Automattic Chief Quality Officer, Lance Willett, on What It Takes to Power 45% of the Web and Learning from a $250K Mistake
Description
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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
United States
