO transition from Davis Smith to Damien Huang (39:39) - Spotting Cotopaxi gear in the wild (45:18) - Llamas on campus and the first Questival (48:19) ### Mentioned in This Episode - Stephan Jacob on LinkedIn - Cotopaxi: Stephan's outdoor gear brand built to fight poverty - 1% for the Planet: Cotopaxi pledges 1% of revenue to environmental causes - Ego Is the Enemy: Ryan Holiday book Stephan cites on founder ego - Forerunner Ventures: Kirsten Green's firm led Cotopaxi's seed round - Bain Capital: growth investor that reset what success looks like - The Lauder Institute: Wharton program where Stephan and Davis Smith connected - Questival: Cotopaxi's 24 hour adventure race that launched the brand --- ## Woody Hartman, Lime COO on Micromobility & Scaling Lyft URL: https://betweentwocoos.com/lime-coo-woody-hartman-on-micromobility-helping-lyft-grow-from-100k-to-3b-in-rev/ Published: 2023-04-10 ### Summary Woody Hartman, COO of Lime and former VP of Global Operations at Lyft, sits down with Michael to talk about the challenges in scaling a micro-mobility company, how Lime’s gained a competitive advantage over other players in the market, and why he chose to climb Mount Everest following his time at Lyft! A biz ops wizard, Woody’s career started as a Business Analyst at McKinsey in 2006, focused on M&A and private equity due diligence. With a passion for creating joyful customer experiences, Woody jumped to the gaming and entertainment website IGN, leading corporate strategy before attending Stanford University’s Graduate School of Business, where he was amongst the top students, earning him distinction as a Siebel Scholar. Following a short stint at Disney as a Global Development Associate for Imagineering, Woody joined Lyft in February 2013 as employee 34. Initially tasked with leading Lyft’s launch in Los Angeles, just the company’s second market, Woody mastered these rollouts, becoming the company’s VP of Global Operations in September 2017. ### Topics Covered - Introduction and Woody's winding path to the COO seat (0:10) - Building the Lyft launch playbook through experimentation (5:11) - 24 launches in 24 hours and driver supply (8:14) - Adaptability, humility, and lessons from McKinsey (12:15) - Building culture at Lyft, TeamSnap, and Lime (17:16) - Coaching by guiding people to their own answers (21:40) - Succession planning and leaving Lyft after the IPO (25:55) - Dividing responsibilities with Lime CEO Wayne Ting (28:35) - Equity zones and partnering with cities (30:33) - The energy case for micromobility and right-sized vehicles (33:34) - Growth through focus and reaching EBITDA positive (38:38) - Scooter congestion and reallocating street space (44:46) - Launching New York City in 15 days (48:45) - Summiting Mount Everest and coming back down (51:44) ### Mentioned in This Episode - Woody Hartman on LinkedIn - Lime: The micromobility company Woody leads as COO - Lyft: Woody helped scale revenue from $100k to $3 billion - TeamSnap: Sports software company Woody led after leaving Lyft - McKinsey & Company: Woody's first job in strategy consulting - Disney: Woody's employer when Lyft recruited him as employee 34 --- ## Flick Fisher on Data Privacy & GDPR at Fieldfisher URL: https://betweentwocoos.com/data-privacy-gdpr-with-flick-fisher-partner-at-fieldfisher/ Published: 2023-01-23 ### Summary On this week’s episode, Michael’s joined by Felicity “Flick” Fisher, Partner and de facto COO of the law firm, Fieldfisher. Flick breaks down all things privacy and data related, including the European Union’s General Data Protection Regulation, where privacy and data laws may be headed, and the impact privacy advocates have had on the space. Now amongst the top InfoSec legal experts, Flick’s journey in the space began when she moved to the Bay Area in 2015. Initially joining her firm, Osborne Clark’s, Palo Alto office to focus on transactions in the tech industry, her move coincided with the emerging push for increased data privacy regulations. In January 2016, Flick moved to Fieldfisher as an Associate and the fourth employee of its newly formed Privacy, Security, and Information Group, immersing herself in all data privacy matters, with a particular interest in EU compliance as the GDPR was implemented. Since then, Flick has become a Partner, stepping into a de facto COO role, and overseeing the firm's day-to-day operations. ### Topics Covered - Introducing Flick Fisher and her path into privacy (0:11) - Scaling, recruiting, and managing a remote team (4:16) - Building a client base through word of mouth (11:23) - GDPR explained in thirty seconds (13:40) - Max Schrems and accelerating GDPR enforcement (14:54) - Privacy Shield invalidation and Standard Contractual Clauses (19:53) - Transfer restrictions and whether startups should retreat (24:13) - Prospects for a Privacy Shield 2.0 agreement (30:14) - Ireland's preliminary decision on Meta data transfers (32:11) - Country regulators and the Google Analytics ruling (36:43) - Beyond GDPR, the Data Act and ePrivacy Directive (39:28) - Should you design for strict German requirements (41:21) - Operationalizing GDPR as controller or processor (44:15) - Resources for staying current on GDPR (49:11) ### Mentioned in This Episode - Flick Fisher on LinkedIn - Fieldfisher Privacy Blog: Recommended resource for privacy and GDPR updates - GDPR: Full text of the EU regulation discussed throughout - Irish Data Protection Commission: Meta's lead EU regulator weighing a transfer suspension - Google Analytics: Austrian regulator ruled its use violates GDPR --- ## Holger Seim, Blinkist CEO on 21M Users & the 4-Day Workweek URL: https://betweentwocoos.com/blinkist-co-founder-ceo-holger-seim-on-growing-to-21m-users-optimizing-your-info/ Published: 2023-01-16 ### Summary Holger Seim, co-founder, and CEO of Blinkist, speaks with Michael about how Blinkist emerged out of shifting consumption patterns, where the company may be headed in the future, and how to stay true to your long-term strategic vision while also incorporating the thoughts and ideas of other stakeholders. With an entrepreneurial spirit that emerged during his childhood in Germany, Holger’s journey has been guided by his unsatiated love of building things from the ground up. Leaning further into this spirit in college, Holger founded a successful student consultancy with several friends. Upon graduating in 2010, Holger joined T-Mobile, working in the Division of the CEO. While he valued his experience and time working close to leadership, the hunger to build his own company drew him to join his college friends in Berlin. Recognizing that they lacked the time they once had as college students to quickly read books in full, Holger and his team founded Blinkist in 2012. ### Topics Covered - Introducing Holger Seim and Blinkist (0:09) - From student consultancy to founding Blinkist (1:31) - Corporate learning demand and Blinkist for Business (5:39) - Competing with Amazon and winning over publishers (8:52) - Keeping users engaged in the attention economy (14:25) - Hearing no from VCs and proving the market (21:33) - Adding audio as the biggest game changer (26:01) - Expanding from Germany into the US market (28:55) - Learning to lead and building a support network (31:58) - Designing a VP-level leadership team and co-CTOs (36:08) - Keeping the vision intact across 170 employees (40:28) - A blackmail attempt from a fake lawyer (45:06) - Piloting a summer 4-day workweek (48:51) - Update on the 4-day