Between Two COO's with Michael Koenig

Michael Koenig
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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.

  1. Seth Levine of Foundry Group on Capital Evolution, AI, and the Future of Company Leadership

    JAN 28

    Seth Levine of Foundry Group on Capital Evolution, AI, and the Future of Company Leadership

    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 coverWhy Seth wrote Capital Evolution and why nowWhy today’s economic shift is structural, not cyclicalHow power has moved from public institutions to businessesWhat companies are being asked to carry that they weren’t built forHow AI fits into this broader realignmentEarly signals that companies are adapting well to AIWhat strong executive teams do differently during uncertaintyCommon leadership traps when change happens too fastA real crisis from a portfolio company and what the executive team did wellThe new leadership muscle operators need for the next decadeEpisode Chapters / Timestamps00:00 – Introduction 01:40 – Seth’s 30-second pitch for Capital Evolution 04:05 – Why this shift is structural, not cyclical 07:20 – What’s broken in the current economic model 11:00 – The power shift from government to business 15:10 – What leaders are quietly losing 18:45 – Where AI fits into this realignment 23:30 – What boards see when AI adoption works 28:05 – How strong executive teams handle uncertainty 33:40 – Leadership traps during rapid change 38:10 – A crisis inside a portfolio company 44:00 – The new muscle operators must build 48:50 – A moment Seth never thought he’d see

    48 min
  2. Brad Feld On The Emotional Operating System of Great Leaders and Giving First

    JAN 20

    Brad Feld On The Emotional Operating System of Great Leaders and Giving First

    Get Brad's new book, Give First. 00:00 — Cold open: “Something new is f****d 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 outcomes, or just energy? 16:00 — Why Brad writes books: longform thinking as meaning-making 20:00 — Searching for meaning through mentorship and reflection 23:00 — “I hate the phrase pattern recognition” — mentorship done right 28:00 — The power dynamic between founders and mentors 32:00 — Management through commitment, not control 35:00 — Agile as an operating system for accountability 38:00 — Emotional intelligence and the role of executive coaches 41:00 — Mentor vs. coach vs. therapist vs. advisor 45:00 — Trust as the foundation of all high-leverage relationships 47:30 — Wild story: when the second floor of Sphero’s building collapsed 52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice 55:00 — Closing thoughts on being the Bill Murray of venture capital

    57 min
  3. AI, Fraud, and the Next Era of Commerce with Peter Dougherty, President of Spreedly

    12/10/2025

    AI, Fraud, and the Next Era of Commerce with Peter Dougherty, President of Spreedly

    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 separation, and how to keep silos aligned around one customer story. Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop. We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch. Topics Covered: How Peter defines the journey to presidencyThe “right person, right problem” frameworkOne-way vs two-way doors for staffing big problemsHow to scale a GTM org from $20M to $100MWhy open payments replaces orchestrationSpreedly’s unique market position and 15-year head startAgent to agent commerce and Google’s new payments protocolHow AI changes the velocity of money movementFraud orchestration and Spreedly’s acquisition of DodgeballBalancing profitable growth vs growth at all costsPerception vs reality in leadershipPeter’s wildest “I never thought I’d see that” story

    46 min
  4. The Power of Calm: GuideCX COO Harris Clarke on Building Trust and Systems That Hold

    11/13/2025

    The Power of Calm: GuideCX COO Harris Clarke on Building Trust and Systems That Hold

    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 shares how those lessons translate to running a modern SaaS organization and why purpose, process, and payoff are the anchors of any good meeting. They dig into: How government discipline shaped Harris’s operating styleThe “three P’s” framework for productive meetingsWhy decision speed is overrated — and what Harris means by “Did anyone die or go to jail?”What he learned from executive coaching and board feedbackHow GuideCX built a new product category around customer onboardingHow AI is quietly reshaping how he manages teams and prepares communicationsWhy calm is a competitive advantage during crisis moments like SVBMichael also gives context at the top: this episode was recorded across two sessions, after a recording issue mid-interview (and yes, he’s now officially a Riverside convert). It’s a conversation about building trust, running tight systems, and keeping your head when everything around you is changing. Harris Clarke on LinkedIn GuideCX Michael Koenig on LinkedIn Between Two COO's Website Episode Website

    58 min
  5. The COO Who Turns Chaos Into Clarity - Anna Elwood of Cascade

    10/28/2025

    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-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 “operating rhythm” that keeps teams aligned across time zones, the tension between governance and red tape, and how Cascade helps leaders link vision to measurable execution. The conversation dives deep into AI’s role in operations, the future of hybrid work, and what it takes to move from chaos to clarity in a global startup.   Anna’s storytelling — especially her account of leading through Superstorm Sandy — highlights what real-time operational leadership looks like when everything goes sideways.   Timestamps 00:00 – Intro & sponsor 01:00 – The chaos of Superstorm Sandy 02:00 – Anna’s journey: from theater to tech 06:00 – The making of a generalist 10:00 – Joining Cascade and fixing retention 11:00 – Creating a “working rhythm” 14:00 – Governance vs. red tape 17:00 – The 5 pillars of strategic maturity 19:00 – Turning strategy into execution 24:00 – How Cascade uses AI internally 28:00 – OKRs, KPIs, and strategy frameworks 33:00 – Who owns strategy? 36:00 – Rebuilding a business overnight 43:00 – Closing thoughts   Between Two COO's - https://betweentwocoos.com  Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascade Anna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwood Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514

