Vision gets the headlines. Execution runs the company.
Conversations with the operators behind the companies you know — with veteran COO host, Michael Koenig.
Featuring leaders from
Greg Keller, JumpCloud CTO on AI Agent Identity & Security
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 beco
All Episodes
60 episodes
Greg Keller, JumpCloud CTO on AI Agent Identity & Security
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 beco
Mar 5, 2026
Seth Levine of Foundry Group on Capital Evolution & AI
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 s
Jan 28, 2026
Brad Feld on Emotional Operating Systems & 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. Br
Jan 20, 2026
Peter Dougherty, Spreedly President on AI, Fraud & Commerce
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 problem
Dec 10, 2025
Harris Clarke, GuideCX COO on Building Trust & Systems
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 c
Nov 13, 2025
Anna Elwood, Cascade COO on Turning Chaos Into Clarity
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
Oct 28, 2025
Lance Willett, Automattic CQO on Powering 45% of the Web
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,
Jul 23, 2025
Linda Tong, Webflow CEO on Running Ops with AI at Scale
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
Jul 8, 2025
Doug Hanna, Kustomer COO on Agentic AI & Modern Ops Teams
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 ope
Jun 4, 2025
Brad Rosen, Sales Assembly President on RevOps & Growth
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 indispensa
Apr 29, 2025
Aydin Mirzaee, Fellow CEO on Pivoting Meetings to AI
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 pivot
Apr 15, 2025
Flick Fisher on the EU AI Act & Its Impact on US Companies
Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo In this insightful episode, Flick Fisher delves deep into the newly enacted European Union Artificial Intelligence Act (EU AI Act), exploring its comprehensive framework aimed at regulating AI with a human-centric, risk-based approach.
Apr 1, 2025
Cut Your SaaS Costs: COO Justin Etkin on Smarter Procurement
In this episode of Between Two COOs, Michael Koenig sits down with Justin Etkin, COO of Tropic.io, to discuss how procurement has evolved into a strategic function in today’s businesses. Justin shares his insights on how companies can use procurement as a growth lever rather than just a cost-saving
Feb 5, 2025
Evan Grossman, True Search MD on Landing a C-Suite Role
In this episode of Between Two COOs, Michael Koenig interviews Evan Grossman, partner and head of the CEO and board practice at True Search, one of the world’s leading executive recruiting firms. Evan shares insights into the hidden C-suite job market, the importance of networking, and how to positi
Jan 21, 2025
Jon Mark, Vestwell COO on Strategy at Multi-Billion Scale
In this insightful episode of Between Two COOs, host Michael Koenig sits down with Jon Mark, the COO of Vestwell, a trailblazing digital platform revolutionizing workplace savings and investment programs. Vestwell is on a mission to close the savings gap in the U.S., serving 25,000 small businesses
Jan 8, 2025
Valentin Gruber, HomeToGo COO on M&A & Going Public
In this episode of 'Between Two COOs,' host Michael Koenig interviews Valentin Gruber, COO of Home2Go. The conversation covers Home2Go's history, its public listing via SPAC in 2021 with a valuation of $1.2 billion, and the company's strategic direction. Valentin discusses their approach to navigati
Jul 16, 2024
Stacey Ryan, School of Rock COO on Crisis Leadership
Empowering Leadership and Innovation with Stacey Ryan of School of Rock In this episode of Between Two COOs, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock, a global music school franchise. Despite common beliefs, the School of Rock predated its namesake 2003 film, with Stace
Apr 23, 2024
Aydin Mirzaee, Fellow CEO on Mastering AI Productivity
In an insightful episode of 'Between Two COOs,' host Michael Koenig converses with Aidan Mirzaee, the founder and CEO of Fellow, about the art and science of optimizing meetings. The discussion dives into the staggering statistics of daily meetings in the U.S., the inception of Fellow as a product t
Apr 9, 2024
Cameron Herold of COO Alliance on Second in Command
Join me, Michael Koenig, on a journey with business guru Cameron Harold, as we celebrate his latest literary achievement, "The Second In Command." Listen in as Cameron, the brain behind COO Alliance, unpacks the essentials of his new book, offering a treasure trove of guidance for CEOs and COOs alik
Feb 13, 2024
EU vs AI: Flick Fisher on the Legal Opinion for US Companies
How you need to plan for the AI Act? What is permissible and isn’t? How the EU will regulate AI? What constitutes AI? 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 partn
Jan 30, 2024
Greg Strickland, Productboard COO on SMB to Enterprise
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
Jan 24, 2024
Tao of GetYourGuide on Building a $2B Travel Giant
Unpack the transformation of travel experiences with me, Michael Koenig, as Tao Tao, COO of GetYourGuide, reveals the secrets behind turning a dorm-room startup into a $2 billion industry titan.
Jan 9, 2024
Allan Christensen, Doist COO on Remote Ops & Hiring
Are you ready for a deep dive into the world of remote work, productivity, and leadership? Let us whisk you away on a journey with our special guest, Alan Christensen, the COO of Duist, a trailblazing SaaS company. Alan’s story, which starts from humble beginnings in a family pipe business, catapult
Dec 19, 2023
Dan Siroker of Rewind.ai & Optimizely on AI & Memory
We're thrilled to welcome Dan Siroker, co-founder and CEO of Rewind, and former CEO and co-founder of Optimizely, to Between Two COOs!
Dec 5, 2023
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