Between Two COO's with Michael Koenig

Get 90 days of Fellow free at Fellow.ai/coo In this episode, Michael Koenig speaks with Greg Keller, co-founder and CTO of JumpCloud, about identity access management and why it’s becoming one of the most important operational systems in the age of AI. Greg explains how traditional identity systems were designed for office-based companies running Microsoft infrastructure and why that model broke a...

Get 90 Days of Fellow's incredible AI notetaker for free at fellow.ai/coo Guest: Seth Levine Book: Capital Evolution Podcast: Between Two COOs Host : Michael Koenig What we cover Why Seth wrote Capital Evolution and why now Why today’s economic shift is structural, not cyclical How power has moved from public institutions to businesses What companies are being asked to carry that they weren’t buil...

Get Brad's new book, Give First . 00:00 — Cold open: “Something new is fucked up in my world every day” 02:00 — The Yoda t-shirt story + the mythology of Brad Feld 04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation 07:00 — Why giving isn’t altruism — and how it works in complex systems 10:00 — Positive-sum vs. zero-sum: tennis, trust, and long games 13:00 — Does giving create ou...

This episode goes deep into the mechanics of scaling a company from steady growth to breakout velocity. Peter shares how Spreedly quadrupled ARR growth in his first year without increasing OPEX, why the “right people pointed at the right problems” is everything, and how to decide which problems are existential versus learn-as-you-go. We dissect how go-to-market organizations evolve from $20M to $1...

Get 90 Days of Fellow's AI Meeting Assistant FREE at fellow.ai/coo   This week on Between Two COOs , Michael sits down with Harris Clarke , COO at GuideCX , to talk about what steady leadership actually looks like inside fast-changing companies. Harris started his career in protocol and operations for the U.S. Department of State , where “process” wasn’t just a buzzword — it was survival. He share...

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 b...

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo Guest: Lance Willett, Chief Quality Officer at Automattic Topics Covered: How Automattic’s open source culture evolved over 20 years What a Chief Quality Officer actually does—and why it matters Quality = Craft × Context, and how that feedback loop scales Automattic’s AI strategy: support bots, contextual UI, and site generation The i...

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo Why Linda still codes on weekends — and what it teaches her about the future of AI (6:00) How AI is changing what Webflow builds — and how fast they build it (3:30–13:00) What happens when websites are no longer built just for humans (14:00) The rise of AEO (Answer Engine Optimization) and what it means for ops (17:00–21:00) Favorite L...

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo In this episode, Doug and I cover: Why “AI agent” is more than just a buzzword The difference between deflection and resolution in AI-powered support How Kustomer structures RevOps, GTM, and forecasting What it means to operate with high-context vs. generic playbooks How Doug thinks about team structure, ownership, and cross-functional...

Get 90 days free with Fellow's AI Meeting Assistant - https://fellow.app/coo   Key Takeaways: RevOps aligns and optimizes sales, marketing, and customer success, ensuring efficient and sustainable growth. Effective RevOps requires balancing strategic planning, data-driven analytics, and tactical execution. Successful RevOps integration hinges on clear communication, cultural alignment, and strateg...

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo Timestamps: (02:00) Fellow’s shift from productivity tool to AI assistant. (07:00) Implementing large-scale organizational change. (13:00) Managing change and internal communications. (20:00) Moving toward an agentic, automated workflow future. (23:00) Unexpected real-world AI uses at Fellow. (29:00) Privacy, security, and enterprise-...

Try Fellow's AI Meeting Copilot - 90 days FREE - fellow.app/coo AI and Privacy: Navigating the EU's New AI Act with Flick Fisher In this episode of Between Two COOs, host Michael Koenig welcomes back Flick Fisher, an expert on EU privacy law. They dive deep into the newly enacted EU Artificial Intelligence Act and its implications for businesses globally. They discuss compliance challenges, prohib...

Don't forget to check out www.fellow.app/coo for a 90-day free trial of their AI Meeting Assistant. [00:00] Introduction – Michael introduces Fellow as a trusted AI meeting assistant. [01:00] Welcome to Between Two COOs – Introducing Justin Etkin and Tropic.io. [02:00] The evolution of procurement – From cost-cutting to strategic value creation. [05:00] When should companies start formalizing proc...