workweek experiment (54:56) ### Mentioned in This Episode - Holger Seim on LinkedIn - Entrepreneurs' Organization: Holger's monthly peer forum and support network - Babbel: board mentor Markus Witte's company, also a market sizing example - Insight Partners: Blinkist investor whose board member was an operator CEO - Kettle: previous guest Nathaniel Manning's process without bureaucracy line - Workrise: Elliot Darvick, who submitted the audience question, works there - TechCrunch Disrupt: 2014 conference where audio feedback sparked the pivot --- ## Diego Camberos, Vodafone Qatar COO on 5G & World Cup Prep URL: https://betweentwocoos.com/vodafone-qatar-coo-diego-camberos-on-prepping-for-1-4m-world-cup-visitors-rollin/ Published: 2022-11-07 ### Summary Diego Camberos, COO of Vodafone Qatar and former CEO of Tigo Millicom Senegal and Rwanda, joins Michael to share insight into navigating cultural differences in different markets, how “radical simplification” has served as the bedrock of Vodafone’s success, and how to build a corporate culture that acknowledges and respects different cultures. A citizen of the globe, having spent time living in several countries outside his home country of Bolivia, Diego has expertise across various departments, ranging from operations to marketing to commercial strategy. Starting his career in the quick service restaurant (QSR) industry upon returning to South America after college in the US, Diego served as the Operations Manager for McDonald’s Columbia. He led day-to-day operations for the company’s McOpCo chain from 2003 to 2005. After a brief stint as Burger King’s Director of Operations for the Dominican Republic, Diego shifted his attention to the telecommunications industry, starting his journey in the space as the Vice President of Sales for Trilogy/Viva Dominicana in 2007. In 2009, Diego joined Swedish telco giant Millicom as the Head of Sales & Marketing for its Tigo brand, rising to the role of CEO of its Rwanda market in 2011. Following a successful tenure as the CEO of Tigo/Millicom’s Senegal business, Diego headed further east in March 2017, signing on as Vodafone Qatar’s Consumer Business Unit Director before taking the reins as its COO in March 2018. ### Topics Covered - Introducing Diego Camberos of Vodafone Qatar (0:11) - Diego's path to the COO role (1:14) - Adapting to cultural norms in each market (4:17) - Building one culture across 67 nationalities (7:25) - Vodafone lessons in quality and data discipline (10:32) - Practice sharing across Vodafone Group markets (12:12) - Scope of the COO role in Qatar (15:44) - Radical simplification behind 25% revenue growth (17:20) - No compromise on quality, KPIs over buzzwords (21:47) - Measuring every customer touch point (26:59) - Two years of World Cup network preparation (30:07) - Rolling out 5G and broadcasting the games (32:31) - 16,000 daily arrivals and country-scale logistics (35:47) - Group A loyalties and a Rwanda story (39:20) ### Mentioned in This Episode - Diego Camberos on LinkedIn - Vodafone Qatar: Diego's company, preparing Qatar's network for the World Cup - Vodafone Group: Practice sharing and talent leverage across group markets - Millicom (Tigo): Diego's prior company, CEO in Rwanda and Senegal - McDonald's: Diego's example of a strong global corporate culture - FIFA World Cup Qatar 2022: The tournament driving two years of network preparation --- ## Cameron Herold on Founding COO Alliance & Antarctica URL: https://betweentwocoos.com/silent-discos-with-penguins-in-antarctica-founder-of-the-coo-alliance-and-former/ Published: 2022-10-27 ### Summary Cameron Herold, Founder of the COO Alliance and former COO of 1-800-GOT-JUNK, talks to Michael about building a successful company culture, effective process implementation, and what a strong relationship between a COO and CEO should look like. They also touch on how to attract “A” players to your team,  how to approach each initiative with a Plan, Brief, Execute, and Debrief mentality, reverse engineering processes, and of course, penguins. Cameron is a growth expert and an acclaimed “CEO Whisperer”, who has led several companies, focusing on people and process improvement. In 2000, Cameron was brought aboard as the COO of 1-800-GOT-JUNK?, leading operations, P&L, franchise development, and sales amongst other responsibilities. He helped grow 1-800-GOT-JUNK? from 12 franchises and $2 million in revenue to 300 franchises across 4 countries and $150 million in revenue when he departed in 2007. Since then, he’s written 5 books and serves as an independent consultant for several major companies. Upon realizing there was no group for COOs to learn and share their knowledge, Cameron founded the COO Alliance in 2016 as a network for COOs to exchange ideas and best practices. ### Topics Covered - 1-800-GOT-JUNK growth metrics recap (1:09) - Building company culture that scales (1:36) - Recruiting A players who are not job hunting (3:11) - Avoiding a homogeneous culture (6:25) - Evaluating new hires and giving praise (7:30) - Building processes from scratch at Got Junk (10:29) - Training people to help themselves (14:45) - World-class training at a tech company (15:26) - Process without bureaucracy (18:10) - Reverse engineering goals into systems (20:29) - The Plan, Brief, Execute, Debrief cadence (22:48) - Becoming the CEO Whisperer (27:35) - The CEO and COO relationship (29:36) - Taking 65 executives to Antarctica (35:11) - Crazy story: silent disco with penguins (39:36) --- ## Cathy Hawley on Building Great Company Culture URL: https://betweentwocoos.com/return-path-chief-people-officer-co-author-of-startup-cxo-bolster-co-founder-cat/ Published: 2022-10-18 ### Summary Cathy Hawley, former Chief People Officer of Return Path and Co-Founder of Bolster, sits down with Michael to discuss the importance of intentionality and an agile mindset in building a remote company culture, how people operations grew out of traditional human resources, and why employers should focus on a co-creating mentality when approaching its workforce. Cathy is a strategic people leader, with an exceptional track record of laying the foundation for strong company cultures. After several years in the UK as a social services counselor, Cathy returned to the US as a human resources director. With her experience in the UK informing her people-centric approach to human resources, Cathy served as the Sr. Director of Human Resources at Epsilon for several years before joining Return Path as its Sr. People Director in 2008. Rising through the ranks to become the company’s Chief People Officer, Cathy fostered a strong partnership with Matt Blumberg, Return Path’s CEO, which was instrumental in helping the company build a development-focused culture. After departing Return Path in June 2019, Cathy teamed back up with Matt in 2020 to found Bolster, an executive talent marketplace, and to co-author Startup CXO: A Field Guide to Scaling Up Your Company's Critical Functions and Teams. ### Topics Covered - Introducing Cathy Hawley and Bolster (0:09) - People operations versus traditional HR (2:45) - How Return Path built its culture (7:37) - Hiring people leaders from day one (10:05) - Agile mindset for remote culture (12:24) - The CEO and chief people officer partnership (16:05) - Bolster's founding story and eight co-founders (18:41) - Iterating values and becoming mostly self-managed (22:38) - The Great Resignation and shifting employee power (24:49) - Treating employees