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 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.
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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://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
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
