Between Two COO's with Michael Koenig
Between Two COO's brings incredible Chief Operating Officers together to share their insights, advice, and crazy stories. Learn from current and former COO's from companies like Tucows, Automattic, Shippo, Chopra Global, & VC firms.
Episodes
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 $100M ARR, the power of focus and role...
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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 shares how those lessons translate to running a...
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 mus...
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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 importance of tools like Linear and Sto...
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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 LLMs and workflows — from Claude Sonnet t...
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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 clarity
- Predictions for agent-to-agen...
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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 strategic hiring decisions.
AI is poised to sign...
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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-grade compliance.
(33:00) Selecting and uti...
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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, prohibited AI practices, and the potential ...
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 procurement?
[07:00] Common mistakes busines...
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 decision-makers is crucial.
• Non-Traditio...
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 innovative approach to financial welln...
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 and software solutions, and the strat...
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, particularly through the COVID-19 p...
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 conversation introduces Fellow, a SaaS ...
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 book and examine its content, which serves...
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 I dissect the Act's risk-based appr...
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 an insightful discussion on the men...
(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 - 40:47) International Tensions and Investme...
(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 management.
(22:28) Recruitment, Career Growt...
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