like volunteers (28:28) - Titles, levels, and career development (32:46) - Writing the Startup CXO field guide (37:16) - A humane approach to reorganization (39:51) - Advice for starting at a new company (42:52) ### Mentioned in This Episode - Cathy Hawley on LinkedIn - Startup CXO: Field guide Cathy co-authored on scaling company functions - The First 90 Days: Book Cathy recommends for anyone starting a new role - Return Path: Cathy's home for 11 years, acquired by Validity --- ## Dale Pfeifer, Goodworld CEO on Social Impact & CSR URL: https://betweentwocoos.com/goodworld-ceo-dale-pfeifer-on-scaling-social-impact-via-tech-mastercard-citi-bla/ Published: 2022-08-02 ### Summary Dale Pfeifer, CEO of Goodworld, chats on scaling social impact through tech, the evolution of CSR (corporate social responsibility) from consumer targeted to greater corporate involvement, Mastercard, Citi, and BlackRock's leadership in CSR, the impact of the pandemic on accelerating CSR, the challenges of raising VC capital as a woman and as a social impact co., and what it's like to pitch President Obama & being on the front page of the NYTimes. Goodworld helps companies grow by making it easy to embed Social Impact into commerce, workplace culture and sustainability initiatives. Through our Social Impact experiences, sales teams close more deals at higher prices, HR teams increase employee engagement and attract talent, ESG teams drive ROI from their activities, and marketing teams create irresistible brands that boost product prices. Dale Pfeifer is passionate about Social Impact, CSR and ESG. Dale is the founder and CEO of fintech Goodworld - named one of the World’s Most Innovative Companies and a World Changing Idea by Fast Company magazine. Their Social Impact Platform empowers employees, customers and communities to drive positive cultural change together through giving, volunteering and rewards. ### Topics Covered - Introducing Dale Pfeifer and Goodworld (0:11) - From New Zealand nonprofit work to hashtag donations (1:28) - Rapid platform growth and the Cheerful Giving acquisition (4:31) - The evolution of corporate social responsibility (6:25) - Mastercard, Citi, and employee-driven giving (9:19) - How the pandemic accelerated corporate giving (11:41) - Goodworld's go-to-market mix of inbound and outbound (14:25) - Dividing responsibilities with COO John (16:03) - Fundraising as a woman and social impact founder (17:53) - Mastercard's values-driven investment in Goodworld (22:41) - Future bets on ecosystems, gift cards, and crypto (24:58) - What Goodworld got right (28:13) - Lean Startup advice for entrepreneurs (31:36) - Pitching President Obama and the New York Times (33:25) ### Mentioned in This Episode - Dale Pfeifer on LinkedIn - VAX LIVE: Goodworld powered the online giving site for this concert - Business Roundtable: Its 2019 stakeholder statement marked a CSR turning point - 1776: Incubator and early investor where Dale pitched President Obama - The New York Times: Dale's Obama pitch ran on the front page, July 2014 - Mastercard: Lead investor in Goodworld's second round and CSR leader --- ## Jenny Lawton on Makerbot's $400M Exit & Techstars Ops URL: https://betweentwocoos.com/bolster-evp-fmr-makerbot-ceo-techstars-coo-cio-jenny-lawton-on-makerbots-400m-ex/ Published: 2022-06-14 ### Summary In this episode, Michael Koenig speaks with Jenny Lawton, EVP at Bolster, about MakerBot's $400 million exit, scaling Techstars, and bringing order to chaos as a COO. Jenny traces her path from teenage babysitting entrepreneur to roles across the C-suite, and explains why simple operating systems and a Montessori-style box of rules give teams freedom to move faster. The conversation covers MakerBot's $10 million Foundry Group round, the culture conflict that followed venture funding at an open-source company, and the Stratasys acquisition roughly 18 months later. Jenny also describes scaling Techstars from 15 to 55 accelerators across 15 countries, the accelerator effect that flips the 80/20 startup failure rate, the Give First philosophy, and why women founders are judged on outcomes while men are judged on potential. ### Topics Covered - Path to Bolster through Matt Blumberg and Brad Feld (1:54) - Teenage businesses from babysitting to logo design (4:19) - Bringing order to chaos as a COO (5:45) - Simple operating systems and advice for new COOs (7:29) - Montessori method applied to business operating systems (9:30) - CEO versus COO and serving first-time CEOs (12:20) - MakerBot's $400M exit and culture lessons (16:34) - Resolving mission misalignment through transparency (19:35) - Techstars overview and the Give First philosophy (21:58) - Scaling Techstars from 15 to 55 accelerators (25:06) - Sphero, Disney, and flipping startup failure rates (29:52) - Unconscious bias facing women entrepreneurs (32:40) - Advice for the next generation (38:13) - Caregiving and flipping the work-life balance (39:59) ### Mentioned in This Episode - Jenny Lawton on LinkedIn - MakerBot: Desktop 3D printing company Jenny led to its exit - Stratasys: Acquired MakerBot for over $400 million - Techstars: Global accelerator where Jenny was COO and CIO - Foundry Group: MakerBot's $10 million investor, Brad Feld's firm - LittleBits: STEM learning company where Jenny served as COO - Sphero: BB-8 maker whose Disney accelerator run changed the business --- ## Jonathan Stull on Building a $3.5B Marketplace at Handshake URL: https://betweentwocoos.com/handshake-coo-jonathan-stull-on-democratizing-access-to-opportunity-the-journey/ Published: 2022-06-01 ### Summary Handshake COO, Jonathan Stull, joins to talk about the journey of building a three-sided marketplace to $100M ARR at a $3.5B valuation with over 500 employees. We touch on the role of COO at Handshake; Jonathan's path from waiting tables to Capital Hill to PE to tech; compromising on tactics but not on vision or mission; adding independent board members; deploying $100MMs in funding; the move from hiring generalists to specialists; global expansion; timing and more. Handshake’s mission is to democratize access to opportunity: to help every student find the right job, no matter where they’re from or who they know. Today, Handshake is the number one site for college students to find jobs. Handshake powers career offices at 1,300+ higher ed institutions—including 100+ community and technical colleges. With 550,000+ employers recruiting on Handshake—from every Fortune 500 company to nonprofits, startups, and more—schools that join Handshake see on average a 3x increase in the size and diversity of their employer network. ### Topics Covered - Introduction and Handshake's growth numbers (0:10) - Jonathan's winding path from waiting tables to COO (1:36) - Wearing every hat from product to legal (5:50) - What Handshake got right while scaling (10:19) - Solving the three-sided marketplace chicken and egg (15:45) - Why the timing was right for Handshake (21:04) - Moving from generalists to specialists (26:05) - Deploying $200 million in fresh funding (30:48) - Choosing countries for global expansion (34:42) - Evolving the operating system and OKRs (38:36) - Adding independent board members (42:20) - Diversity in product, team, and capital stack (45:41) - Sleeping in college dorms at NACE (50:23) ### Mentioned in This Episode - Jonathan Stull on LinkedIn - UNCF: Dr. Michael Lomax, its CEO, joined Handshake's board - Base10 Advancement Initiative: Black-led growth fund directing