In this episode, three leaders who recently took on AI roles break down their job search: Anthony Maggio, who left Airtable after five and a half years to become CPO at Runway, Gadi Ben-Zvi, who leads AI platform and products at Eli Lilly, and Chandra Raghavan, a principal PM on Search AI at Google. This is the third conversation in our job-search series, where about every 100 days I check in with executives who just landed new roles to see what has changed. We get into why Anthony passed on the frontier labs for a 200-person company, why Gadi joined Eli Lilly, a company willing to spend years on its AI bets, and why Chandra says choosing between a startup and big tech is “a false dichotomy.”
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Key topics:
• The interview questions that test AI judgment, starting with "Where did it fail?"
• Why a side project of your own became the credential
• How to avoid becoming "the person who tried ChatGPT in 2022"
• Why a senior IC role on Google Search AI feels more like a startup than big tech
• How to tell if a company has a real edge in AI
• What hasn’t changed in senior PM interviews, and the new baseline
• What to stop highlighting: managing through layers and cross-functional coordination
• How candidates stand out now: auditing the product and prototyping fixes after a first conversation
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Timestamps:
00:00 Introduction
02:58 Meet the three leaders who just landed AI roles at Lilly, Runway, and Google
09:19 Anthony's search criteria: proximity to the frontier, talent density, and fit
14:30 How research breakthroughs become products at Runway
15:57 Why a 200-person company beat the big labs
19:32 What Eli Lilly built with 150 years of data, and why the bet will last
23:09 Optimizing for 2026 Chandra, not 2016 Chandra
26:05 Startup-style ownership at scale: Chandra's "false dichotomy"
29:08 What surprised them about interviews
33:44 How to speak credibly about agents when your job doesn't build them
39:44 What Eli Lilly wanted from a product leader with no pharma background
41:20 The questions interviewers are asking about AI
43:10 Why continuous experiments beat one big project
48:31 What past experience still counts, and what to stop highlighting
50:31 How candidates stand out now: auditing the product and prototyping fixes after a first conversation
52:58 Finding a company's real edge: proprietary data, domain expertise, feedback loops
56:23 How Google Search moves like a startup, and why you onboard yourself
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Brought to you by:
• Chargebee—Billing and monetization infrastructure for the AI era
• Stripe Treasury—Bring payments and finances together
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Referenced:
• 10 Job Search Rules That Just Broke
• Airtable
• Airtable Omni and Field Agents
• Anthropic
• ChatGPT
• Claude
• Eli Lilly
• Google
• Google AI Mode
• Google AI Overviews
• Google Photos
• Meta
• OpenAI
• Runway
• Runway Solaris
• Three Job Searches, Three AI Roles
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Where to find Nikhyl:
• Twitter/X
• LinkedIn
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Where to find Anthony:
• Twitter/X
• LinkedIn
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Where to find Gadi:
• LinkedIn
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Where to find Chandra:
• LinkedIn
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Join The Skip:
• Skip Coach
• Skip Community
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Find The Skip:
• Website
• Substack
• YouTube
• Spotify
• Apple Podcasts
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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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