Between Two COO's with Michael Koenig

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In this episode, Michael Koenig sits down with longtime friend and colleague Lance Willett, Chief Quality Officer at Automattic—the company behind WordPress and WooCommerce. The two dive deep into the evolution of open source at scale, the overlooked role of technical operations, and how quality shapes everything from uptime to user trust. They also unpack how Automattic is integrating AI across products, lessons from acquiring Tumblr, and the leadership values Lance learned directly from Matt Mullenweg.

Show Notes

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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 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://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 

What is Between Two COO's with Michael Koenig?

Between Two COOs is hosted by veteran COO Michael Koenig and brings together Chief Operating Officers, executives, and business leaders to share real insights on operations, leadership, scaling, AI, and execution. Featuring COOs from companies like LVMH, Vodafone, Automattic, Lime, JumpCloud, Grafana Labs, and Cotopaxi, plus top VCs like Brad Feld and Seth Levine. Whether you're a COO, VP of Ops, founder, or aspiring operator — this is the podcast for people who actually run companies. New episodes weekly. betweentwocoos.com | b2coos.com