returns to HBCU scholarships - Give Away Your Legos: Molly Graham's scaling article Jonathan says gets referenced constantly - NACE: Conference where the early team slept in dorms - Flipboard: Jonathan did business development there before Handshake - Lookout: Mobile security startup where Jonathan started in tech - Actis: Emerging markets private equity firm where Jonathan invested --- ## Cyrus Mistry, GoGuardian COO on Google to Startup Jump URL: https://betweentwocoos.com/goguardian-coo-cyrus-mistry-on-joining-at-the-same-time-as-200m-in-new-funding-s/ Published: 2022-05-02 ### Summary GoGuardian COO, Cyrus Mistry, spent 14 years at Google as the Director of Product Management for Chromebooks bringing computers to schools, before joining GoGuardian as COO right when they raised $200M in new funding from Tiger Global Management. Cyrus has a wealth of knowledge not only stemming from his four advanced degrees but also from his operating experience at Disney prior to Google. Have a listen to hear about his story and what it's like to move from Google to a startup. ### Topics Covered - Introducing Cyrus Mistry and GoGuardian (0:11) - From developer to product manager to COO (1:27) - GoGuardian's mission and products (2:52) - Carving out the COO role (4:00) - Joining as the Tiger Global round closed (4:51) - Why leave Google for a startup (6:36) - Learning that 80 percent of the job is people (8:58) - What to bring from Google, Disney, and airlines (11:43) - Redesigning promotion ladders to remove bias (15:27) - Scaling engineering and holding the hiring bar (18:18) - Paying to retain talent in a hot market (20:26) - Deploying $200M in organic growth and M&A (21:33) - Bringing bricked Chromebooks back from a cruise (24:15) ### Mentioned in This Episode - Cyrus Mistry on LinkedIn - Tiger Global Management: Invested $200M weeks after Cyrus joined - Chromebooks: Cyrus launched Chromebooks for education at Google - The Walt Disney Company: Prior operating experience and park operations contrast - Johns Hopkins University: Where Cyrus earned his four degrees --- ## Art Harding, People.ai COO on Operating Leadership URL: https://betweentwocoos.com/people-ai-coo-art-harding-on-supporting-ukrainian-team-members-e2t-driving-effic/ Published: 2022-04-11 ### Summary In this episode, Michael Koenig speaks with Art Harding, COO at People.ai, about how the revenue intelligence company prepared for Russia's invasion of Ukraine and supported its Ukrainian team members. Art describes the early warning signals the leadership team acted on, the relocation options offered to employees months before the conflict began, and the clear division of leadership roles that kept the business running while colleagues made difficult personal decisions. Art also lays out E2T, his three-part mandate for operations teams: drive efficiency, improve effectiveness, and transform the business for the future. He explains why inspection without coaching is micromanagement, why sales and marketing should move past alignment toward integration, and why a product is not truly released until its first three customer references exist. Operations leaders looking for a clear charter for their function will find one here. ### Topics Covered - Introducing Art Harding and People.ai (0:00) - How People.ai supported its Ukrainian team members (1:00) - Employee relocation options months before the conflict (4:39) - Meeting People.ai's CEO as a New Relic customer (7:52) - Default timeframes and communicating like a symphony (10:59) - From sales and marketing alignment to integration (13:46) - What healthy friction looks like (17:24) - Art's path from services to COO (22:32) - Product led growth versus sales led growth (25:41) - Preparing go to market for product launches (29:37) - E2T: driving efficiency, effectiveness, and transformation (33:13) - Inspection without coaching is micromanagement (36:51) - Advice for first time COOs (41:43) - Joining People.ai the quarter COVID started (44:08) ### Mentioned in This Episode - Art Harding on LinkedIn - New Relic: Where Art met People.ai's CEO as a customer - Riverbed: PE acquisition there moved Art into sales operations --- ## Angela Tucci, Uplight COO on $1.5B Valuation & B Corps URL: https://betweentwocoos.com/uplight-coo-fmr-symantec-cso-angela-tucci-on-reaching-a-1-5b-valuation-in-3-year/ Published: 2022-03-17 ### Summary Angela Tucci, COO at Uplight, joins to talk about running a $1.5B company created from the M&A of 6 companies, advocating for voice & equity for women in the workforce, finding an inspiring CEO, working with utility companies to reduce their carbon footprint, taking private equity vs. VC funding, integrating acquisitions remotely during covid, the impact of politics, and systems thinking. Prior to Uplight, Angela was Chief Strategy Officer at Symantec, Chief Revenue Officer and Chief Marketing Officer at Rally Software, and Chief Executive Officer at Apto, so she's a clear underachiever. :) Uplight is a technology partner for energy providers and the clean energy ecosystem to help them reach their decarbonization goals.  Uplight was last valued at $1.5 billion dollars, which is an achievement in and of itself, let alone for a company that's only 3 years old. ### Topics Covered - Introduction and Angela's path to Uplight (0:10) - What B Corp certification means (3:05) - Dividing the work with CEO Adrian (5:33) - How Uplight helps utilities decarbonize (9:03) - Merging six companies into Uplight (13:11) - Choosing private equity over venture capital (15:23) - Blending six company cultures (17:07) - Integrating remotely during COVID (19:14) - Selling to 80 regulated utilities (23:36) - The 90 month climate countdown (28:45) - Systems thinking advice for COOs (33:37) - Anita Borg Institute and women in tech (36:01) - Building psychological safety and diversity (39:48) - A diversity blind spot on her watch (44:39) ### Mentioned in This Episode - Angela Tucci on LinkedIn - Anita Borg Institute: Angela chairs its board of trustees - B Corp Certification: Uplight's certification, business as a force for good - Symantec: Where Angela served as Chief Strategy Officer - AES: Fortune 500 strategic investor that rolled into Uplight --- ## Ken Weary, Hotjar COO on Remote-First Culture & M&A URL: https://betweentwocoos.com/hotjar-coo-ken-weary-on-remote-first-with-220-employees-creating-remote-culture/ Published: 2022-03-09 ### Summary Ken Weary is the COO of Hotjar and joins to chat on running a fully remote 220 person company, being a digital nomad traveling for over 7 years as a COO with a family, going through M&A and diligence on the buyer, always having a just cause as the "why" behind what you do, the impact of remote on the great resignation, and bringing the Houses from Harry Potter to the workplace. Hotjar, is a European headquartered start-up with over 200 fully remote team members distributed across the globe. Ken is also a digital nomad and has been traveling with his family across Central America, Europe, and Africa for nearly 7 years. Prior to his travels, Ken held leadership positions in traditional corporate environments where he gained great experience but was tied to his desk. He relishes life “outside the cube”. ### Topics Covered - Introducing Ken Weary, COO of Hotjar (0:15) - Ken's path to becoming Hotjar's COO (1:37) - What the COO owns at Hotjar (5:14) - Navigating GDPR and global privacy regulation (6:21) - How the Contentsquare acquisition came about (9:19) - Negotiating two-way due diligence on the buyer (13:31) - Hotjar's just cause of inspiring change through empathy (14:46) - Running the business through grueling diligence (17:12) - Digital nomad life and slow travel routines (21:38) - Remote-first since 2014 and why hybrid fails (26:14) - Harry Potter houses and Culture Jar rituals (29:43) - Retention and the great reshuffling (33:10) - Advice for COOs joining a new company (35:59) - A Russian VAT letter and a $10,000 quote (38:52) ### Mentioned in This Episode - Ken Weary on LinkedIn - Contentsquare: Enterprise analytics company that acquired Hotjar - Simon Sinek: Inspiration for Hotjar's why and just cause - GitLab Handbook: Cited as the reference playbook for remote operations --- ## Steve Taylor on Lyft's Pink Mustaches & a $20B IPO URL: https://betweentwocoos.com/from-the-white-house-to-a-20b-ipo-hiptrain-coo-fmr-lyft-exec-steve-taylor-on-man/ Published: 2022-03-03 ### Summary In this episode, Michael Koenig speaks with Steve Taylor, Co-founder and COO at HipTrain, about scaling Lyft from roughly 200 employees to a $20 billion IPO and what it takes to build an online fitness marketplace. Steve traces his path from flying E-2C Hawkeyes in the Navy and coordinating continuity of operations at the White House through five years of consulting and angel investing to the COO seat. Steve recalls John Zimmer's refusal to fixate on Uber, splitting his weeks between D.C. and New York while leading a team of more than 200, and receiving a letter of intent from Assurant on his third day as Fixt's COO. He also explains the MAYA principle behind Lyft's pink mustaches and HipTrain's supply-first marketplace, where trainers in Latin America earn double local rates and US members pay about a tenth of typical personal training costs. ### Topics Covered - Introducing HipTrain co-founder and COO Steve Taylor (0:13) - From the Navy and White House to startups (1:03) - How military autonomy shaped his operating style (6:51) - Why Steve joined Lyft in 2015 (10:06) - Lyft's early hypothesis and John Zimmer on Uber (11:40) - Running New York and the Mid-Atlantic territories (13:38) - Fixt's acquisition by Assurant and due diligence (17:14) - The MAYA principle and digitizing analog experiences (21:34) - Launching HipTrain into pandemic driven demand (25:35) - Building marketplace supply with trainers in Latin America (27:09) - Global labor arbitrage as a competitive advantage (29:55) - A remote team spanning six countries (31:36) - A letter of intent on day three (32:25) ### Mentioned in This Episode - Steve Taylor on LinkedIn - Lyft: Where Steve ran major territories through the $20 billion IPO - Fixt: Baltimore startup where Steve was COO before its acquisition - Assurant: Fortune 300 insurer that acquired Fixt in 2020 - Big Health: Digital therapeutics company where Steve served as COO - Georgetown University: Grad school Steve attended while working at the White House - PwC: Steve spent four years here after it acquired PRTM - MAYA principle: Most advanced yet acceptable, the design concept Steve applied --- ## Joe Meyer, ExecThread CEO on Landing Hidden Exec Roles URL: https://betweentwocoos.com/execthread-ceo-joe-meyer-on-accessing-hidden-exec-retained-searches-how-to-land/ Published: 2022-02-23 ### Summary In this episode, Michael Koenig speaks with Joe Meyer, Founder and CEO at ExecThread, about the hidden job market of executive roles that never reach public job boards. Joe traces his path from two failed founding attempts through leadership at HopStop, acquired by Apple, and Quigo, acquired by AOL, to building a network that surfaces confidential retained searches. Joe explains how ExecThread began as a passion project while he worked at Apple, growing from a few dozen contacts into a vetted network of over 125,000 members. He details the reveal experience behind 95 percent of the platform's more than 3,000 retained searches, why HopStop competed with Google Maps at 15 employees, and why warm introductions outperform cold outreach to hiring managers. ### Topics Covered - Introducing Joe Meyer and ExecThread (0:14) - Joe's path from failed startups to CEO (1:35) - The hidden job market problem (3:39) - Grassroots beginnings while at Apple (5:05) - Marketplace dynamics and 125,000 members (7:15) - Hands-on leadership in flat small teams (9:44) - Hiring young talent and leading by example (11:30) - Transparency through startup potholes (14:00) - Staying motivated when failure looms (16:59) - Operating inside eBay, AOL, and Apple (19:11) - Leading teams through acquisitions (22:17) - A steady hand through unexpected challenges (26:19) - Advice for landing executive level roles (29:04) ### Mentioned in This Episode - Joe Meyer on LinkedIn - HopStop: Joe's prior startup, acquired by Apple - Quigo: Startup where Joe was an operator, acquired by AOL - eBay: Joe spent four years there as a general manager --- ## Nathaniel Manning, Kettle COO on Climate Risk Insurance URL: https://betweentwocoos.com/kettle-coo-white-house-innovation-nathaniel-manning-on-balancing-risk-in-a-chang/ Published: 2022-02-15 ### Summary Kettle COO, Nathaniel Manning, talks about balancing risk in a changing climate, structure without bureaucracy, evolution by design, good decision making, the social contract of insurance, and sitting on a monastery cushion for 3 months. He also talks about old guard vs new guard, building the plane while it's flying, making the implicit explicit, and evolution by design. Nathaniel has a long career of founding and leading companies including Fellow Robots, BRCK, the largest provider of public wifi in Africa, and Ushahidi the world’s largest open-source platform for crisis response. Along the way, he worked on furthering clean energy as part of the Clinton Climate Initiative at the Clinton Foundation, and Nathaniel was part of the Obama Administration's first class of Presidential Innovation Fellow where he was special advisor on open data at USAID, the world's premier international development agency, where he went on to become the Chief Data Officer. With that kind of track record, it’s safe to say that Nathaniel puts his money where his mouth is when it comes to creating technological solutions to some of the world’s biggest problems. ### Topics Covered - Introducing Nathaniel Manning and Kettle (0:18) - Drive shaped by three months in a Zen monastery (1:52) - Reinsurance as the safety net below the safety net (3:48) - Underwriting catastrophes with endowment and pension capital (10:23) - Predicting the 14 wildfires that cause most damage (14:15) - The COO as the executive team's puzzle piece (17:16) - A responsibilities doc with one name per decision (20:58) - Open sourcing the responsibilities templates (26:18) - High stakes as fuel rather than stress (27:48) - Founder market fit and the fertility insurance test (30:40) - Leading Ushahidi through a harassment crisis (36:28) - Acknowledgement and space while steering the team (41:12) - Skipping a meeting with President Obama for a honeymoon (43:47) ### Mentioned in This Episode - Nathaniel Manning on LinkedIn - Ushahidi: open source crisis response platform Nathaniel led as COO - BRCK: public wifi provider in Africa from Nathaniel's career - Primer: education startup founded by Ryan Delk, Kettle's first investor - Presidential Innovation Fellows: Obama era program where Nathaniel served in the first class - Old Guard, New Guard: blog post Nathaniel revisits on scaling startup teams - @natpmanning on X: where Nathaniel says listeners can follow him --- ## Dave Weiss, Hatch COO on Shark Tank & 2M IoT Devices URL: https://betweentwocoos.com/hatch-coo-dave-weiss-on-selling-2-million-iot-devices-cofounding-a-company-with/ Published: 2022-02-08 ### Summary Dave Weiss, co-founder, and COO of Hatch, joins us to discuss what it takes to confound a hardware company with his wife, sell 2 million IoT devices, the heightened consumer expectations of hardware, visit customers' homes, going from Shark Tank to VC fundraising, moving from CTO at BabyCenter to COO, and believing in wet paint. Prior to co-founding Hatch, Dave was the CTO of BabyCenter, where he was responsible for software engineering and product. ### Topics Covered - Introducing Dave Weiss and Hatch (0:00) - From engineer to CTO to COO (1:21) - Dividing COO responsibilities at Hatch (4:28) - Funding a first-time hardware startup (6:09) - Consumer expectations of hardware versus software (8:07) - Debugging devices in customers' homes (9:25) - From Shark Tank to venture fundraising (10:54) - Co-founding a company with his wife (13:50) - Leading 80 plus employees as married co-founders (16:04) - Keeping the team confident through transparency (17:42) - Screening hires for bias toward action (20:45) - Hatch company values including wet paint (22:05) - Building camaraderie on a remote team (25:03) - Advice on enjoying the scaling journey (28:36) ### Mentioned in This Episode - Dave Weiss on LinkedIn - BabyCenter: Where Dave was CTO before founding Hatch - True Ventures: Hatch's main backer, first investor in Ring and Peloton - Shark Tank: Hatch appeared on the ABC show in 2016 --- ## Valerie Hoecke, Dia&Co. COO on Growth to Survival Mode URL: https://betweentwocoos.com/valerie-hoecke-dia-co-coo-fmr-cdo-at-lvmh-on-how-a-50b-company-preps-you-for-any/ Published: 2022-02-01 ### Summary Dia&Co. COO and former LVMH Chief Digital Officer, Valerie Hoecke, joins to chat on how a $50B co. like LVMH preps you for anything, how Dia&Co. solves the shopping challenges faced by plus size women, the impact of size discrimination in the workforce, the challenges that "try before you buy" creates, and going from growth to survival mode and back again. Valerie kicked off her career in the early days of the internet with one software exit followed by one agency exit, in the Web 1.0 days. She gained a ton of experience across brand building and performance marketing, as well as e-commerce, in 15 years working in digital agencies in various roles including VP Operations, GM, VP Client Services. Most recently she served as the Global Chief Digital Officer for the world’s foremost luxury conglomerate, LVMH, across 16 beauty brands. LVMH Beauty brands include a mix of iconic centuries-old luxury household names such as Parfums Christian Dior, powerhouses like Benefit Cosmetics, Givenchy, and Fresh, as well as more recently incubated hot businesses such as Fenty Beauty. ### Topics Covered - Valerie's path from web developer to COO (1:37) - Agency years build pattern matching skills (6:11) - LVMH lessons in financial rigor and creativity (10:18) - Resetting everything from LVMH to startup life (12:56) - The COO mandate at Dia&Co (16:49) - Connecting plus size customers with inclusive brands (18:50) - Style boxes, customer empathy, and fit data (21:19) - Try before you buy and returns logistics (25:09) - From survival mode back to growth mode (27:36) - Keeping a remote first team connected (32:37) - Marketplace, wardrobing, and livestream commerce bets (36:55) - Testing the CEO and COO relationship (40:52) - An employee who fired themselves (44:05) - Size discrimination in the workforce (47:24) ### Mentioned in This Episode - Valerie Hoecke on LinkedIn - LVMH: Where Valerie was global chief digital officer for beauty - Benefit Cosmetics: LVMH brand where Valerie ran e-commerce before the CDO role - Madewell: Brand partnership bringing inclusive sizing to Dia&Co - Stitch Fix: Business model comparison for try before you buy --- ## Catherine Stewart on Scaling Ops at Shippo & Automattic URL: https://betweentwocoos.com/part-1-catherine-stewart-on-scaling-operations-and-people-management-at-shippo-a/ Published: 2022-01-19 ### Summary Catherine Stewart is the former Chief Operating Officer at Shippo and Chief Business Officer at Automattic (WordPress),  joins us in part one of a special two-parter, to talk about the craft of scaling operations at hyper-growth tech companies. Topics include shifting strategic priorities at Automattic to also focus on revenue generation and e-commerce through the acquisition of WooCommerce, the shift from Facebook to Automattic, balancing the entrepreneurial mindset with the need for processes, not sugar-coating it, and why her time at Random House yielded some of the most valuable learnings of her career. Part two, coming next month, focuses on scaling the go-to-market and creating $B's in value. Shippo is a shipping software company backed by Bessemer and D1, where she led Marketing, Sales, Business Development, Customer Success, Customer Support, People Ops, and Strategic Planning. During her time at the company, Shippo's revenue grew 3x faster than the US eCommerce shipping market, and the company's valuation grew from $220M to over $1B in just 18 months. ### Topics Covered - Introduction and Catherine's track record (0:08) - From McKinsey and publishing into tech (1:07) - Go-to-market passion over finance (3:24) - What drove Shippo's outsized growth (4:53) - First 30 days and the listening tour (6:17) - Change management and Automattic's monetization shift (10:35) - Regrettable versus non-regrettable attrition (14:54) - Hiring quality during hypergrowth (17:38) - Defining the COO role with the CEO (22:25) - Recycling playbooks and org structures (25:10) - Cherry-picking lessons from Random House and Facebook (27:15) - Mentor advice and the Audience Network launch (29:29) - Tiger teams balance innovation and process (34:24) - Advice for COOs joining a new company (39:26) --- ## Doug Hanna, Grafana Labs COO on GTM at $3B Scale (Pt 2) URL: https://betweentwocoos.com/part-2-grafana-labs-coo-doug-hanna-on-scaling-the-go-to-market-machine-of-a-3b-t/ Published: 2022-01-11 ### Summary Doug Hanna, COO at Grafana Labs, joins us to discuss scaling a company to $3B in valuation after raising $330M in funding. As a former Zendesk VP of Ops, Doug has had front seats at both companies, during hyper-growth. This episode, Part 2, focuses on scaling the go-to-market machine of a multi-billion dollar company. Grafana Labs is the company behind the lead open source observability platform, Grafana, used by the likes of Salesforce, Paypal, Verizon, Ebay, and 750K other instances. Part 1 of Doug's session dropped on January 4th, 2022 and focuses on Doug's path to COO and scaling people and culture. ### Topics Covered - Introduction and why Doug returns for part two (0:17) - Joining pre-Series A Grafana at 70 people (1:32) - Growth drivers: open source funnel and macro tailwinds (3:54) - Observability explained and the open source business model (6:43) - Financial services traction and ideal customer profile (10:39) - Structuring the sales organization by region and segment (13:04) - Breaking out US federal and exploring verticals (14:37) - The adopt, land, expand customer journey (16:54) - Growth stages from product market fit to repeatability (20:01) - Hiring 500 people while running the business (25:20) - OKRs, meeting