How one designer led an AI revolution at Pendo: The paternity leave epiphany | Brian Greenbaum

ℹ️ EPISODE INFO

Released

December 22, 2025

Duration

47m

Channel

How I AI

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

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: https://ai.dev/ Lovable—Build apps by simply chatting with AI: https://lovable.dev/ *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._

🎤 SPEAKERS

• Brian Greenbaum

  guest

• Claire Vo

  host

🧾 EPISODE SUMMARY

In this episode of How I AI, featuring Brian Greenbaum and Claire Vo, How one designer led an AI revolution at Pendo: The paternity leave epiphany | Brian Greenbaum explores a designer’s playbook for scaling AI adoption across product teams While on paternity leave, Brian tried Cursor, rapidly built a prototype, and sent a decisive Slack message to leaders proposing an AI upskilling initiative across product (design + PM + others).

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