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

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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)