The Operator's Library

Frameworks and field notes from the podcast, optimized for operators who'd rather read than listen.

Each conversation on Between Two COO's runs 45 to 90 minutes. The articles here distill the most useful frameworks our guests have shared into 5 to 15 minute reads. If you don't have time to scrub a podcast feed for the one operating lesson you actually need this week, start here.

Tom Masterson, COO of Deep Genomics, on the Between Two COOs podcast.
Latest

Lab in the loop: teaching an AI what toxic looks like

Anybody can build a lab in the loop. Deep Genomics COO Tom Masterson says the advantage is in what you feed it: data designed for machine learning, including test molecules that are intentionally toxic so the model learns what toxic looks like.

3 min read Read it →

More recent

AI token cost keeps falling. The debt behind it does not.

AI token cost is falling 60 to 80 percent a year. That is good news for anyone buying tokens and a serious problem for anyone who borrowed to make them. Paul Kedrosky of SK Ventures explains the math, and what operators should take from it.

4 min read

What a forward-deployed team finds inside a mortgage company

Moburst sent a team on-site to a mortgage company to find where AI could help. What they found was forms checked by hand, blurry phone photos, and weekend calls with no context. The first fixes were not AI, and the rule that came out of it applies to any operator.

5 min read

Seven agencies and a calendar: what actually decides whether a data center in orbit gets built

An orbital data center is not a launch, not a communications satellite, not an imaging satellite, so seven agencies each own a slice of it and the FDA is one of them. Cowboy Space COO Joe Yaffe on the unglamorous constraints that actually decide whether this gets built.

9 min read

The physics is the easy part: Joe Yaffe of Cowboy Space on what it actually takes to put a data center in orbit

Joe Yaffe spent 31 years as a Silicon Valley lawyer before becoming COO of Cowboy Space. He argues an orbital data center needs no new science, only execution, and that the decision which closes the economics is letting the rocket double as the radiator.

11 min read

AC vs DC power: the 1890s design decision that could become the next bottleneck in AI

AC vs DC power, explained: why every conversion between the grid and an AI chip burns energy as heat, and why that path is now worth rebuilding.

7 min read

Jevons paradox and the AI infrastructure bet: the 160 year old idea behind hundreds of billions in spending

An 1865 observation about coal is the argument underneath hundreds of billions in AI infrastructure spending. Jevons paradox, and what would break it.

6 min read

Generative engine optimization for physical products: Riikka Söderlund of Katana on why AI search cannot see what you cannot count

Katana COO Riikka Söderlund on generative engine optimization, why AI search hides out-of-stock products, and the brand selling at a loss unaware.

8 min read

AI agent security after a model walked out of its own sandbox: what operators should actually do

A model escaped its test environment and attacked another company. The AI agent security failures were operational, and seven of them are yours to fix.

6 min read

The full library

Every episode, most recent first.

