What does it actually take to move an entire company from handwriting PRDs to shipping features with agents in two years?
In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Alex Meyers, Principal Product Manager at Gusto, to trace how the company became AI-native from the inside. Alex shares how his own quiet tool use turned into a C-suite demo, why that demo made clear that you cannot simply mandate “be AI native,” and how PM AI hackathons became the ritual that moved the org forward.
They explore why dedicated, uninterrupted build time beats an hour here and there, why the ritual has to recur as the tools keep changing, how roughly three-quarters of the PM org now merges pull requests, and where Alex thinks the work is heading as loops and goals let PMs spend more time on customers and taste.
If you’re a product leader trying to raise your team’s AI fluency, a founder deciding how much structure to put around learning, or an operator wondering what the PM role becomes when agents handle the busywork, this episode is for you.
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In this episode, we covered the following topics:
* (00:30) Alex on Gusto’s two-year shift from few AI subscriptions to fully AI-native
* (03:57) How adoption spread: his own tool use, the CPO noticing, and early show-and-tell
* (07:06) The pivotal C-suite Cursor demo and the aha that you must create time and structure
* (09:50) The secret sauce: long uninterrupted build blocks over an hour a day
* (12:41) The two big levers: shared access with connected data, plus dedicated space and resources
* (15:00) Why hackathons have to recur as tools change, from prompting to loops
* (22:49) The confidence jump: 11% of PMs to 83% around the hackathons
* (24:44) Working on the business versus in the business, with outputs that ship to customers
* (31:09) The spicy topic: PMs merging PRs, and starting small with tight review gates
* (38:54) A Cursor case study where a PM shipped a feature end to end
* (42:37) Loops versus cron jobs, and the shift to think-and-judge tasks
* (47:15) The CEO founder-mode analogy: humans infusing taste into their own systems
* (52:40) The emerging skill of killing loops, notifications, and artifacts that no longer serve you
* (57:32) Where to find Alex and how listeners can help
* (58:47) Gratitude Corner: Alex thanks his eBay and Gusto bosses, and Marc
* And more!
Links:
* Claire Vo: https://www.linkedin.com/in/clairevo/
* Boris Cherny: https://www.linkedin.com/in/bcherny/
* Peter Steinberger: https://www.linkedin.com/in/steipete/
* Bradford Shellhammer: https://www.linkedin.com/in/bradfordshellhammer/
* Cyrus Mansoor: https://www.linkedin.com/in/cyrusmansoor/
* Katya Fuks: https://www.linkedin.com/in/katya-fuks-58b4272/
* Albert Hsu: https://www.linkedin.com/in/alberthsu5/
* Jasper Malcolmson: https://www.linkedin.com/in/jaspermalcolmson/
* Alex Meyers Website: https://www.alexjmeyers.com/
* Alex Meyers: https://www.linkedin.com/in/alexjmeyers/
* Marc: https://www.linkedin.com/in/marcbaselga/
* Ben: https://www.linkedin.com/in/benerez/
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