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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

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

Get 90 days of Fellow's AI meeting assistant at 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)

Get 90 days of Fellow's AI meeting assistant at fellow.app/coo

In this episode, Doug and I cover:

• Why “AI agent” is more than just a buzzword
• The difference between deflection and resolution in AI-powered support
• How Kustomer structures RevOps, GTM, and forecasting
• What it means to operate with high-context vs. generic playbooks
• How Doug thinks about team structure, ownership, and cross-functional clarity
• Predictions 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

Links

Doug Hanna on LinkedIn - https://www.linkedin.com/in/douglashanna1/

Kustomer - https://www.kustomer.com/

Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514

Between Two COO's - https://betweentwocoos.com