cadence, and the operating system (28:27) - Where Grafana Labs goes from here (31:38) - Advice to his 2019 self on hiring (33:24) - Celebrating milestone deals remotely during COVID (37:31) ### Mentioned in This Episode - Doug Hanna on LinkedIn - Zendesk: Doug's prior company where he was VP of Operations - Prometheus: Ecosystem project Grafana Labs runs as a managed service - JP Morgan: Named Grafana Labs a top vendor, a financial services proof point - WordPress: Business model comparison for monetizing open source - AppDynamics: Doug's favorite story, acquired the day before its IPO --- ## Doug Hanna, Grafana Labs COO on Open Source at $3B (Pt 1) URL: https://betweentwocoos.com/part-1-grafana-labs-coo-doug-hanna-on-building-a-3b-company-with-open-source-sca/ Published: 2022-01-04 ### Summary Doug Hanna, COO at Grafana Labs, joins us to discuss scaling a company to $3B in valuation after raising $330M in funding. As a former Zendesk VP of Ops, Doug has had front seats at both companies, during hyper-growth. This episode, Part 1, focuses on people and culture: what goes into scaling from 70 to 400 net new employees in a mere 18 months. Grafana Labs is the company behind the lead open source observability platform, Grafana, used by the likes of Salesforce, Paypal, Verizon, Ebay, and 750K other instances. Part 2 of Doug's episode will air in a few weeks and focuses on scaling the go-to-market. ### Topics Covered - Doug's path from tech support to COO (1:24) - Evaluating Grafana through tech, TAM, and team (3:35) - Open source as a go-to-market model (5:38) - COO scope and the CRO comparison (7:04) - Growth beyond expectations in 24 months (10:03) - Hiring 400 people without diluting culture (11:29) - Building community across a distributed team (13:59) - Async communication and its limits (16:06) - Advice on dealing with what you avoid (18:27) ### Mentioned in This Episode - Doug Hanna on LinkedIn - Zendesk: Where Doug spent four years as VP of Operations - Automattic: Doug's early employer, where he and Michael first met - Help.com: Customer service startup Doug founded and ran for 18 months - A Small Orange: Web hosting company Doug ran for four years and sold - MongoDB: Cited as a comparable open core business model - Elastic: Cited alongside MongoDB as a similar open source business - GitLab: Referenced for its async first distributed work culture --- ## Micah Rosenbloom on COO to VC at Founder Collective URL: https://betweentwocoos.com/micah-rosenbloom-founder-collective-managing-partner-former-brontes-coo-on-build/ Published: 2021-12-20 ### Summary Before Micah Rosenbloom was a venture capitalist, he was the co-founder and COO of Brontes Technologies, which he sold to 3M. Micah and his business partner Eric then went on to found the VC firm, Founder Collective, which has made investments in companies like Uber, ThreadUp, Hotels Tonight, Venmo, PillPack, and more. Micah joins us to discuss deciding who's CEO and COO, not shying away from tough conversations, hiring the right people, founding a VC firm and introducing ops to it, going through a transaction to a major corporation, the downside of making investments via Zoom, and how to identify investors that have true conviction in your company. Eric Paley: https://twitter.com/epaley/Raj De Datta: https://twitter.com/rdedattaScott Belsky: https://twitter.com/scottbelskyBill Tranchard: https://twitter.com/btrenchardChris Dixon: https://twitter.com/cdixonJames Tamplin: https://twitter.com/jamestamplinDave Frankel: https://twitter.com/dafrankel ### Topics Covered - Introducing Micah Rosenbloom and Founder Collective (0:08) - Founding Brontes and dividing the CEO and COO roles (1:44) - Having the hard conversation about roles early (7:22) - COO as culture carrier and lead recruiter (10:31) - Becoming a VC and founding Founder Collective (14:58) - Introducing operations and OKRs at Founder Collective (19:35) - Looking for yin and yang in founding teams (23:25) - COOs as an early stage asset (25:42) - Going through the 3M transaction as COO (27:35) - Keeping trains running during the deal (30:26) - Staying frugal when resources get big (33:26) - Zoom investing versus visiting founders in person (35:56) - Never thought I'd see that moments (38:09) - Confusing investor speed with conviction (40:49) ### Mentioned in This Episode - Micah Rosenbloom on LinkedIn - Brontes Technologies: Dental 3D scanning startup Micah cofounded and sold to 3M - 3M: Acquired Brontes in 2006 and Micah became general manager - Invisalign: Early connection that focused Brontes on digital dental impressions - Andreessen Horowitz: Credited with investing in operational support for founders --- ## Marie Prokopets, Nira COO on Pivoting Search to Security URL: https://betweentwocoos.com/nira-coo-marie-prokopets-on-pivoting-from-search-to-security-context-switching-b/ Published: 2021-12-14 ### Summary After doing $26B of M&A at Diageo, Marie Prokopets joined the startup world, and together with Hiten Shah, founded Nira.com a way to secure your company documents and access controls. As COO at Nira, Marie joins us to talk about pivoting from search to security, context switching, and what happens when vendors mess up access controls. ### Topics Covered - Introduction to Marie Prokopets and Nira (0:08) - Career path from PwC and Diageo to startups (0:46) - Why the COO role was the natural fit (4:14) - What surprised Marie about the COO role (6:12) - Bringing operational rigor to go-to-market (8:43) - A vendor access control horror story (12:04) - Pivoting from FYI enterprise search to security (14:39) - Why stale document access stays hidden (18:30) - 32% can still access former employer documents (19:53) - Advice for new COOs on learning mindset (20:38) - Context switching tips and organized notes (22:32) - Where to find Nira and Marie (24:05) ### Mentioned in This Episode - Marie Prokopets on LinkedIn - Nira: Marie's document access security company for IT teams - FYI: Enterprise search product Marie and Hiten pivoted into Nira - Diageo: Where Marie did M&A, strategy, and product innovation - PwC: Marie's start in marketing then strategy and M&A consulting - Google Workspace: First platform Nira secures for document access control --- ## Justin Reilly, Tucows CPO on Product Design & Operations URL: https://betweentwocoos.com/tucows-chief-product-officer-justin-reilly-on-how-product-design-influences-oper/ Published: 2021-12-06 ### Summary Tucows Chief Product Officer, Justin Reilly, joins as our first non-COO, and shares on your customer's best last experience, how product design influences operations and where AI fits, Ting's excellent customer care, and how photos almost pushed a launch. Justin focuses on building the next generation of consumer products, particularly where AI meets customer experience. Prior to Tucows, Justin was Head of Product & CX Innovation at Verizon. He founded Focus Health, Grey Seven Labs, and Qstir. He was a Director of Strategy and Experience at Macquarium, lead the Strategy and Innovation team at Arke Systems. He currently advises a number of startups focused on the next generation of AI platforms and products. ### Topics Covered - Introducing Justin Reilly, the first non-COO guest (0:00) - From college basketball to Tucows chief product officer (1:22) - Moving from healthcare to telecom (4:47) - Product's expanding reach into back office operations (6:30) - Competing against the customer's last best experience (9:12) - Not everything needs