How to Stay Current, Get Hired, and Last in AI

In this episode, I sit down in person with three of my closest friends in The Skip Community, each of whom took on an AI role recently: Dana Ingraham, who runs core product at Harvey after seven years at Airbnb, Hemal Shah, who moved from OpenAI to Google Cloud, and Jiaona "JZ" Zhang, CPO of Laurel and formerly of Webflow. We get into the common product career advice they push back on, from needing to be “AI-pilled” to land an AI job, to following everything to stay current, to judging a company by its valuation, and what they do instead. We also talk about how they manage all-consuming jobs with young families at home, and why JZ says AI "literally makes us able to do all the things." Key topics: • Why Dana disagrees that you need to be "AI-pilled" to get an AI job, and what she hires for instead • Hemal's three skills of a great PM today: historian, technologist, and anthropologist • Why curiosity and adapting to change as the traits that matter even more now • Staying current through "people curation" instead of consuming everything • Choosing a company by its data, distribution, people, and willingness to change • Why JZ recommends forward-deployed and AI operations roles over waiting for a PM title • Ruthless prioritization: "What is one thing I would regret not doing with my time right now?" • Why joy, not time management, prevents burnout Timestamps: 00:00 Introduction 04:38 Meet the three leaders who each took on a new AI role 05:22 What they built at home with AI, from college applications to kids' apps 11:33 How do they find the time? 14:24 Why JZ says yes to teaching at Yale and no to almost everything else 16:33 Hemal on why you can't have it all 17:58 Why Dana left Airbnb after seven years for Harvey 20:12 Ruthless prioritization: "What is one thing I would regret not doing?" 22:47 Prioritizing at home versus at work, and whether kids made them better professionals 26:48 Why Dana disagrees that you need to be "AI-pilled" to get an AI job 31:51 Hemal's three skills of a great PM: historian, technologist, anthropologist 33:04 Why curiosity and adapting to change as the traits that matter even more now 35:41 How to stay current: the job itself and Hemal's "people curation" 42:38 JZ on why unique data is the moat at Laurel 45:58 Hemal's playbook: data, distribution, people, and a company willing to change 49:41 JZ's advice: take the forward-deployed or AI operations role, not just the PM title 51:12 Early-career advice: your next job is forward deployed at a startup you've never heard of Brought to you by: • Firecrawl—Gives your AI agents data from the web and beyond—Redeem your SKIP coupon to get 10,000 Firecrawl credits under Settings → Billing → Coupons in the Firecrawl dashboard: https://firecrawl.dev/skip • Stripe Treasury—Bring payments and finances together: https://stripe.com/treasury Referenced: • Adventure Worlds: https://adventureworlds.ai/ • Airbnb: https://www.airbnb.com/ • Angela Duckworth: https://angeladuckworth.com/ • Anthropic: https://www.anthropic.com/ • Claude Code: https://www.claude.com/product/claude-code • Decagon: https://decagon.ai/ • Google: https://www.google.com/ • Google Cloud: https://cloud.google.com/ • Grit: https://www.angeladuckworth.com/grit • Harvey: https://www.harvey.ai/ • Inside PM at Gemini: https://theskip.substack.com/p/inside-gemini-how-google-runs-product • Laurel: https://laurel.ai/ • Midjourney: https://www.midjourney.com/ • OpenAI: https://openai.com/ • OpenClaw: https://openclaw.ai/ • Reforge: https://www.reforge.com/ • Sierra: https://sierra.ai/ • SNOO: https://www.happiestbaby.com/products/snoo-smart-sleeper • Stanford University: https://www.stanford.edu/ • Tulsee Doshi: https://linkedin.com/in/tulsee-doshi/ • Webflow: https://webflow.com/ • Yale University: https://www.yale.edu/ Where to find Nikhyl: • Twitter/X: https://x.com/nikhyl • LinkedIn: https://linkedin.com/in/nikhyl/ Where to find Dana: • LinkedIn: https://linkedin.com/in/danabressler/ Where to find Hemal: • Twitter/X: https://x.com/hemal • LinkedIn: https://linkedin.com/in/hemaljshah/ Where to find JZ: • Twitter/X: https://x.com/jiaonazhang • LinkedIn: https://linkedin.com/in/jiaona/ Join The Skip: • Skip Coach: https://skip.coach/ • Skip Community: https://skip.community/ Find The Skip: • Website: https://www.skip.community/ • Substack: https://theskip.substack.com/ • YouTube: https://www.youtube.com/@theskippodcast • Spotify: https://open.spotify.com/show/4oT2rxMsRP64h9NXuA11DJ • Apple Podcasts: https://podcasts.apple.com/us/podcast/the-skip-podcast/id1663529202 Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. Access exclusive sessions from 100+ top product leaders at http://skip.coach. If you're interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community