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

How I AI

2025/12/22
How I AI

How I AI

2025/12/22

Shownote

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 [https://ai.dev/]—Your everyday AI assistant Lovable [https://lovable.dev/]—Build apps by simply chatting with AI — In this episode, we cover: (00:00 [https://www.youtube.com/watch?v=yaG70VotukE]) Introduction to Brian Greenbaum (01:38 [https://www.youtube.com/watch?v=yaG70VotukE&t=98s]) Brian’s paternity leave epiphany that sparked an AI initiative (05:00 [https://www.youtube.com/watch?v=yaG70VotukE&t=300s]) Sending the message that launched a transformation (12:25 [https://www.youtube.com/watch?v=yaG70VotukE&t=745s]) The two-pronged approach: synchronous and asynchronous learning (17:29 [https://www.youtube.com/watch?v=yaG70VotukE&t=1049s]) Encouraging experimentation and creative exploration (18:41 [https://www.youtube.com/watch?v=yaG70VotukE&t=1121s]) How AI enables designers to move beyond MVP thinking (22:00 [https://www.youtube.com/watch?v=yaG70VotukE&t=1320s]) Quick summary of the two-pronged approach (24:43 [https://www.youtube.com/watch?v=yaG70VotukE&t=1483s]) Measuring AI adoption (33:48 [https://www.youtube.com/watch?v=yaG70VotukE&t=2028s]) Creating a centralized AI knowledge center (35:58 [https://www.youtube.com/watch?v=yaG70VotukE&t=2158s]) Building an MCP server to demonstrate AI’s potential (44:08 [https://www.youtube.com/watch?v=yaG70VotukE&t=2648s]) Why technical understanding is crucial for non-technical roles (46:01 [https://www.youtube.com/watch?v=yaG70VotukE&t=2761s]) Final thoughts — Tools referenced: • Cursor: https://cursor.com/ [https://cursor.com/] • Bolt.new: https://bolt.new/ [https://bolt.new/] • Claude: https://claude.ai/ [https://claude.ai/] • ChatGPT: https://chat.openai.com/ [https://chat.openai.com/] • Midjourney: https://www.midjourney.com/ [https://www.midjourney.com/] • Gemini: https://gemini.google.com/ [https://gemini.google.com/] — Other references: • Pendo: https://www.pendo.io/ [https://www.pendo.io/] • Confluence: https://www.atlassian.com/software/confluence [https://www.atlassian.com/software/confluence] • Slack: https://slack.com/ [https://slack.com/] — Where to find Brian Greenbaum: LinkedIn: https://www.linkedin.com/in/briangreenbaum/ [https://www.linkedin.com/in/briangreenbaum/] — Where to find Claire Vo: ChatPRD: https://www.chatprd.ai/ [https://www.chatprd.ai/] Website: https://clairevo.com/ [https://clairevo.com/] LinkedIn: https://www.linkedin.com/in/clairevo/ [https://www.linkedin.com/in/clairevo/] X: https://x.com/clairevo [https://x.com/clairevo] — Production and marketing by https://penname.co/ [https://penname.co/]. For inquiries about sponsoring the podcast, email jordan@penname.co.

Highlights

Brian Greenbaum, a senior product designer at Pendo, shares how a personal experience during paternity leave led to a transformative AI initiative within his organization. What began as an individual exploration of AI coding tools quickly evolved into a structured, company-wide effort to integrate artificial intelligence across product teams.
04:00
Created a working prototype in a couple of hours using Cursor
10:26
Many people on parental leave are using AI tools like Cursor and are likely to return 'AI pilled'
12:26
Product people must develop iterative AI use and data skills to stay relevant
17:31
Give wacky instructions to AI to make the experience fun and mind-expanding for designers and PMs.
18:55
AI makes it easier to generate visual and interactive elements that were previously costly or difficult to produce
32:26
Documented AI tool guidance creates a snowball effect for organizational change
33:48
Synchronous meetings, asynchronous Slack channels, and OKRs are key to driving AI transformation.
43:42
Letting peers experience ideas through AI tools can influence the product roadmap.
44:08
Knowing HTML and CSS empowers designers to leverage AI coding tools effectively

Chapters

Introduction to Brian Greenbaum
00:00
Brian’s paternity leave epiphany that sparked an AI initiative
01:38
Sending the message that launched a transformation
05:00
The two-pronged approach: synchronous and asynchronous learning
12:25
Encouraging experimentation and creative exploration
17:29
How AI enables designers to move beyond MVP thinking
18:41
Quick summary of the two-pronged approach
22:00
Measuring AI adoption
24:43
Creating a centralized AI knowledge center
33:48
Building an MCP server to demonstrate AI’s potential
35:58
Why technical understanding is crucial for non-technical roles
44:08
Final thoughts
46:01

Transcript

Brian Greenbaum: I had tried Cursor for the first time, and what I was able to create just blew me away. I sent a message to my manager, my manager's manager, the CPO. And then a few other folks that I knew were really interested in AI, and I was like, lis...