. | Between Two COO's

Dec. 10, 2025

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 proble…

Nov. 13, 2025

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 …

Oct. 28, 2025

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-exec...

July 23, 2025

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,…

July 8, 2025

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 …

June 4, 2025

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 ope…

April 29, 2025

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 indispens…

April 15, 2025

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 pivo…

April 1, 2025

AI and Privacy: Navigating the EU's New AI Act & the Impact on US Companies with Flick Fisher

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…

Feb. 5, 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…

Jan. 21, 2025

True Search Managing Director Evan Grossman on how to land your next 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 posit…

Jan. 8, 2025

Vestwell COO Jon Mark on applying strategy and tactics to build a multi-billion dollar company

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…

July 16, 2024

HomeToGo COO Valentin Gruber Talks M&A, Strategic Planning, and Taking the Multi-Billion Dollar Company 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 navigat…

April 23, 2024

School of Rock COO Stacey Ryan on Navigating Crises, Change, Leadership, and Empowerment

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 Stac…

April 9, 2024

Fellow CEO Aydin Mirzaee on Mastering Productivity and Efficiency with AI

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 …

Feb. 13, 2024

How to delegate, lead, fix problems, hire and promote, and be the second in command with Cameron Herold of COO Alliance and 1-800-got-junk

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 ali…

Jan. 30, 2024

EU vs AI: What You Need to Know About the EU's AI Act - The Legal Opinion with Flick Fisher, Partner at Fieldfisher

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 part…

Jan. 24, 2024

Productboard COO Greg Strickland on how to balance growth and innovation, collecting mentors and personal development, managing through change, SMB to enterprise shift, and the competitive advantage of startups

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. 9, 2024

Get Your Guide COO Tao on Building a $2 Billion Dollar Travel Experience Giant

Unpack the transformation of travel experiences with me, Michael Kanig, as Tao Tao, COO of GetYourGuide, reveals the secrets behind turning a dorm-room startup into a $2 billion industry titan. We're setting the stage for a fascinating tale of innovation, strategy, and resilience that's reshaping t…

Guest: Tao Tao

Dec. 19, 2023

Doist COO Allan Christensen on remote ops, perfecting hiring, designing ops for career development, the ideal employee feedback loop

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, catapul…

Dec. 5, 2023

Rewind.ai & Optimizely CEO & Founder, Dan Siroker, on augmenting human memory with AI, building Optimizely, AI in operations, privacy and security, hiring and building extraordinary teams, and AI's impact on STEM education

We're thrilled to welcome Dan Sroker, co-founder and CEO of Rewind, and former CEO and co-founder of Optimizely, to Between Two COOs! This episode centers around an eye-opening conversation about the potential of AI to augment human memory, transforming every digital interaction into an AI-able, se…

Guest: Dan Siroker

Nov. 21, 2023

Arcadia COO, Kate Hennigsen, on Clean Tech and Disrupting the Energy Market, Non-Traditional Backgrounds for Working in Tech (and Ops!), Energy Regulation, M&A, Board, Risk, and Cash Management, & the Power of a Well Written Cold Emai

The compelling Kate Hemington, co-founder and COO of Arcadia, joins us for a deep dive into the revolutionary world of clean tech and the disruption of the energy market. Her unique insights, stemming from her academic background at the University of Oxford and experience in corporate litigation, s…

Guest: Kate Henningsen

Oct. 17, 2023

Perfecting Remote Work Operations with Darren Murph, Fmr Gitlab VP Remote

We're thrilled to present a fascinating conversation with Daren Murph, acknowledged as the Oracle of Remote Work by none other than CNBC. Prepare for a deep dive into the critical operations of remote companies, with a spotlight on low context communication. In our discussion, we unpack the signifi…

Guest: Darren Murph

Sept. 26, 2023

Prisma COO, Nitin Gupta, explains tech to my mom, operationalizing hackathons, the balance of commercializing open-source, planning, and a team psychologist

Prisma COO Nitin Gupta joins to explain Prisma to my mom, how Prisma University educates internally, and technical team members share knowledge. He discusses operationalizing hackathons, remote team issues, all-hands meetings, organization structure, and open-sourcing processes. Learn how Prisma em…

Guest: Nitin Gupta