YouTube Video
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.
Subscribe so you don't miss the next one.
#productmanagement #PM #atlassian
About Atlassian:
Behind every great human achievement, there is a team. From medicine and space travel to disaster response and pizza deliveries, we help teams all over the planet advance humanity through the power of software. Our mission is to help unleash the potential of every team.
Connect with Atlassian:
Subscribe: https://www.youtube.com/@atlassian
Follow Atlassian on LinkedIn: https://www.linkedin.com/company/atlassian
Follow Atlassian on Instagram: https://instagram.com/atlassian
Follow Atlassian on X: https://twitter.com/atlassian
Follow Atlassian on Facebook: https://facebook.com/atlassian
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.
Subscribe so you don't miss the next one.
#productmanagement #PM #atlassian
About Atlassian:
Behind every great human achievement, there is a team. From medicine and space travel to disaster response and pizza deliveries, we help teams all over the planet advance humanity through the power of software. Our mission is to help unleash the potential of every team.
Connect with Atlassian:
Subscribe: https://www.youtube.com/@atlassian
Follow Atlassian on LinkedIn: https://www.linkedin.com/company/atlassian
Follow Atlassian on Instagram: https://instagram.com/atlassian
Follow Atlassian on X: https://twitter.com/atlassian
Follow Atlassian on Facebook: https://facebook.com/atlassian
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