Three Job Searches, Three AI Roles: What Actually Worked
The Skip Podcast
Julia's transition: Pinterest to OpenAI
Julia recounts nine years at Pinterest, six months off, and deciding to pursue an IC role focused on retention at OpenAI.
Most job search advice comes from people still in the thick of it—anxious, second-guessing, pattern-matching off too little data. This episode is different. We sat down with three product leaders who recently landed roles at Netflix, OpenAI, and Abridge, and did a full postmortem. What they shared upends a lot of conventional wisdom: the spray-and-pray pipeline doesn't work, your AI credentials matter less than you think, and the relationships that land jobs are often years in the making.
Key topics
• Why you need curiosity, not experience
• The "AI hungry" mindset: searching for environments that match your learning goals, not just your resume
• Why the best job search intelligence comes from people who just landed, not people still looking
• Why prototypes are now table stakes in take-homes
• How Janie built a shortlist of 5–10 companies in a week of 50–60 conversations
• Why Ben's Netflix role traces back to a cold application seven years ago
• What OpenAI's interview process actually looks like—and why it's less about the past than you expect
• Why most AI-native jobs aren't posted, and how to land them
• How to use investor attention as a proxy for company quality
• Why Ben's early interview mistake (not enough AI mindset) became the fuel for his take-home
Brought to you by
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Timestamps
(00:00) How to prove your AI credentials
(04:42) Introducing the three product leaders
(06:00) Ben Dreier: from DoorDash to Netflix, the "AI hungry" move
(08:18) Julia Roberts: nine years at Pinterest, six months off, then OpenAI
(12:46) Janie Lee: going all-in on AI native at Abridge
(15:26) How to build a shortlist: 50–60 conversations in a week
(18:10) Ben's process: VC signals and insider conversations over job boards
(21:45) Cold outreach that actually works
(23:51) Ben: how curiosity, not networking, built his network
(25:14) Julia's different path: cold applies, inbound, and exec recruiters
(27:06) What exec recruiters are actually useful for
(30:30) Ben's Netflix backstory — tracing back to a cold apply seven years ago
(34:06) Staying connected with recruiters, coworkers, and people who said no
(41:10) What the OpenAI interview process actually looks like
(44:55) Authentic storytelling
(46:40) The Netflix take-home: how mid-process feedback became a turning point
(51:40) Janie: how to ace take-homes by using AI
(57:52) Julia’s final takeaway: know what you want before you search
(59:03) Ben’s final takeaway: follow the fun and genuine curiosity
(59:56) Janie’s final takeaway: high agency, high effort, put yourself in their shoes
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 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
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