    38 min
  6. Automattic Chief Quality Officer, Lance Willett, on What It Takes to Power 45% of the Web and Learning from a $250K Mistake

    07/23/2025

    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 Guest: Lance Willett, Chief Quality Officer at Automattic Topics Covered: How Automattic’s open source culture evolved over 20 yearsWhat a Chief Quality Officer actually does—and why it mattersQuality = Craft × Context, and how that feedback loop scalesAutomattic’s AI strategy: support bots, contextual UI, and site generationThe importance of tools like Linear and Storybook in enforcing qualityHow Automattic balances speed, risk, and governance with AI experimentationLessons from stabilizing Tumblr during its post-acquisition rebootPrioritization and the dangers of unbounded optimismLeadership takeaways from working closely with Matt Mullenweg🕰️ Time Map00:00 – 03:00: Intro and Lance’s journey from freelancer to Automattic 03:00 – 06:30: How Automattic’s open source ethos evolved over 20 years 06:30 – 10:30: What it means to be a Chief Quality Officer—Craft × Context 10:30 – 15:00: Scaling quality: repo sprawl, signal vs. noise, and auditing 15:00 – 20:00: UX details like forms, performance, and speed as quality levers 20:00 – 24:00: Driving culture change with standard tooling (Linear, Storybook) 24:00 – 28:00: Guardrails for AI experimentation and internal governance 28:00 – 32:00: AI at Automattic: support bots, contextual UI, AI site builder 32:00 – 36:00: Competing with Webflow, Wix, and Squarespace through innovation 36:00 – 38:30: Balancing ecosystem contribution with revenue and investor pressure 38:30 – 41:00: Lessons from stabilizing Tumblr: cost, culture, safety, turnover 41:00 – 44:00: Automattic’s long-term challenge: bounded optimism and focus 44:00 – 46:30: Leadership wisdom from Matt Mullenweg: details always matter 46:30 – 49:00: Lance’s $250K mistake—and what it taught him about leadership   https://brodo.com/ (our other sponsor 😂) https://fullstackleader.blog/ (work topics: WordPress, tech, productivity, quality, & more) https://lance.blog/ (fun stuff: poems, stories, links; photos “on the go”) https://linear.app/ https://clay.earth/ via https://automattic.com/2025/06/12/automattic-welcomes-clay/   Companies with dedicated quality efforts: https://anthonyhobday.com/blog/20240914.html   > While fixing small bugs might not 10x your growth overnight > Not fixing them will make 10x growth impossible over time Credit: Casey Winters – someone you should have on this show if you haven’t already https://caseyaccidental.com/   Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpress Michael Koenig - https://linkedin.com/in/michael-koenig514  Between Two COO's - https://betweentwocoos.com

    53 min
  7. Linda Tong, Webflow CEO, on the new web, AI-powered ops, and how they run Webflow

    07/08/2025

    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 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 to custom GPTs (23:00–26:00) How Linda builds a culture of innovation — and why bad ideas are worth celebrating (29:00) Leading through operational ambiguity and defining what to say “no” to (49:00) How product thinking helps Linda prioritize and run the business (54:00) Creating an actual in-office “innovation lab” — and what worked (1:04:00) Wild story: how her team navigated the SVB collapse weekend (1:08:00)

    1h 13m
  8. Kustomer COO & President, Doug Hanna, on Building Agentic AI, Running Sales, and Structuring Modern Ops Teams for the AI Era

    06/04/2025

    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 In this episode, Doug and I cover: Why “AI agent” is more than just a buzzwordThe difference between deflection and resolution in AI-powered supportHow Kustomer structures RevOps, GTM, and forecastingWhat it means to operate with high-context vs. generic playbooksHow Doug thinks about team structure, ownership, and cross-functional clarityPredictions for agent-to-agent communication: “Your AI agent will talk to my AI agent—and we’ll both just read the summary.”Timestamps: (02:00) Defining agentic AI in customer service (06:30) From deflection to resolution: Kustomer’s AI in action (10:15) How AI is changing the org chart and team design (14:00) The problem with low-context playbooks (17:45) RevOps structuring and ownership (22:00) Forecasting: visibility vs. execution (27:00) AI tooling, integration, and buyer psychology (31:00) Agent-to-agent interactions and AI futurecasting (34:30) What Doug’s watching next in ops and AI   Links Doug Hanna on LinkedIn - https://www.linkedin.com/in/douglashanna1/ Kustomer - https://www.kustomer.com/ Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514 Between Two COO's - https://betweentwocoos.com

    46 min
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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.

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