Post acquisition integration and the day one speech that turned Grindr around: Rick Marini on knowing which seat you are best in Rick Marini on post acquisition integration at Grindr, the day one speech that reset a broken culture, and why he would rather be a great COO. 7 min read Workflow automation, fourteen years in, and the code red that reset everything: Wade Foster of Zapier Zapier CEO Wade Foster on workflow automation in the AI era, the code red he called after GPT-4, and giving revenue back to compound over a decade. 8 min read Making the OKR framework the actual operating system: Zulema Quintáns of Noda on focus, flexibility and wasted energy Noda COO Zulema Quintáns on making the OKR framework stick, why 70 percent is the target, and the question that killed a warehouse full of sensors. 7 min read Corporate innovation with one investor instead of a hundred: Peter Rojas of Mozilla Mozilla's Peter Rojas on corporate innovation, why building inside a company means one investor instead of a hundred, and speed of market discovery. 12 min read Allie Fleder on the COO Role at an Early-Stage Startup What does a COO do at a startup? Allie Fleder, COO of SimplyWise, on how the role varies, the CEO partnership, and creating clarity in ambiguity. 8 min read Identity and access management for AI agents, and the synthetic identities nobody is governing: Greg Keller of JumpCloud JumpCloud CTO Greg Keller on identity and access management, the synthetic identities agents create, and why AI is a practical insider threat. 8 min read Stakeholder capitalism, values versus politics, and why Friedman stopped working: Seth Levine on Capital Evolution Foundry's Seth Levine on stakeholder capitalism, the difference between values and politics for a CEO, and why shareholder primacy stopped working. 7 min read How to find a mentor, and how to be one: Brad Feld on give first and telling stories instead of should Brad Feld on how to find a mentor and be one, why telling a story beats saying should, and the difference between a coach and a therapist. 11 min read Payment orchestration, open payments, and whether the rails are ready for agents: Peter Dougherty of Spreedly Spreedly president Peter Dougherty on payment orchestration, why the category is becoming open payments, and whether the rails can handle AI agents. 7 min read Customer onboarding, the three Ps of a meeting, and coaching with a rubric: Harris Clarke of GuideCX GuideCX COO Harris Clarke on customer onboarding as a tracked experience, the three Ps that fix a meeting agenda, and coaching with an AI rubric. 10 min read The strategic planning process, and the working rhythm underneath it: Anna Elwood of Cascade Cascade COO Anna Elwood on the strategic planning process, the working rhythm that makes it executable, and the five pillars of strategic maturity. 7 min read Software quality metrics at the scale of 45% of the web: Lance Willett of Automattic Automattic Chief Quality Officer Lance Willett on software quality metrics, benchmarking technical work the way finance benchmarks revenue. 7 min read Answer engine optimization, and designing a site for humans and agents at once: Linda Tong of Webflow Webflow CEO Linda Tong on answer engine optimization, why sites may need a human version and an agent version, and owning the full code lifecycle. 7 min read AI in customer service, and the tradeoff nobody says out loud: Doug Hanna of Kustomer Kustomer president Doug Hanna on AI in customer service, why specialized agents beat one general bot, and the cost versus satisfaction tradeoff. 7 min read Sales and marketing alignment, and why RevOps is always hired too late: Brad Rosen of Sales Assembly Sales Assembly president Brad Rosen on sales and marketing alignment, the RevOps hiring ratio nobody hits, and why the spreadsheet is just a sheet. 12 min read Change management when you have to disrupt yourself: Aydin Mirzaee on pivoting Fellow to AI Fellow CEO Aydin Mirzaee on change management during an AI pivot, retiring a company value to unblock it, and why most decisions are reversible anyway. 7 min read AI governance when you have no bandwidth for it: Flick Fisher on the EU AI Act now in force Privacy partner Flick Fisher on practical AI governance, the prohibited practices now in force, and the hygiene steps that matter more than a framework. 10 min read Building a procurement process that people actually follow: Justin Etkin of Tropic Tropic COO Justin Etkin on building a procurement process people actually follow, the visibility and controls that come first, and where AI fits. 12 min read The hidden job market for C-suite roles, and what actually gets you shortlisted: Evan Grossman of True Search True Search partner Evan Grossman on the hidden job market for C-suite roles, why searches exist at all, and the self-awareness that gets you shortlisted. 12 min read Strategy vs tactics as bets on different time horizons, and pricing risk in money and time: Jon Mark of Vestwell Vestwell COO Jon Mark on strategy vs tactics as bets on different time horizons, pricing every risk in money and time, and one anchor metric. 13 min read What a SPAC actually is, and why it was not the shortcut: Valentin Gruber of HomeToGo HomeToGo COO Valentin Gruber on what a SPAC actually is, why 80% of the work is the same as an IPO, and buying only profitable companies. 13 min read The master franchise model, and why maybe they're right changed everything: Stacey Ryan of School of Rock School of Rock COO Stacey Ryan on the master franchise model overseas, running one voice across company and franchise schools, and reorganizing for growth. 