Supra Insider

• #43: How AI is Impacting the PM - Engineer Relationship | Irene Yu (Founder & CEO @ Skiplevel)

  Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Irene Yu, founder and CEO of Skiplevel, professional training designed to teach PMs how to become more technical without learning to code. In this conversation, they explored Irene’s journey from Amazon engineer to entrepreneur, the communication challenges between PMs and engineers, and how Skiplevel is helping mitigate those challenges. They also discussed the rise of AI features in product development, exploring how PMs can handle edge cases, learn critical AI concepts, and avoid the dreaded "demo trap." Irene also revealed how she used AI to build a personalized therapist and life coach. This episode is packed with valuable takeaways for PMs, engineers, and product leaders looking to level up their collaboration and technical skills.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 the standalone AI Copilot for practice. Supra Insider listeners get 10% off the course with promo code “suprainsider”. Upcoming cohorts: February 4-16, March 4-16.* Want to connect with product leaders like you? Check out Supra, an invite-only community with 350+ product leaders. You'll get matched with a group of 6-8 carefully vetted individuals and participate in a monthly session facilitated by a world-class coach. Last year, members reported solving their top product challenges 3x faster through these sessions. Plus, tap into our vibrant Slack community for "behind closed doors" topics, join exclusive speaker events with industry pioneers, and connect at intimate roundtables and in-person meetups.In this episode, we covered the following topics:* Irene’s motivation for founding Skip Level and her experiences onboarding PMs at Amazon* The communication breakdowns that often occur between PMs and engineers* Why technical onboarding is crucial for effective product teams* Irene's FAIR framework for approaching technical discussions with engineering teams (Feasibility, Alternate Solutions, Impact, Risk Mitigation)* The rise of AI features in product development and their implications on PM responsibilities* Fun insights into using AI for personal growth, including personalized therapy and coaching* And much more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Irene Yu: https://www.linkedin.com/in/iamireneyu/* Skiplevel: https://www.skiplevel.co/* Ben: https://www.linkedin.com/in/benerez/* Marc: https://www.linkedin.com/in/marcbaselga/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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• #42: How AI is changing the way product teams work | Tal Raviv & Joshua Herzig-Marx

  Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Tal Raviv and Joshua Herzig-Marx to explore AI's seismic impact on product development. This conversation unpacks how revolutionary tools like Replit and Vercel v0 are democratizing prototyping and reshaping traditional roles across design, engineering, and product management.Delving beyond surface-level observations, our guests share provocative insights on AI agents' role in reshaping workplace dynamics and envision the emergence of AI-native enterprises. From reimagining established workflows to envisioning AI-first companies, this episode delivers crucial insights for anyone building products in the AI era.All episodes of the podcast are also available on Spotify, Apple and YouTube (video).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, Google, Microsoft, and OpenAI? Check out Ben's Maven bootcamp for Product Sense and Analytical Thinking PM interviews. Supra Insider listeners get 10% off with promo code “suprainsider”. The next cohorts open for enrollment are February 4-16 and March 4-16.* Want to connect with product leaders like you? Check out Supra, an invite-only community with 350+ product leaders. You'll get matched with a group of 6-8 carefully vetted individuals and participate in a monthly session facilitated by a world-class coach. Last year, members reported solving their top product challenges 3x faster through these sessions. Plus, tap into our vibrant Slack community for "behind closed doors" topics, join exclusive speaker events with industry pioneers, and connect at intimate roundtables and in-person meetups.In this episode, we covered the following topics:* How tools like Replit, Vercel v0 are changing the prototyping process* The evolving roles of designers, engineers, and product managers in an AI-driven world* The challenges of integrating AI into legacy systems vs. building AI-native businesses* Why leveraging AI tools is less about magic and more about mastering strategy* The rise of AI agents and their potential to revolutionize decision-making and automation* Balancing creativity, vision, and taste in the age of generative AI* The future of work and how product managers can thrive in a world of infinite leverage* And much more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* AI’s Uneven Arrival: https://stratechery.com/2025/ais-uneven-arrival/* Joshua Herzig-Marx: https://www.linkedin.com/in/joshuaherzigmarx/* Tal Raviv: https://maven.com/tal-raviv/product-manager-productivity-system * Ben: https://www.linkedin.com/in/benerez/* Marc: https://www.linkedin.com/in/marcbaselga/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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• #41: Reflections from 40 episodes and plans for 2025 | Ben Erez & Marc Baselga

