How to get your whole team excited about AI (and actually using it) | Brian Greenbaum (product designer at Pendo)
How I AI22 Joulu 2025

How to get your whole team excited about AI (and actually using it) | Brian Greenbaum (product designer at Pendo)

Brian Greenbaum is a Senior Staff Product Designer at Pendo who led a company-wide AI transformation after a personal epiphany while on paternity leave. After experiencing the power of AI coding tools firsthand, he created a structured approach to help his entire product organization adopt AI. In this episode, Brian shares his complete playbook for driving AI adoption across teams, measuring success, and navigating the organizational challenges that come with new technology adoption.


What you’ll learn:

  1. The exact Slack message Brian sent while on paternity leave that kickstarted his company’s AI transformation
  2. How to structure both synchronous and asynchronous AI learning opportunities for maximum adoption
  3. The two-pronged approach that dramatically increased AI tool usage across teams
  4. Why becoming your company’s AI champion is one of the best career moves you can make right now
  5. How to measure AI adoption success with sentiment surveys and clear metrics
  6. The critical role of creating a “golden path” for AI tool usage with legal, security, and finance teams

Brought to you by:

Google Gemini—Your everyday AI assistant

Lovable—Build apps by simply chatting with AI

In this episode, we cover:

(00:00) Introduction to Brian Greenbaum

(01:38) Brian’s paternity leave epiphany that sparked an AI initiative

(05:00) Sending the message that launched a transformation

(12:25) The two-pronged approach: synchronous and asynchronous learning

(17:29) Encouraging experimentation and creative exploration

(18:41) How AI enables designers to move beyond MVP thinking

(22:00) Quick summary of the two-pronged approach

(24:43) Measuring AI adoption

(33:48) Creating a centralized AI knowledge center

(35:58) Building an MCP server to demonstrate AI’s potential

(44:08) Why technical understanding is crucial for non-technical roles

(46:01) Final thoughts

Tools referenced:

• Cursor: https://cursor.com/

• Bolt.new: https://bolt.new/

• Claude: https://claude.ai/

• ChatGPT: https://chat.openai.com/

• Midjourney: https://www.midjourney.com/

• Gemini: https://gemini.google.com/

Other references:

• Pendo: https://www.pendo.io/

• Confluence: https://www.atlassian.com/software/confluence

• Slack: https://slack.com/

Where to find Brian Greenbaum:

LinkedIn: https://www.linkedin.com/in/briangreenbaum/

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

Jaksot(65)

I built a custom Slack inbox. It was easier than you’d think. | Yash Tekriwal (Clay)

I built a custom Slack inbox. It was easier than you’d think. | Yash Tekriwal (Clay)

Yash Tekriwal is the head of education at Clay. A self-described hyper-optimizer, Yash has built multiple custom productivity applications using Perplexity Computer and OpenClaw to manage his overwhel...

8 Huhti 44min

I gave Claude Code our entire codebase. Our customers noticed. | Al Chen (Galileo)

I gave Claude Code our entire codebase. Our customers noticed. | Al Chen (Galileo)

Al Chen is a field engineer at Galileo, an observability platform for AI applications, where he works on the front lines with enterprise customers asking highly technical questions. Despite never havi...

6 Huhti 45min

How to turn Claude Code into your personal life operating system | Hilary Gridley

How to turn Claude Code into your personal life operating system | Hilary Gridley

Hilary Gridley is an entrepreneur, former product leader, and new mom who previously appeared on the podcast discussing AI for managers. She returns to share how she's transformed her approach to pers...

30 Maalis 51min

How Stripe built “minions”—AI coding agents that ship 1,300 PRs weekly from Slack reactions | Steve Kaliski (Stripe engineer)

How Stripe built “minions”—AI coding agents that ship 1,300 PRs weekly from Slack reactions | Steve Kaliski (Stripe engineer)

Steve Kaliski is a software engineer at Stripe who has spent the past six and a half years building developer tools and payment infrastructure. He’s part of the team that created “minions”—Stripe’s in...

25 Maalis 41min

How Microsoft's AI VP automates everything with Warp | Marco Casalaina

How Microsoft's AI VP automates everything with Warp | Marco Casalaina

Marco Casalaina, VP of Core AI Products and AI Futurist at Microsoft, demonstrates how he uses AI tools to automate administrative tasks that typically consume valuable time. Rather than using Warp as...

23 Maalis 34min

From journalist to iOS developer: How LinkedIn’s editor builds with Claude Code | Daniel Roth

From journalist to iOS developer: How LinkedIn’s editor builds with Claude Code | Daniel Roth

Daniel Roth, editor in chief at LinkedIn, went from business writer to iOS app developer, without ever learning how to code. Using Claude Code, Daniel built and shipped multiple production-ready iOS a...

16 Maalis 38min

From Figma to Claude Code and back | Gui Seiz & Alex Kern (Figma)

From Figma to Claude Code and back | Gui Seiz & Alex Kern (Figma)

Most teams are still passing static design files back and forth, and most Figma files are already out of date by the time they reach engineering. Gui Seiz (designer) and Alex Kern (engineer) from Figm...

11 Maalis 40min

Mastering Midjourney: How to create consistent, beautiful brand imagery without complex prompts | Jamey Gannon

Mastering Midjourney: How to create consistent, beautiful brand imagery without complex prompts | Jamey Gannon

Jamey Gannon is an AI creative director who specializes in creating consistent, beautiful brand imagery using AI tools. In this episode, Jamey demonstrates her streamlined workflow for generating cohe...

9 Maalis 49min