14 min read The one on one meeting as a process, weekly meeting limits, and the seven attendee ceiling: Aydin Mirzaee of Fellow Fellow CEO Aydin Mirzaee on what a one on one meeting is really for, weekly meeting hour limits by role, and the seven attendee decision ceiling. 13 min read Delegation in leadership, unique ability, and hiring accountable people: Cameron Herold returns Cameron Herold on delegation in leadership, the unique ability filter, why he hires accountable people instead of holding people accountable. 13 min read The EU AI Act, read the week it leaked: Flick Fisher on risk tiers, providers, and the compliance clock Privacy partner Flick Fisher on the EU AI Act: the four risk tiers, who is a provider versus a deployer, the compliance clock, and the fines. 10 min read The ideal customer profile dartboard, and an enterprise readiness scorecard nobody wrote from the top: Greg Strickland of Productboard Productboard COO Greg Strickland on the ideal customer profile dartboard, moving upmarket with an enterprise readiness scorecard, and pod zero. 15 min read Global network effects, and the core values exercise that finally worked: Tao Tao of GetYourGuide GetYourGuide co-founder Tao Tao on global network effects, the core values exercise that finally worked, and going to zero revenue in 2020. 16 min read The hiring process steps behind near-zero attrition, and why remote is its own function: Allan Christensen of Doist Doist COO Allan Christensen on the hiring process steps behind near-zero attrition, why remote is its own function, and async by default. 12 min read Psychological safety without losing accountability, and the reference question that gets the truth: Dan Siroker of Rewind Rewind CEO Dan Siroker on psychological safety without losing accountability, the reference check question that gets honest answers, and AI leverage. 17 min read Community solar, five acquisitions, and disrupting a regulated monopoly: Kate Henningsen of Arcadia Arcadia co-founder Kate Henningsen on how community solar works, buying five companies in three years, and running a board with five set meetings. 16 min read Asynchronous communication, and why remote work is an operating model: Darren Murph Darren Murph on asynchronous communication, why remote work is an operating model and not a perk, and the no agenda no attend meeting rule. 15 min read OKR vs KPI, a 72 hour hackathon, and a psychologist on staff: Nitin Gupta of Prisma Prisma COO Nitin Gupta on OKR vs KPI, running a 72 hour internal hackathon, and why the company keeps a trained psychologist on staff. 13 min read Running a public benefit corporation, and integrating 25 acquisitions: Shanaz Hemmati of ZenBusiness ZenBusiness COO Shanaz Hemmati on running a public benefit corporation, the CIO to COO move, and integrating 25 acquisitions at HomeAway. 10 min read SaaS spend management, and the two ways you are overpaying: Munish Gandhi of Productiv Productiv co-founder Munish Gandhi on SaaS spend management, the two kinds of underutilization, and controlling compliance at the point of purchase. 12 min read Solving the cold start problem in a two sided marketplace: Allen Narcisse of Gigs Gigs CEO Allen Narcisse on the cold start problem in a two sided marketplace, why he wants to make only 5% of decisions, and doing versus leading. 13 min read What is vertical farming? Tobias Peggs of Square Roots explains Square Roots CEO Tobias Peggs on what is vertical farming, replicating Genoa's climate for basil, and a product roadmap ordered lightest to heaviest. 10 min read What is a B Corp, and what it costs to actually mean it: Stephan Jacob of Cotopaxi Cotopaxi co-founder Stephan Jacob on what is a B Corp versus a benefit corporation, turning factory scrap into product, and llamas on the balance sheet. 13 min read A strategy execution framework that launched 24 cities in a day: Woody Hartman of Lime Lime COO Woody Hartman on a strategy execution framework that launched 24 cities in a day, why cities became the customer, and when to step away. 14 min read Data controller vs processor, and why it decides your GDPR workload: Flick Fisher of Fieldfisher Fieldfisher partner Flick Fisher on data controller vs processor, what invalidating Privacy Shield changed, and GDPR compliance for US companies. 12 min read Cut a day to learn how to run effective meetings: Holger Seim of Blinkist Blinkist CEO Holger Seim on a four day week as the forcing function for how to run effective meetings, and the audio pivot that changed the company. 12 min read An operational plan example the size of a World Cup: Diego Camberos of Vodafone Qatar Vodafone Qatar COO Diego Camberos on an operational plan example built for the World Cup, radical simplification, and turning a buzzword into one KPI. 11 min read Franchise operations, from a Post-it note to 330 cities: Cameron Herold COO Alliance founder Cameron Herold on franchise operations that scale, the Post-it note test for any system, and why the leader should speak last. 13 min read Treat people like volunteers: strategy implementation steps from Cathy Hawley of Bolster Bolster co-founder Cathy Hawley on strategy implementation steps for a new people leader, treating employees like volunteers, and designing levels well. 13 min read The CEO and COO difference at a social impact company: Dale Pfeifer of Goodworld Goodworld CEO Dale Pfeifer on the CEO and COO difference in a founding pair, why corporate giving became a retention lever, and how to pitch investors. 