  Welcome to another episode of Supra Insider. This time, Marc and Ben take a moment to reflect on their journey after reaching 40 episodes. They share their evolution - from starting the podcast as a fun experiment to crafting the art of genuine conversation that defines their podcast format today.The conversation flows naturally into their aspirations for the new year, exploring exciting trends like AI-powered prototyping and the changing landscape of IC career paths, while sharing practical wisdom on setting expectations and building momentum in both work and life.This episode is packed with actionable insights for anyone looking to refine their workflows, explore new opportunities, or simply hear candid thoughts on how to sustain creative projects over the long haul.All episodes of the podcast are also available on Spotify, Apple and YouTube (video).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, Google, Microsoft, and OpenAI? Check out Ben's Maven bootcamp for Product Sense and Analytical Thinking PM interviews. Supra Insider listeners get 10% off with promo code “suprainsider”. Two cohorts are open for enrollment: February 4-16 and March 4-16.* Want to connect with product leaders like you? Check out Supra, an invite-only community with 350+ product leaders. You'll get matched with a group of 6-8 carefully vetted individuals and participate in a monthly session facilitated by a world-class coach. Last year, members reported solving their top product challenges 3x faster through these sessions. Plus, tap into our vibrant Slack community for "behind closed doors" topics, join exclusive speaker events with industry pioneers, and connect at intimate roundtables and in-person meetups.In this episode, we covered the following topics:* Reflections on the first 40 episodes: lessons learned and favorite moments* Evolving the podcast from an interview format to conversational storytelling* Productivity unlocks, including using AI tools, dictation, and time-blocking* Personal growth: reframing problems, making tough decisions, and simplifying workflows* Trends we're excited about: AI-powered prototyping, PM productivity, and IC career paths* Goals for the new year, including scaling personal projects and refining focus* And much more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Ben: https://www.linkedin.com/in/benerez/* Marc: https://www.linkedin.com/in/marcbaselga/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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• #40: How Pie Insurance Implemented the Product Operating Model | Brenton Sellati (VP of Product @ Pie Insurance)

  Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Brenton Sellati, VP of Product at Pie Insurance, and Joshua Herzig-Marx as the honorary co-host for this episode to dive into the transformational journey of implementing the product operating model at Pie Insurance.Brenton shares how he overhauled Pie’s product strategy, slashing 66% of the roadmap to focus on high-ROI initiatives, aligning leadership, and fostering a product-led culture. With insights from Joshua throughout the discussion, the episode explores the challenges and successes of introducing a problem-first mindset, building cross-functional collaboration, and creating a transparent prioritization system.This episode is packed with actionable advice for product leaders and executives looking to drive organizational change and implement sustainable product practices.All episodes of the podcast are also available on Spotify, Apple and YouTube (video).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, Google, Microsoft, and OpenAI? Check out Ben's Maven bootcamp for Product Sense and Analytical Thinking PM interviews. Supra Insider listeners get 10% off with promo code “suprainsider”.* Want to connect with product leaders like you? Check out Supra, an invite-only community with 350+ product leaders. You'll get matched with a group of 6-8 carefully vetted individuals and participate in a monthly session facilitated by a world-class coach. Last year, members reported solving their top product challenges 3x faster through these sessions. Plus, tap into our vibrant Slack community for "behind closed doors" topics, join exclusive speaker events with industry pioneers, and connect at intimate roundtables and in-person meetups.In this episode, we covered the following topics:* How Brenton implemented the product operating model to transform Pie Insurance’s product strategy* The decision-making process behind slashing 66% of the roadmap and refocusing on high-ROI initiatives* The importance of transparency and a data-driven approach to prioritization* Challenges of transitioning to a problem-first mindset and how Pie Insurance’s leadership aligned to support the change* Practical advice for empowering cross-functional teams and building a culture of continuous improvement* Insights on fostering alignment and navigating organizational change* And much more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Brenton Sellati: https://www.linkedin.com/in/brentonsellati/* Joshua Herzig-Marx: https://www.linkedin.com/in/joshuaherzigmarx/* Ben: https://www.linkedin.com/in/benerez/* Marc: https://www.linkedin.com/in/marcbaselga/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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• #39: How PM compensation has changed in the last two years | Peter Walker (Head of Insights @ Carta)

  Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Peter Walker, Head of Insights at Carta. Drawing from Carta's vast database of over 30,000 companies, Peter offers a data-driven analysis of the evolving compensation landscape in 2024.The conversation delves deep into product management compensation, exploring both cash and equity components across different startup stages. Peter shares unique insights into critical industry challenges, including the complexities of equity exercise decisions and the growing emphasis on capital efficiency in startups.The episode tackles pressing questions facing the PM industry today: How are junior PMs navigating the competitive job market? What's driving the surge in fractional roles? How are executive hiring patterns shifting? Peter also illuminates AI's transformative impact across various functions and its implications for the future of work.This thought-provoking discussion offers key insights for founders, product managers, and anyone interested in understanding the current dynamics of the startup ecosystem.All episodes of the podcast are also available on Spotify, Apple and YouTube (video).New to the pod? Subscribe below to get the next episode in your inbox 👇In this episode, we covered the following topics:* How salaries and equity have shifted in 2024* Why only 30% of employees are exercising their options and the factors behind it* Differences in compensation between early-stage and late-stage startups* The evolving hiring landscape: challenges for junior PMs and opportunities for senior ICs* How capital efficiency is redefining startup hiring practices* The rise of fractional roles and their impact on product management* AI’s influence on various functions and its future trajectory in startups* And much more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Peter Walker: https://www.linkedin.com/in/peterjameswalker/* Carta: https://carta.com/* Carta’s salary benchmark tool: https://carta.com/friend/ * Ben: https://www.linkedin.com/in/benerez/* Marc: https://www.linkedin.com/in/marcbaselga/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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