Supra Insider

• #64: How top companies evaluate PM candidates in 2025 | Nickey Skarstad (Duolingo), Stephanie J. Neill (Stripe), and Chantal Cox (LTK)

  If you’re navigating today’s brutally competitive PM job market and wondering what “good” looks like, this episode will become your playbook. In this episode, Ben moderates a candid panel with three veteran product hiring managers:Nickey Skarstad – Director of Product, Duolingo (now leading Duolingo Math)Stephanie J. Neill – Head of Product, Stripe TaxChantal Cox – Director of Product, LTK (LiketoKnow.it creator platform)Together, they reverse-engineer every stage of their 2025 hiring funnels—from 30-second resume scans to offer debriefs—and spell out the signals that turn an applicant into a hire. You’ll hear why product-sense interviews have moved to earlier in the process, how AI prototypes are becoming table-stakes, and the red flags (LLM-generated answers, recycled stories etc.) that get instant no-hires. Whether you’re an aspiring PM or a manager revamping your own process, you’ll leave with concrete, immediately applicable tactics for landing—or giving—an offer.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 👇To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting July 15th.* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.In this episode, we covered the following topics:* (01:40) Guest intros: Nickey (Duolingo), Stephanie (Stripe), Chantal (LTK).* (08:00) Chantal details LTK’s funnel—recruiter screen, hiring-manager call, AI feature exercise, leadership loop.* (11:30) Stephanie explains Stripe’s flow and why Product Sense now precedes the full loop.* (13:20) Nickey walks through Duolingo’s four rounds and the new interactive prototype requirement.* (17:50) What wins a résumé review: tight one-page metrics, LinkedIn consistency, warm referrals.* (24:40) Hiring-manager screens: confirming skill fit, probing AI curiosity, expecting candidates to have used the product.* (31:00) Offer debriefs—looking for “spikes” in key areas, guarding against bias, zero tolerance for failed rounds at Duolingo.* (43:40) How candidates should and should not use Gen-AI; interview-prep bots, friction logs, lightweight prototypes.* (50:20) Early-career advice: move internally, start in customer-facing roles, ship side-project AI apps, network before you need it.* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Nickey Skarstad: https://www.linkedin.com/in/nickeyskarstad/* Stephanie J. Neill: https://www.linkedin.com/in/stephanieneill/* Chantal Cox: https://www.linkedin.com/in/chantalcoxsf/* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: 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

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• #63: How PMs can bring predictability to AI products | Aman Khan (Head of Product @ Arize AI, ex-Spotify, ex-Apple)

  If you’ve ever launched an AI feature and later realized it wasn’t quite ready—or struggled to define what “quality” even looks like in an AI product—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Aman Khan, Head of Product of Arize AI and a leading voice in AI product evaluation. Aman has helped dozens of teams—from scrappy startups to massive consumer platforms—build systematic approaches for evaluating LLM-powered features. Together, they explore the dangers of “vibe coding” your way to production, how to define and operationalize evals across different layers of your product, and why even “good” outputs can still lead to bad outcomes without proper measurement.Whether you’re a PM under pressure to ship AI features fast, or a product leader figuring out how to instill quality and reliability into your development process, this conversation is packed with frameworks, analogies (like self-driving cars), and hard-won lessons you can use to build smarter and ship more confidently.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 👇To support the podcast, please check out the links below:* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN. Aman’s course is part of the partnership 🚀* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting July 15th.In this episode, we covered the following topics:* (00:00) The danger of launching AI features without proper evaluation—and why trust is hard to rebuild* (04:12) “Vibe coding” explained: when teams ship based on gut feel instead of structured validation* (09:07) Real-world example: a travel chatbot gets great engagement—until users start jailbreaking it* (15:36) Defining “good enough”: how to set AI quality metrics across tone, latency, hallucinations, and risk* (19:58) What PMs can learn from self-driving car evals—and how to build iterative test sets for reliability* (23:04) How LLM-as-a-judge works: using one model to grade another, and when to rely on human labels* (34:14) Spotting dangerous “false positives”: when outputs seem right but come from flawed reasoning* (42:22) What to do when your evals say “good” but the business metrics drop—and who’s responsible* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Aman Khan Website: http://amank.ai* Aman Khan: https://www.linkedin.com/in/amanberkeley/* Aman Khan X: https://x.com/_amankhan* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: 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

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• #62: Why the future belongs to spiky PMs who use AI to magnify their strengths | Hilary Gridley (Head of Core Product @ WHOOP)

