Between Two COO's with Michael Koenig

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 presidency * The “right person, right problem” framework * One-way vs two-way doors for staffing big problems * How to scale a GTM org from $20M to $100M * Why open payments replaces orchestration * Spreedly’s unique market position and 15-year head start * Agent to agent commerce and Google’s new payments protocol * How AI changes the velocity of money movement * Fraud orchestration and Spreedly’s acquisition of Dodgeball * Balancing profitable growth vs growth at all costs * Perception vs reality in leadership * Peter’s wildest “I never thought I’d see that” story

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 [https://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 style * The “three P’s” framework for productive meetings * Why decision speed is overrated — and what Harris means by “Did anyone die or go to jail?” * What he learned from executive coaching and board feedback * How GuideCX built a new product category around customer onboarding * How AI is quietly reshaping how he manages teams and prepares communications * Why calm is a competitive advantage during crisis moments like SVB Michael 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 [https://www.linkedin.com/in/harris-clarke-26605946/] GuideCX [http://guidecx.com/] Michael Koenig on LinkedIn [https://linkedin.com/in/michael-koenig514 ] Between Two COO's Website [https://betweentwocoos.com ] Episode Website [https://betweentwocoos.com/harris-clarke-guidecx ]

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

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 [https://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 importance of tools like Linear and Storybook in enforcing quality * How Automattic balances speed, risk, and governance with AI experimentation * Lessons from stabilizing Tumblr during its post-acquisition reboot * Prioritization and the dangers of unbounded optimism * Leadership takeaways from working closely with Matt Mullenweg 🕰️ TIME MAP 00:00 – 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://brodo.com/] https://fullstackleader.blog/ [https://fullstackleader.blog/] (work topics: WordPress, tech, productivity, quality, & more) https://lance.blog/ [https://lance.blog/] (fun stuff: poems, stories, links; photos “on the go”) https://linear.app/ [https://linear.app/] https://clay.earth/ [https://clay.earth/]via https://automattic.com/2025/06/12/automattic-welcomes-clay/ [https://automattic.com/2025/06/12/automattic-welcomes-clay/]   Companies with dedicated quality efforts: https://anthonyhobday.com/blog/20240914.html [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/ [https://caseyaccidental.com/]   Episode webpage - https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpress [https://www.betweentwocoos.com/automattic-chief-quality-officer-lance-willett-wordpress] Michael Koenig - https://linkedin.com/in/michael-koenig514  [https://linkedin.com/in/michael-koenig514 ] Between Two COO's - https://betweentwocoos.com  [https://betweentwocoos.com]

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 [https://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)