This episode is powered by Fellow AI Meeting Assistant. Get 90 days free at fellow.app/coo Key Takeaways: • Hidden C-Suite Job Market: The majority of C-level roles are filled through networking, talent partners, and executive recruiters before job postings are even considered. • Role of Networking: Building strong relationships within your industry and maintaining top-of-mind positioning with dec...

Episode Overview In this episode of Between Two COOs , host Michael Koenig interviews Jon Mark, COO of Vestwell, a leading provider of digital platforms for workplace savings and investment programs. Vestwell supports nearly 25,000 small businesses, over a million savers, and $25 billion in assets under management across all 50 states. They discuss Vestwell’s mission to close the savings gap, its...

In this episode of Between Two COOs, host Michael Koenig sits down with Valentin Gruber, COO of HomeToGo, to explore the inner workings of the vacation rental aggregator and its strategy. HomeToGo went public via a SPAC in 2021, reaching a valuation of $1.2 billion after raising $150 million in VC funding. Valentin shares insights into the company’s growth, its approach to balancing marketplace an...

Navigating Leadership and Innovation at School of Rock with Stacey Ryan In this episode of Between Two COOs, host Michael Koenig interviews Stacey Ryan, the COO of School of Rock - a global music school franchise. Stacey debunks a common misconception about the business's origin, noting it predated and inspired the 2003 film. She discusses the operational challenges of managing a global franchise,...

Maximizing Meeting Efficiency and Navigating Management Challenges: Insights from Aidan Mizrahi of Fellow This episode delves into the complexities and potential inefficiencies of meetings in the professional world, emphasizing the staggering number of unproductive meetings held daily. Highlighting the innovative approach of Shopify in canceling recurring meetings to save significant time, the con...

Presented by Fellow.app. Streamline your meetings and make them more efficient and meaningful. Get Fellow for you and your team today. Head to https://fellow.app/coo/ to get started and start having better meetings.   (00:12) Advice for CEOs and COOs   This chapter welcomes Cameron Harold, the founder of COO Alliance and author of "The Second In Command," as we celebrate the release of his new boo...

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 partner at Fieldfisher. As the digital age accelerates, the European Union is setting a precedent with the AI Act, a groundbreaking legislation designed to navigate the complex terrain of artificial intelligence. Flick and...

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 strategic 'no' can pave the way for others' development and align with company goals. Listen in for...

(01:20 - 02:44) The Travel Experience Market's Growth (04:36 - 06:03) Peer to Peer Tour Guide Platform (07:27 - 09:26) Learning and Customer Obsession Importance (12:35 - 13:56) Creativity and Execution in Strategy (16:11 - 17:06) Identifying Core Values for Company Culture (21:48 - 23:03) Accelerating Digitization and the QR Code (36:32 - 37:43) Investment Strategy and Flywheel Approach (39:48 -...

(00:12) Interview With Remote COO Alan Christensen   COO Alan Christensen shares his journey and Duist's success without institutional investment, pioneering remote work and dividing responsibilities with CEO.   (11:48) Future of Remote Work and Communication   Remote work's significance in shaping the future, utilizing asynchronous communication, transparency, and documentation for effective mana...

(05:11 - 05:38) Memory and the Evolving Digital Age (06:56 - 08:05) Tech and Memory Retrieval (11:40 - 12:51) Chat GPT and Data Privacy Integration (17:34 - 18:44) Leveraging AI for Company Augmentation (22:34 - 23:47) AI for Efficiency and Exceptional Hiring (30:31 - 31:01) Pivoting to Capture Meeting Data (38:38 - 39:00) COO and Chief of Staff Collaboration (43:27 - 44:27) Using Cultural Values...

(00:12) Clean Tech and Disrupting Energy Market (06:15) Community Solar and Renewable Energy Innovation (15:37) Data Platform and Energy Transformation (24:21) Acquisitions, Integration, and Board Composition (29:05) Startup Board Management and Risk Balancing (35:51) Leadership, Growth Mindset, and Overcoming Challenges (42:18) Connecting Through Cold Emails (00:12) Clean Tech and Disrupting Ener...