Guests

Every operator who's been Between Two COOs.

The people on this list run the day to day at companies you already know. Chief operating officers, presidents, chiefs of staff, and founders who took the operating seat, from seed stage through IPO and past it.

Every conversation is one guest and 45 to 90 minutes, which is long enough to get past the polished version. They talk about what actually happened: the hire made too late, the process that broke at 200 people, the strategy that was right on paper and impossible to execute, the quarter that missed and what they changed afterward.

Use the filter below to search by name, role, or company. If you are trying to solve something specific, it is usually faster to find the operator who has already solved it than to start from a framework. Each profile links to their full episode, and to the written version in The Operator's Library if you would rather read than listen.

• 

  Allan Christensen

  COO at Doist, the fully remote SaaS company behind Todoist and Twist. Focused on remote operations, hiring rigor, and building durable async culture at a globally distributed team.

• 

  Allen Narcisse

  Founder and CEO of Gigs, a hourly jobs marketplace for blue-collar workers. Former COO at Workrise, with earlier marketplace operating roles at Uber Eats and Lyft.

• 

  Allie Fleder

  Co-founder and COO at SimplyWise, an NYC-based fintech focused on financial document organization. Generalist operator with a background in policy, speechwriting, and travel startups.

• 

  Angela Tucci

  COO at Uplight, the clean energy software company built from the M&A of six companies and serving utilities and their consumers. Twenty-five-year veteran of enterprise software operations.

• 

  Anna Elwood

  COO at Cascade, the strategy-execution platform helping companies turn plans into results. Earlier ran operations at Zocdoc through its high-growth years in healthcare technology.

• 

  Art Harding

  COO at People.ai, the revenue operations and AI platform for enterprise sales teams. Operating focus on E2T, efficiency, effectiveness, and transformation, and on coaching as a leadership discipline.

• 

  Aydin Mirzaee

  Founder and CEO of Fellow, the AI meeting assistant. Previously co-founded Fluidware, the survey software company acquired by SurveyMonkey. Two-time Between Two COOs guest on meetings, AI, and company transformation.

• 

  Brad Feld

  Co-founder of Techstars and Foundry Group, longtime venture investor, and author of Give First. Boulder-based operator, writer, and mentor on startup communities and founder leadership.

• 

  Brad Rosen

  President at Sales Assembly, the professional development platform for B2B SaaS go-to-market teams. Previously ran revenue operations and partnerships at G2 through its scale-up years.

• 

  Cameron Herold

  Founder of COO Alliance and former COO of 1-800-GOT-JUNK. Author of five books including The Second in Command. Two-time Between Two COOs guest on the CEO/COO relationship and hiring A players.

• 

  Catherine Stewart

  Former COO at Shippo and former Chief Business Officer at Automattic. Ex-McKinsey and Facebook generalist who scaled go-to-market and operations across hyper-growth tech companies.

• 

  Cathy Hawley

  Former Chief People Officer of Return Path and co-founder of Bolster. People operations leader focused on intentional remote culture and treating knowledge workers as humans.

• 

  Cyrus Mistry

  COO at GoGuardian. Spent 14 years at Google as Director of Product Management for Chromebooks, bringing the platform into schools before moving into edtech operations.

• 

  Dale Pfeifer

  CEO and co-founder of Goodworld, a corporate social responsibility platform. Works with companies on CSR programs, employee engagement, and ESG strategy at scale.

• 

  Dan Siroker

  Co-founder and CEO of Rewind, the personalized AI built on everything you've seen, said, or heard. Former CEO and co-founder of Optimizely, the A/B testing platform.

• 

  Darren Murph

  Former VP of Remote at GitLab, called the Oracle of Remote Work by CNBC. Writes and advises on remote operations, low context communication, and async-first culture.

• 

  Dave Weiss

  Co-founder and COO of Hatch, the smart sleep device company. Sold over 2 million IoT devices, raised venture capital after Shark Tank, and previously CTO at BabyCenter.

