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How I AIHow one designer led an AI revolution at Pendo: The paternity leave epiphany | Brian Greenbaum
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At a glance
WHAT IT’S REALLY ABOUT
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).
- He then drove adoption with a two-pronged model: recurring synchronous learning sessions with live exercises, plus an asynchronous Slack channel for “radical many-to-many sharing.”
- To make AI usage safe and scalable, the team measured sentiment and awareness, then built a centralized AI Knowledge Center that clarified approved tools, data rules, and procurement pathways.
- Brian also demonstrates how individual experimentation can influence company roadmap—e.g., building a prototype MCP server to show how agents could query Pendo data and generate dashboards.
IDEAS WORTH REMEMBERING
5 ideasA single concrete “I built this” moment can ignite organizational change.
Brian’s fast Cursor-built prototype created undeniable proof, making his leadership outreach compelling and actionable rather than hypothetical.
Position AI adoption as both productivity and market leadership.
He framed the initiative around internal leverage (do more, better decisions) and external credibility (Pendo as a thought leader for customers undergoing the same shift).
Adoption requires both calendar time and a sharing surface.
Bi-weekly sessions create protected time for hands-on practice, while a public Slack channel sustains momentum through continuous peer examples and experimentation.
Make sessions interactive to reveal how AI really behaves.
Having everyone run the same Bolt.new prompt exposed variability, failures, and debugging realities—building practical confidence instead of “AI theater.”},{
Use playful experimentation to break “MVP-only” thinking.
Encouraging wild iterations (themes, gamification, media) helps PMs/designers rebuild the muscle of imagining “magic” experiences now feasible with AI.
WORDS WORTH SAVING
5 quotes“I think we really need to uplevel the skill of our entire product organization, not just designers, but also PMs.”
— Brian Greenbaum
“There’s no playbook for how to learn this stuff… the technology’s evolving so fast.”
— Brian Greenbaum
“If you don’t make the time for it, you’re never gonna learn it, and at some point you’re gonna get behind.”
— Brian Greenbaum
“We’ve lost our muscle for asking for the magic thing… now our bar can just be so much higher.”
— Claire Vo
“One of my most popular sessions… was called ‘WTF is MCP?’”
— Brian Greenbaum
High quality AI-generated summary created from speaker-labeled transcript.
