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Between Two COO's with Michael Koenig

Michael Koenig

Between Two COOs is hosted by veteran COO Michael Koenig and brings together Chief Operating Officers, executives, and business leaders to share real insights on operations, leadership, scaling, AI, and execution. Featuring COOs from companies like LVMH, Vodafone, Automattic, Lime, JumpCloud, Grafana Labs, and Cotopaxi, plus top VCs like Brad Feld and Seth Levine. Whether you're a COO, VP of Ops, founder, or aspiring operator — this is the podcast for people who actually run companies. New episodes weekly. betweentwocoos.com | b2coos.com

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#68
Tuesday · 40 min
The AI Bubble Has a Due Date. It's 2029 | Paul Kedrosky, SK Ventures
Paul Kedrosky of SK Ventures says AI capex is driving up to 70 percent of US GDP growth, and most of it is now borrowed. He walks through the money map, the 2029 maturity wall, why AI tokens are a deflationary commodity, and three ways the AI bubble reaches companies that never touch a data center.
#67
September 16 · 54 min
Lior Eldan, Moburst COO on Reinventing the Marketing Agency Before AI Eats It
Lior Eldan, co-founder and COO of Moburst, has reinvented what his agency sells three times, from app store optimization to AI products. He explains why replacing people with AI is backward, why managers still have to do the work, and why automating a broken process just ends up blaming the AI.
#66
August 18 · 36 min
Joe Yaffe, COO at Cowboy Space, on Whether Data Centers in Space Are Cheaper
Part 2 of 2. Joe Yaffe, COO and chief legal officer at Cowboy Space, on the harder question. Not whether you can put a data center in orbit, but whether it earns its money. The cost test the company holds itself to, the seven agencies that regulate it, why a rocket engine is tuned to sit beside an explosion, and what actually keeps him up at night.
#65
August 11 · 52 min
Joe Yaffe (Cowboy Space): From Big Law to Orbit, Part 1 of 2
Joe Yaffe spent 31 years as one of the top lawyers in Silicon Valley and ran Skadden's Palo Alto office. Then a client called to say he was thinking about building space lasers, and Joe told him he would come along. He is now COO and chief legal officer at Cowboy Space, building data centers that run in orbit. Part 1 of 2.
#64
July 29 · 45 min
Riikka Söderlund, Katana COO, on Why AI Won't Know Your Product Exists
Riikka Söderlund is the chief operating officer at Katana Cloud Inventory. Her argument is that AI search cannot read your branding or your homepage, only your product data, and a product that is out of stock does not get surfaced at all. She also explains why she came to operations from marketing rather than sales, and why she runs OKRs on a six-week cadence rather than quarterly.
#63
July 21 · 38 min
Rick Marini on the Day-One Speech That Turned Grindr Around
Rick Marini, co-founder of Rails and former COO of Grindr, on why he would rather be a great COO than a good CEO. He breaks down the Grindr turnaround from forced sale to a $2 billion NYSE debut, the day-one speech that won over a burned-out team, and the IQ test pivot that saved Tickle in the dot-com crash.
#62
July 15 · 50 min
Zapier CEO Wade Foster on Why AI Is a People Problem, Not a Tech Problem
Wade Foster, Co-founder and CEO of Zapier, explains why he has never named a COO despite scaling to 850 people and multiple billions in value. He breaks down the 2023 code red triggered by GPT-4, the 2024 pricing overhaul that gave revenue back to customers, and why external COO hires are a coin flip.
#61
July 2 · 37 min
Zulema Quintans, COO of Noda, on Why Your OKRs Don't Get Done
Zulema Quintans, COO of Noda, on building an energy management software company for the commercial built environment. She explains why AI's real winners pair it with a strong service layer, how she runs OKRs as an operating system, and how AI cut a task that took weeks down to hours.
#60
June 16 · 46 min
Peter Rojas, New Products at Mozilla, on Why Ideas Don't Decide Success
Peter Rojas co-founded Gizmodo and Engadget, invested as a VC at BetaWorks, and ran new products at Meta. Now leading new products at Mozilla, he joins Michael Koenig to break down what determines success or failure for new products and companies, how building new products inside a big company differs from a startup, why coordination is the real constraint at scale, and the strangest founder decision he has ever seen.
#59
March 5 · 32 min
AI Agents Need Logins Too: Identity, Security, and the Future of AI | Greg Keller, CTO, JumpCloud
Get 90 days of Fellow free at Fellow.ai/coo AI is moving fast. Most companies are focused on tools. The real challenge may be identity. In this episode of Between Two COOs, Michael Koenig sits down with Greg Keller, co-founder and CTO of JumpCloud, to explore why identity access management is becoming the control layer for modern companies and the foundation for secure AI adoption. Greg explains how identity systems evolved from the Microsoft Active Directory era to today’s cloud-first world
#58
January 28 · 48 min
Seth Levine of Foundry Group on Capital Evolution, AI, and the Future of Company Leadership