• 

  Diego Camberos

  COO of Vodafone Qatar. Former CEO at Tigo Millicom in Senegal and Rwanda. Telecoms operator with deep experience navigating cultural and regulatory differences across markets.

• 

  Doug Hanna

  President and COO at Kustomer. Formerly Grafana Labs COO. Three-time Between Two COOs guest on open-source scaling, GTM strategy, and agentic AI in modern operations.

• 

  Evan Grossman

  Partner and Managing Director at True Search, leading the CEO and board practice at one of the largest executive recruiting firms in tech.

• 

  Flick Fisher

  Partner in the Technology and Data Group at Fieldfisher. Privacy and AI regulation specialist advising US companies on GDPR and the EU AI Act.

• 

  Greg Keller

  Co-founder and CTO at JumpCloud. Focused on identity access management, device security, and the governance challenges introduced by AI agents.

• 

  Greg Strickland

  COO at Productboard at the time of recording, focused on scaling from SMB to enterprise across product, sales, and cross-functional operations.

• 

  Harris Clarke

  COO at GuideCX. Former U.S. Department of State operator in the Office of the Chief of Protocol. Focused on trust, calm leadership, and systems that hold under pressure.

• 

  Holger Seim

  Co-founder and CEO at Blinkist. Grew the microlearning platform to 21 million users from Berlin and ran the company on a four-day workweek.

• 

  Jenny Lawton

  EVP at Bolster. Former CEO of Makerbot, COO of LittleBits, and President and COO at Techstars. Operator across hardware, consumer, and venture.

• 

  Jim Stewart

  COO at True Ventures. Took four companies public earlier in his career. Focused on running the firm's operations and consulting with portfolio companies.

• 

  Joe Meyer

  Founder and CEO of ExecThread. Previously CEO of HopStop (acquired by Apple) and operating executive at Quigo (acquired by AOL). Career operator turned founder building access to hidden executive opportunities.

• 

  Joe Yaffe

  COO and chief legal officer at Cowboy Space, which is building data centers that run in orbit. Formerly managing partner of Skadden's Palo Alto office and fifteen years at Latham & Watkins, advising founders and CEOs for 31 years.

• 

  Jon Mark

  COO at Vestwell, the digital workplace savings platform serving 25,000 small businesses. Focused on closing the U.S. savings gap through 401(k), 403(b), state auto-IRA, 529, and student debt paydown programs.

• 

  Jonathan Stull

  COO at Handshake, the early-career talent marketplace. Helped scale the three-sided platform to $100M ARR, a $3.5B valuation, and over 500 employees after a career spanning Capitol Hill, emerging-markets PE, and mobile security.

• 

  Justin Etkin

  Co-founder and COO at Tropic, the procurement platform for software-heavy companies. Focused on procurement as a strategic operating function rather than a back-office cost-reduction lever.

• 

  Justin Reilly

  Chief Product Officer at Tucows (NASDAQ: TCX). Previously led product through digital transformation and AI foundation work at Verizon, and worked on machine learning for chronic illness with David Sontag at MIT.

• 

  Kate Henningsen

  Co-founder and COO at Arcadia, the climate technology company opening up energy data. Former litigator using policy and regulation as a wedge to disrupt the U.S. utility monopoly market.

• 

  Ken Weary

  COO at Hotjar, the product experience insights platform. Runs a fully remote 200-person company and has been a digital nomad for over seven years while operating with a family.

• 

  Lance Willett

  Chief Quality Officer at Automattic, the company behind WordPress and WooCommerce. Decade-plus tenure working in the open on software that powers a large share of the web, after years as an independent agency owner.

• 

  Linda Tong

  CEO at Webflow, the visual development platform powering over 300,000 websites. Leading the company's expansion from website builder into AI-accelerated web app and product development.

• 

  Marie Prokopets

  Co-founder and COO at Nira, a document security and access control platform. Previously spent five and a half years at Diageo in strategy, M&A, and innovation.