a conversational interface (11:20) - Investing in human customer care at Ting (13:13) - Why Tucows does not have a COO (16:14) - Where AI fits in business operations (18:30) - Hire the smartest people, get out of their way (22:01) - Building trust in remote first teams (25:28) - Picture day saves a product launch (29:30) - Advice for COOs partnering with a CPO (32:17) ### Mentioned in This Episode - Justin Reilly on LinkedIn - Focus Health: Health startup Justin founded to tackle chronic illness - DISH: Took over Ting's mobile business in August 2020 - David Sontag: MIT researcher on Focus Health's longitudinal health work --- ## Jim Stewart, True Ventures COO on Taking 4 Companies Public URL: https://betweentwocoos.com/true-ventures-coo-jim-stewart-on-taking-four-companies-public-venture-capital-fi/ Published: 2021-11-29 ### Summary True Ventures Chief Operating Officer, Jim Stewart, on what it's like to take four companies public, what goes into the operations to run a venture capital firm, how to take calculated risks, and what to do when you realize that you've just violated US government export controls when you're doing an IPO roadshow (don't panic). True Ventures is a venture capital firm with an astonishing track record of investing in the best companies like Peleton, Fitbit, Ring, Duo Security, Automattic, and Sweetgreen, which just went public on the New York Stock Exchange. Jim initially joined True Ventures as CFO in 2012 and now leads all operations as the firm's COO. He brings substantial operational and financial experience to venture-backed tech and biotech companies. Jim has held numerous operating and CFO positions, leading four companies through their IPO processes. When he is not focused on operations, he's doing all sorts of high-octane activities like racing his Yamaha R6 motorcycle. ### Topics Covered - Introduction and Jim Stewart's background (0:00) - Racing motorcycles and calculated risk (1:17) - From CFO to COO at True Ventures (1:51) - What a COO does at a venture firm (2:54) - Board cadence and founder communication (4:04) - Back office operations, audits, and valuations (5:23) - Pattern recognition in successful portfolio companies (8:43) - The CEO and COO partnership (10:33) - Adapting the C-suite as companies scale (12:43) - Pre-IPO surprises and catch-up work (14:28) - Export control violation on an IPO roadshow (16:09) - Resolving the export issue with regulators (18:56) - Leading with transparency and calm (21:00) - First 90 days advice for new COOs (22:37) ### Mentioned in This Episode - Jim Stewart on LinkedIn - True Ventures: The venture firm where Jim leads operations - PR1 Motorsports: Pro race team Jim crews with - U.S. Department of Commerce: Regulator in the export control disclosure story --- ## Allie Fleder, SimplyWise COO on Early-Stage COO Roles URL: https://betweentwocoos.com/allie-fleder-coo-at-simplywise-on-changing-industries-how-coo-roles-vary-remote/ Published: 2021-11-21 ### Summary In this episode, Michael Koenig speaks with Allie Fleder, COO at SimplyWise, about changing industries from travel to fintech, how the COO role varies at an early-stage startup, and leading a team that became distributed during the pandemic. Fleder describes her route through Latin American poetry, political speechwriting, and a chief of staff post, then negotiating a catch-all role covering accounting, HR, recruiting, legal, customer support, and product. Fleder explains why her responsibilities shift every three to four weeks, from Googling what SEO is in her first month to handling the customer support that now takes 80 percent of her time. She recounts cold-messaging 20 COOs on LinkedIn and hearing back from two, the luggage delivery that ended in an emergency room, and why new COOs should pick a CEO they trust and use existing templates instead of reinventing them. ### Topics Covered - Cold open and introduction (0:00) - From poetry and speechwriting to two-time COO (1:24) - Negotiating a catch-all COO role at SimplyWise (2:32) - A role that shifts every three to four weeks (4:37) - Talking to users as a product constant (6:23) - Writing the company mission as an anchor (8:41) - Deciding when to hand off customer support (10:29) - Distributed team and deliberate remote work choices (12:24) - Over-communicating through pivots and uncertainty (14:17) - Keeping leadership debates behind closed doors (16:00) - The bleeding head luggage delivery story (18:31) - Advice for new COOs on CEO fit and peers (22:03) - Use existing templates instead of reinventing them (24:38) - Knowing your people and what motivates them (26:06) --- ## Rich Wallach, Deepak Chopra Global COO on Uncertainty URL: https://betweentwocoos.com/deepak-chopra-global-coo-rich-wallach-on-synchrodestiny-managing-through-uncerta/ Published: 2021-11-21 ### Summary In this episode, Michael Koenig speaks with Rich Wallach, COO and CFO at Chopra Global, the company behind Deepak Chopra's wellness work, about creating safety and certainty for employees while managing constant uncertainty. Wallach traces a path from philosophy major at the University of Michigan through a decade at Credit Suisse and a streaming discovery startup to a role he describes as coming home, or synchrodestiny. Wallach explains why radical transparency can backfire, why 95 percent of competitor news never goes anywhere, and how Chopra Global went fully remote, dropping from 80 employees in California to 28 with staff now spread across 17 states. He covers Monday all-team calls that open with a 20-minute meditation, an app that reached 700,000 installs without paid marketing, and advice for COOs entering a new company: set expectations with the CEO first. ### Topics Covered - Introduction and Michigan football banter (0:00) - From philosophy major to investment banking (1:06) - Building and selling a streaming discovery startup (4:37) - Coming home to Chopra Global (6:33) - Creating safety and security for employees (8:20) - Owning strategy and keeping the company focused (12:05) - Balancing transparency without creating uncertainty (13:29) - Treating employees as human beings first (16:32) - How processes give people certainty (19:53) - Staying connected as a fully remote company (20:54) - Going office-free and hiring across 17 states (22:00) - Banking war stories and unexpected problems (25:56) - Advice for COOs entering a new company (31:14) - Lemurs and the new Chopra app (37:07) ### Mentioned in This Episode - Rich Wallach on LinkedIn - Credit Suisse: Where Wallach spent a decade and first became COO - GoWatchIt: Streaming search startup Wallach co-founded and sold - Automattic: Michael's example of a fully distributed company - University of Michigan: Wallach's alma mater, philosophy and pre-med --- ## Introducing Between Two COO's URL: https://betweentwocoos.com/introducing-between-two-coos/ Published: 2021-11-18 ### Summary In this episode, Michael Koenig introduces Between Two COO's, a podcast where a different COO joins each episode to share stories and advice. He traces the show's origin to his promotion to his first COO role, when he reached out to friends, mentors, and advisors, then connected with other COOs who had done the job before. A recurring idea from those conversations, that the advice should be open sourced, became the show. --- ## Blog Posts ### Allie Fleder on the COO Role at an Early-Stage Startup URL: https://betweentwocoos.com/blog/what-does-a-coo-do-early-stage-startup-allie-fleder/