Chris Gomes set out to hire four AI product managers. Seven months later, his biggest lesson was not about AI at all. In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Chris Gomes, VP of Product at Conveyor, the Series B startup that automates responses to security questionnaires and RFPs. Chris walks through the seven months he spent hiring four AI PMs, why he spent so long defining what an “AI product manager” even means, and the realization that culture fit, not AI skill, was the thing that actually predicted success. They explore how he rebuilt a stalled interview process by pulling the most important screens to the front, the MOC framework he uses to map each interview step to specific competencies, his case for work trials and customer role-plays, how he treats references and back-channels, and why the gut-level question of whether you’d enjoy working with someone deserves more weight than most rubrics give it. If you’re a hiring manager trying to run a tighter, higher-signal process, a founder thinking about your first product hires, or a PM preparing for interviews and wondering what teams are really evaluating, this episode is for you. All episodes of the podcast are also available on Spotify, Apple and YouTube. New to the pod? Subscribe below to get the next episode in your inbox 👇 Want company-specific interview intel? If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below. Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50 In this episode, we covered the following topics: * (03:47) Chris sets the scene: hiring four AI PMs at Conveyor after their Series B * (05:09) The big realization: culture fit matters far more than AI skills, and most of the AI part is teachable * (06:42) How to actually interview for culture by naming what’s genuinely different about yours * (08:25) Conveyor’s specifics: hungry, humble, smart, plus customer discovery and the honesty-versus-decisiveness balance * (12:33) Why they were whiffing, and bringing in recruiter Chris Lee to fix the process * (13:35) Treating hiring like a product: pull the most important screens forward and de-risk the riskiest parts first * (19:44) Respecting candidates’ time by cutting performative steps that generate mixed signal * (21:49) Closing with transparency: walking finalists through the board deck, good, bad, and ugly * (24:16) The work-trial dream, and a more interactive take-home as a middle ground * (30:27) Their take-home plus a live customer role-play that proved the most predictive step * (35:56) The MOC framework: mission, outcomes, and stack-ranked competencies mapped to each step * (40:23) Taking references seriously, the “Who” method, and where back-channels actually help * (51:02) The vibes question: can you capture whether you’d enjoy working with someone * (59:30) Meeting finalists in person, even for remote roles, and the jerk-to-the-waiter signal * (1:03:38) How much to share with candidates upfront, and valuing thinking on your feet * (1:11:08) Evaluating AI depth without chasing the flavor of the day, plus what they under-tested * (1:18:53) Gratitude Corner: Chris thanks Chris Lee, Sydney, and Chas * And more! Links: * Chris Gomes on hiring AI PMs: * https://www.linkedin.com/posts/gomeschris_over-the-past-7-months-ive-hired-4-product-share-7401947584958787584-O9Um/ * https://www.linkedin.com/posts/gomeschris_takeaway-2-from-hiring-four-pms-w-ai-depth-share-7440043809100484608-ziTH/ * Conveyor: https://www.conveyor.com/ * Chris Lee: https://www.linkedin.com/in/thechrislee/ * Sydney Shea: https://www.linkedin.com/in/sydneyfshea/ * Chas Ballew: https://www.linkedin.com/in/chasballew/ * Chris Gomes: https://www.linkedin.com/in/gomeschris/ * Marc: https://www.linkedin.com/in/marcbaselga/ * Ben: https://www.linkedin.com/in/benerez/ If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed: To support the podcast, please check out the links below: * Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here). * Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com