• 

  Micah Rosenbloom

  Managing Partner at Founder Collective, the seed-stage VC firm behind Uber, Venmo, Hotel Tonight, and ThredUp. Previously co-founder and COO at Brontes Technologies, sold to 3M.

• 

  Munish Gandhi

  Co-founder and COO at Productiv, a SaaS intelligence platform that helps enterprises govern their software portfolio, rationalize spend, and streamline procurement.

• 

  Nathaniel Manning

  Co-founder and COO at Kettle, a reinsurance technology company applying machine learning to catastrophic climate risk. Former White House Presidential Innovation Fellow.

• 

  Nitin Gupta

  COO at Prisma, the open-source ORM and data platform used by millions of developers. Focused on operationalizing hackathons, internal education, and remote team structure.

• 

  Peter Dougherty

  President at Spreedly, the open payments platform. Focused on scaling from $20M to $100M, agentic commerce, AI fraud, and how payments infrastructure needs to evolve for AI-driven transaction volume.

• 

  Peter Rojas

  New products at Mozilla. Peter Rojas co-founded Gizmodo and Engadget, invested as a VC at BetaWorks, and ran new products at Meta. Now he focuses on building new products inside a big company without losing the speed of a startup.

• 

  Rich Wallach

  COO and CFO at Chopra Global, Deepak Chopra's wellness and meditation company. Previously COO of the technology investment banking division at Credit Suisse.

• 

  Rick Marini

  Co-founder, President, and COO of Rails and former COO of Grindr, where he helped lead the turnaround from forced sale to a $2 billion NYSE debut. Founder and CEO of BranchOut, co-founder of Tickle, and angel investor in 60 companies with 15 unicorns.

• 

  Riikka Söderlund

  Chief operating officer at Katana Cloud Inventory. Two decades in marketing before operations, and one of the few COOs to arrive by that route.

• 

  Seth Levine

  Managing Director at Foundry Group and co-author of Capital Evolution. Focused on how capitalism is changing, the shifting role of companies as social arbiters, and what it means for operators.

• 

  Shanaz Hemmati

  Co-founder and COO at ZenBusiness, the platform for starting and running small business G&A, valued at $1.7B. Previously helped grow HomeAway through hyper-growth and IPO.

• 

  Stacey Ryan

  COO at School of Rock, the global music school franchise operating in 19 countries. Known for crisis leadership during COVID and building a community-driven model that goes beyond music education.

• 

  Stephan Jacob

  Co-founder and COO at Cotopaxi, the outdoor brand and certified B Corp built around fighting poverty. Scaled the company past $100M in revenue while embedding sustainability into product development.

• 

  Steve Taylor

  Former Lyft executive who managed the NYC and DC markets through a $500M P&L and the company's run to a $20B IPO. Currently building HipTrain, an at-home fitness app connecting trainers with clients.

• 

  Tao Tao

  Co-founder and COO at GetYourGuide, the travel experiences marketplace that scaled from a dorm-room project to a $2B company. Built the digital infrastructure for a previously offline $300B market.

• 

  Tobias Peggs

  Co-founder and CEO at Square Roots, the indoor urban farming company growing food in controlled environments near major cities. Building a full-stack operation across hardware, software, and farming.

• 

  Valentin Gruber

  COO at HomeToGo, the vacation rental marketplace that went public via SPAC in 2021 at a $1.2B valuation. Known for M&A strategy and scaling the company from a meta-search engine into a full marketplace.

• 

  Valerie Hoecke

  COO at Dia&Co, the plus-size fashion company. Former Global Chief Digital Officer at LVMH Beauty, where she ran digital transformation strategy across 16 brands including Benefit Cosmetics.

• 

  Wade Foster

  Wade Foster built Zapier to 850 people and multiple billions in value without naming a COO. He joins Between Two COOs to explain why exec hiring is a coin flip and why AI adoption is a people problem first.

• 

  Woody Hartman

  COO at Lime, the global micromobility company. Former VP of Global Operations at Lyft, where he was employee number 34 and helped scale the company across a six-year run that included a $20B IPO.