Seth Levine, Managing Director at Foundry Group and co-author of Capital Evolution, joins Between Two COOs to talk about how the American economy is changing - and what that means for the people actually running companies. This is not a theoretical conversation. Seth explains why this moment is a structural shift, not a cycle. We talk about how power has moved from government to business, why companies are now carrying responsibilities they were never designed for, and how AI is accelerating bo
#57
January 20 · 57 min
Brad Feld On The Emotional Operating System of Great Leaders and Giving First
Brad Feld, co-founder of Techstars and Foundry Group, joins Michael to unpack the philosophy behind his book Give First—but this isn’t a standard VC retrospective. It’s a raw, thoughtful conversation about the operational and emotional systems behind generosity, mentorship, identity, and meaning. Brad shares stories from the early Boulder startup days, what most people misunderstand about giving, how to mentor without directing, and why trust is the foundation of everything that matters. Along t
#56
Dec 10, 2025 · 45 min
AI, Fraud, and the Next Era of Commerce with Peter Dougherty, President of Spreedly
Peter Dougherty, President of Spreedly, breaks down how payments are changing, why “open payments” is the new orchestration, and how AI and agentic systems will reshape commerce at a structural level. We talk scaling from 20M to 100M, building teams for inflection points, finding existential problems vs noise, and why perception is often more important than raw numbers. We also cover fraud, Spreedly’s acquisition of Dodgeball, and what agent to agent payments unlock in the next decade.
#55
Nov 13, 2025 · 58 min
The Power of Calm: GuideCX COO Harris Clarke on Building Trust and Systems That Hold
Harris Clarke, COO at GuideCX, joins Michael to unpack what it means to lead when everything feels like it’s shifting under your feet. From learning precision and process in the U.S. Department of State to running operations in a high-growth SaaS company, Harris shares how trust, clarity, and calm create real stability in an organization.
#54
Oct 28, 2025 · 38 min
The COO Who Turns Chaos Into Clarity - Anna Elwood of Cascade
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 COOs, 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. She explains how to create an “oper
#53
Jul 23, 2025 · 52 min
Automattic Chief Quality Officer, Lance Willett, on What It Takes to Power 45% of the Web and Learning from a $250K Mistake
Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo In this episode, Michael Koenig sits down with longtime friend and colleague Lance Willett, Chief Quality Officer at Automattic—the company behind WordPress and WooCommerce. The two dive deep into the evolution of open source at scale, the overlooked role of technical operations, and how quality shapes everything from uptime to user trust. They also unpack how Automattic is integrating AI across products, lessons from acquiring Tum
#52
Jul 8, 2025 · 1 hr 12 min
Linda Tong, Webflow CEO, on the new web, AI-powered ops, and how they run Webflow
Get 90 days of Fellow's AI meeting assistant at fellow.app/coo In this episode of Between Two COOs, I’m joined by Linda Tong, the CEO of Webflow. You probably know Webflow as one of the most popular visual development platforms on the internet, powering over 300,000 websites. What you may not know is that Webflow is going all-in on AI – not just in product, but across operations, marketing, and internal tooling. Linda and I get into the hard questions: • What happens to websites when bots, no
#51
Jun 4, 2025 · 46 min
Kustomer COO & President, Doug Hanna, on Building Agentic AI, Running Sales, and Structuring Modern Ops Teams for the AI Era
Get 90 days of Fellow's AI meeting assistant at fellow.app/coo Doug Hanna, President & COO of Kustomer (acquired by Meta), returns to the pod for Episode 51 of Between Two COOs. This time, we’re talking about AI—specifically agentic AI—and how it’s reshaping customer service, GTM workflows, and operational leadership. Doug shares real examples of how Kustomer’s AI agents are resolving tickets, not deflecting them—and why the real power lies in agent-to-agent collaboration. We also cover RevOps
#50
Apr 29, 2025 · 46 min
Sales Assembly President, Brad Rosen, on Unlocking Growth and Why RevOps Is Critical for Sustainable Scaling
In this episode of Between Two COOs, Brad Rosen, President at Sales Assembly, takes us deep into the world of Revenue Operations (RevOps)—a critical function focused on aligning and optimizing sales, marketing, and customer success operations. Brad shares insights on why RevOps has become indispensable in driving sustainable and efficient growth, highlighting practical ways organizations can effectively leverage this function. He explores the challenges of defining and scaling RevOps, breaking d
#49
Apr 15, 2025 · 47 min
The Bold Pivot: From Meetings to AI with Aydin Mirzaee, CEO of Fellow
Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo In this episode, Aydin Mirzaee, CEO and founder of Fellow, returns to discuss Fellow’s dramatic evolution from a meeting productivity tool into a full-fledged AI-powered operations assistant. Aydin shares insights into how Fellow pivoted successfully to an AI-first strategy, highlighting both the internal transformation and external market demands driving the shift. Key themes include implementing AI at scale, navigating significan

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