  What actually sets you apart in a world where AI can do more and more of your job? In this episode, Marc and Ben are joined by Hilary Gridley—Head of Core Product at WHOOP and instructor of the Maven course How to Be a Supermanager with AI—to unpack how great product leaders can use AI to magnify their strengths instead of dulling them.Hilary breaks down her approach to time allocation, sharing how she dissects messy, ambiguous work into its component parts and uses AI as a thinking partner—not a crutch. They explore how to identify high-leverage tasks, when investing time is essential for clarity, and why doing something the hard way is sometimes the point. The conversation also touches on how PMs can design their roles around their superpowers, what good taste really means in product, and how managers can help their team grow by doubling down on what makes them exceptional.If you're trying to become more intentional with how you spend your time, use AI more thoughtfully, or lead a team of PMs in this new era—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 👇To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.In this episode, we covered the following topics:* (00:00) Hilary’s approach to identifying and doubling down on her spikes as a product leader—and how AI helps magnify them.* (04:00) How she breaks down ambiguous product work into sub-skills to better allocate time and energy.* (11:30) The tradeoff between leverage and clarity—and why doing something the hard way can be the right call.* (17:00) Frameworks Hilary uses to decide when to delegate, when to coach, and when to go deep herself.* (22:00) How she uses AI tools like Claude as thinking partners to sharpen ideas and move faster.* (27:00) Why “taste” in product is hard to teach—but essential to develop as a PM.* (32:30) The biggest mistake new managers make when trying to “round out” their team—and how to coach for spikes instead.* (38:00) How to build a team with differentiated strengths that complement each other instead of copying one another.* (44:00) What Hilary learned from teaching 100+ managers in her Maven course on using AI to lead more effectively.* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Hilary Gridley: https://www.linkedin.com/in/hilarygridley/* Hilary’s Substack: https://hils.substack.com/* How to Become a Supermanager with AI: https://maven.com/hilary-gridley/ai-powered-people-management* Hilary’s recent episode on “How I AI” with Claire Vo* Superpowers by SYPartners: https://apps.apple.com/us/app/superpowers-by-sypartners/id1309752471* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: 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

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• #61: How jobs-to-be-done (JTBD) nearly killed our startup | Troy Sultan and Austin Cooley (Co-founders @ Guide)

  If you’ve ever found yourself torn between chasing a long-term product vision and urgently responding to customer demands—or wondered how to strike the right balance between innovation and pragmatism—this episode is for you.In this episode of Supra Insider, Marc and Ben sit down with Troy Sultan and Austin Cooley, co-founders of Guide, to explore how they transformed their entire product philosophy from idealistic "big bets" into rapid, incremental solutions based on direct customer feedback. Over eight years as co-founders, Troy and Austin have navigated the common pitfalls of visionary product building, learning to validate product ideas faster, communicate clearly with customers, and shift their strategy to achieve real, measurable results.Whether you're a founder trying to align your product roadmap with sales insights, a product leader collaborating closely with visionary executives, or simply want to sharpen your ability to translate customer feedback into actionable decisions, you’ll walk away from this conversation with practical insights you can use immediately to build products that customers genuinely love.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 👇To support the podcast, please check out the links below:* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.In this episode, we covered the following topics:* (00:00) Austin and Troy’s journey shifting from building bloated, overly idealistic products to pragmatic solutions that customers love.* (04:00) How Troy navigated stepping back from product leadership, trusting Austin to fully own the product vision.* (16:00) The pitfalls of being overly attached to frameworks like Jobs-to-be-Done—and why rapidly shipping pragmatic improvements can be more effective.* (25:00) A real-world example of aggressively scoping down features to deliver immediate customer value and accelerate learning.* (34:00) The power of founder-led sales for validating ideas and prioritizing the roadmap based on real customer pull, rather than assumptions.* (45:00) How Guide leverages Slack to create tight feedback loops, strengthen customer relationships, and boost retention through unmatched responsiveness.* (1:12:00) Why consistent, incremental wins ultimately provide more momentum and clarity than chasing long-term idealistic visions.* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube: Links:* Troy Sultan: https://www.linkedin.com/in/troysultan/* Austin Cooley: https://www.linkedin.com/in/adcooley/* Guide: https://www.guide.co/* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.* * If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: 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

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• #60: What PM candidates get wrong about behavioral interviews | Robert Hamilton (PM interview coach, ex-Meta, ex-Google)

  Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Robert Hamilton, executive coach and former Meta and Google PM, to unpack the art and science of behavioral interviews. If you’ve ever struggled with the infamous “leadership and drive” loop or wondered why your best stories aren’t landing, this episode is a must-listen.They explore why behavioral interviews are often harder to prepare for than case-style interviews, how to identify the signal behind the questions, and why storytelling, self-awareness, and emotional authenticity are so critical. Robert shares actionable tactics like the STARLU framework (Situation, Task, Action, Result, Learning, Upgrade) and explains how to build a versatile story bank that reveals your growth mindset and values.Whether you're actively interviewing, coaching others, or just want to improve how you tell your story as a PM, this episode is packed with practical wisdom.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 👇To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.In this episode, we covered the following topics:* Why behavioral interviews feel uncomfortable—and why they’re valuable* How Meta’s “Leadership and Drive” and other behavioral interviews are structured and what they aim to measure* The difference between project storytelling and self-reflective storytelling* How to identify if a question is behavioral and what the interviewer is really asking* The STARLU framework (Situation, Task, Action, Result, Learning, Upgrade) and how to use it* How to build a story bank mapped to core evaluation criteria like ownership, collaboration, scrappiness, and communication* The biggest mistakes candidates make (e.g., lacking authenticity or giving polished but shallow answers)* How to prep for follow-ups and show growth through adversity* Why interviewer calibration is often broken—especially at early-stage companies* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Robert Hamilton: https://www.linkedin.com/in/roberthamiltoncoach/* Acceleration Coach: https://www.accelerationcoach.com/* Marc: https://www.linkedin.com/in/marcbaselga/* Ben: https://www.linkedin.com/in/benerez/To support the podcast, please check out the links below:* Preparing for a PM interview with tech companies like Meta and Google? Check out Ben's course for Product Sense and Analytical Thinking PM interviews (selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥) and his AI Copilot for interview practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Enrollment is now open for the next cohort starting June 17th.* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.* If you enjoyed this conversation, please share it with a friend or colleague 👇Also, if you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:And here are some less recent favorites: 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

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