Atlassian: Rachel Wolan: Webflow's CPO on Running 10 Agents at Once in Claude Code

Rachel Wolan runs product, design, and data at Webflow, and she is trying to delete every status meeting on her calendar by the end of the year. In this episode she shows Axel Sooriah exactly how: the builder days that took her org from roughly 15% to 95% building with AI, the one-line field that replaced a recurring roadmap meeting, and a live walkthrough of the system she built in Claude Code on top of Jira Product Discovery to triage feedback, generate mini-specs, and tell her what changed without anyone writing an update.

This is a hands-on episode. The second half is screen share.

What you'll learn:

Why AI fluency does not come from training on how models work, and what builder days do instead

How Rachel took her design team from roughly 15% tool usage to sustained adoption after a single builder day

The rule that changed how her team preps: no meeting with her without a prototype

Why she believes PMs should own evals, and what happens to the ones who don't live at the model layer

The difference between developing something and engineering it, and why a designer and PM should be able to ship to 20 users alone

How she replaced a recurring status meeting with a five-minute field update in Jira Product Discovery

Her live build: auto-triaging sales and partner feedback, pulling the source Gong call, and generating a mini-spec with three candidate solutions

The agent she trained on her own product review transcripts so her team gets her questions when she isn't in the room

Why she runs 5 to 10 Claude Code agents at once, and how she thinks about agent permissions as the real safety question

Chapters:

00:00: Intro

01:07: Welcome to Product in Practice

02:49: From "I use AI" to a team that ships AI products

06:59: The biggest workflow shift: fewer meetings

09:43: How design, product, and data are blurring

11:52: Building in orders of magnitude

13:00: Why scale surfaces corner cases, and what adaptive UX changes

14:28: How the PM role changes: own the evals

17:30: A model swap that moved conversion overnight

18:20: Golden evals and knowing when to tear up the roadmap 19:20: Why reading about AI won't get you there

21:06: The personal apps she built to learn faster

24:40: Hands-on: Jira Product Discovery as the system of record 29:10: Rebuilding triage across sales, partners, and Gong

32:29: Autonomous prototypes and the mini-spec

33:32: Pulling PRDs, tech specs, and launch readiness into one view

37:07: Where this stops, and the real cost of coordination

39:47: How it's built: Claude Code and 5 to 10 agents at once 41:06: Where to draw the line on agent permissions

42:54: One piece of advice: always be building

Connect with Rachel:

LinkedIn:⁠ https://www.linkedin.com/in/rachelwolan/⁠ | X:⁠ https://x.com/rachelwolan⁠ | Website:⁠ https://www.rachelwolan.com/⁠

Connect with Axel:

LinkedIn: https://www.linkedin.com/in/axelsooriah/ | Website:⁠ https://linktr.ee/axelsooriah

About Rachel Wolan:

Rachel Wolan is Chief Product Officer at Webflow, where she leads product, design, and data.She has more than twenty years building product, engineering, design, and data teams. Before Webflow she was VP and GM of Dropbox's core business, serving over 700 million users worldwide, and led Dropbox's AI strategy including the acquisition of Command E. Earlier roles include LiveRamp, Euclid, and Talkdesk. She describes herself as a builder first and an executive second.

About Product in Practice:

Product in Practice is Atlassian's product podcast. Product leaders walk through how they actually work: the frameworks, tools, and decisions behind the craft, with a live demo in every episode. Hosted by Axel Sooriah.

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