9 min read A working CEO and COO definition: Jenny Lawton of Bolster Bolster EVP Jenny Lawton on a practical CEO and COO definition, the simplest operating system that works, and what MakerBot taught her about values. 11 min read A strategy implementation example from a three-sided marketplace: Jonathan Stull of Handshake Handshake COO Jonathan Stull on a strategy implementation example built on public commitments, solving a three-sided marketplace, and going global. 14 min read Operational excellence foundations differ by industry: Cyrus Mistry of GoGuardian GoGuardian COO Cyrus Mistry on how operational excellence foundations differ across software, airlines and theme parks, and why most of the job is people. 9 min read Rewriting the revenue operations job description: Art Harding of People.ai People.ai COO Art Harding on a revenue operations job description built on efficiency, effectiveness and transformation, not taking orders. 12 min read B Corp certification and executing the plan: Angela Tucci of Uplight Uplight COO Angela Tucci on B Corp certification, merging six companies during lockdown, and the spreadsheet she used to vet her next job. 13 min read A remote-first operational excellence strategy: Ken Weary of Hotjar Hotjar COO Ken Weary on a remote-first operational excellence strategy, running due diligence on your own acquirer, and building culture on purpose. 11 min read How to scale a service business across borders: Steve Taylor of HipTrain HipTrain co-founder Steve Taylor on how to scale a service business by building supply first, the MAYA principle at Lyft, and an acquisition on day three. 10 min read How to become a COO when the best jobs are never posted: Joe Meyer of ExecThread ExecThread CEO Joe Meyer on how to become a COO when executive roles never get posted, why warm introductions still win, and running a team of twelve. 10 min read Strategy execution starts with naming who decides: Nathaniel Manning of Kettle Kettle co-founder Nathaniel Manning on strategy execution through a doc naming one owner for every decision, and leading a team through a public crisis. 12 min read The CEO and COO relationship when you are married to the CEO: Dave Weiss of Hatch Hatch co-founder Dave Weiss on the CEO and COO relationship when the CEO is your wife, what hardware taught him, and values that actually shape hiring. 11 min read Operational excellence from LVMH to a startup: Valerie Hoecke of Dia&Co Dia&Co COO Valerie Hoecke on operational excellence learned at LVMH, running returns as a competitive advantage, and moving a team out of survival mode. 13 min read Chief operating officer duties are set by the CEO: Catherine Stewart of Shippo Former Shippo COO Catherine Stewart on how chief operating officer duties are set by the CEO, her 50 interview listening tour, and measuring attrition. 11 min read What is revenue operations at a hypergrowth company? Doug Hanna of Grafana Labs, part 2 Grafana Labs COO Doug Hanna on what is revenue operations in practice, segmenting a sales org by region and size, and reaching predictable pipeline. 11 min read How to scale a company from 70 to 500 people: Doug Hanna of Grafana Labs, part 1 Grafana Labs COO Doug Hanna on how to scale a company from 70 to 500 people, hiring that compounds, and why it feels like a new company every six months. 9 min read CEO vs COO: the conversation most founders postpone. Micah Rosenbloom of Founder Collective Founder Collective's Micah Rosenbloom on CEO vs COO, why he took a weekend to accept the second seat, and the founder conversation most teams postpone. 10 min read COO role responsibilities at a startup: Marie Prokopets of Nira Nira co-founder Marie Prokopets on COO role responsibilities at a startup, why go-to-market landed on her desk, and learning to context switch. 8 min read Where AI operations management actually helps: Justin Reilly of Tucows Tucows CPO Justin Reilly on where AI operations management actually helps, and why bad customer experience starts as a bad business decision. 10 min read What does a COO do at a venture capital firm? Jim Stewart of True Ventures What does a COO do at a venture capital firm? True Ventures COO Jim Stewart on fund operations, four IPOs, and a 90 day rule for new operators. 8 min read Rich Wallach, Chopra Global COO, on why every COO role description is different Chopra Global COO and CFO Rich Wallach on why no two COO role descriptions match, how to set expectations with a CEO, and running a fully remote company. 9 min read

Why a written library

The COO role is the most situational job in business. There's no formal training path, no standard job description, and very few playbooks that survive contact with a real company. Most of what works is learned from other operators who've been through it.

Between Two COO's exists to compress that learning curve. The podcast captures the full conversation with operators from companies like Google, LVMH, GitLab, Webflow, Tucows, Automattic, and Techstars. The articles in this library pull the frameworks and decisions worth saving into short, scannable, search-friendly form.

If you're new to operations or new to a Second-in-Command seat, browse the library above. If you're a returning reader, the newsletter below sends the next article to your inbox every Tuesday.

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