Between Two COO's with Michael Koenig

• 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 LinkedInGuideCXMichael Koenig on LinkedInBetween Two COO's WebsiteEpisode Website 

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• 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. Timestamps00:00 – Intro & sponsor01:00 – The chaos of Superstorm Sandy02:00 – Anna’s journey: from theater to tech06:00 – The making of a generalist10:00 – Joining Cascade and fixing retention11:00 – Creating a “working rhythm”14:00 – Governance vs. red tape17:00 – The 5 pillars of strategic maturity19:00 – Turning strategy into execution24:00 – How Cascade uses AI internally28:00 – OKRs, KPIs, and strategy frameworks33:00 – Who owns strategy?36:00 – Rebuilding a business overnight43:00 – Closing thoughts Between Two COO's - https://betweentwocoos.com Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascadeAnna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwoodMichael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514 

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• 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/cooGuest: Lance Willett, Chief Quality Officer at AutomatticTopics 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 Automattic03:00 – 06:30: How Automattic’s open source ethos evolved over 20 years06:30 – 10:30: What it means to be a Chief Quality Officer—Craft × Context10:30 – 15:00: Scaling quality: repo sprawl, signal vs. noise, and auditing15:00 – 20:00: UX details like forms, performance, and speed as quality levers20:00 – 24:00: Driving culture change with standard tooling (Linear, Storybook)24:00 – 28:00: Guardrails for AI experimentation and internal governance28:00 – 32:00: AI at Automattic: support bots, contextual UI, AI site builder32:00 – 36:00: Competing with Webflow, Wix, and Squarespace through innovation36:00 – 38:30: Balancing ecosystem contribution with revenue and investor pressure38:30 – 41:00: Lessons from stabilizing Tumblr: cost, culture, safety, turnover41:00 – 44:00: Automattic’s long-term challenge: bounded optimism and focus44:00 – 46:30: Leadership wisdom from Matt Mullenweg: details always matter46:30 – 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 timeCredit: Casey Winters – someone you should have on this show if you haven’t alreadyhttps://caseyaccidental.com/ Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpressMichael Koenig - https://linkedin.com/in/michael-koenig514 Between Two COO's - https://betweentwocoos.com 

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• 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/cooWhy 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) 

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• 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/cooIn 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 LinksDoug Hanna on LinkedIn - https://www.linkedin.com/in/douglashanna1/Kustomer - https://www.kustomer.com/Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514Between Two COO's - https://betweentwocoos.com 

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