Supra Insider

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

Peter Walker, Head of Insights at Carta, dives into the changing landscape of product management compensation. He reveals modest salary shifts and a decline in equity compensation since 2022. The conversation explores how AI is reshaping industry roles and altering hiring patterns. Peter also discusses the tricky terrain of equity exercise risks and why many employees hesitate to cash in on options. With insights on navigating the competitive job market, Walker's expertise sheds light on the future dynamics of the startup ecosystem.

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Alvaro Morales, CEO and co-founder of Orb, a company revolutionizing modern billing infrastructure with notable customers like Vercel, Perplexity, and Replit. Alvaro shared his journey from being an engineering manager at Asana to launching Orb after encountering challenges with pricing iterations.He also discussed the evolving role of pricing in product strategy and the rise of usage-based and outcome-based pricing models. Additionally, he shared his insights into the psychology behind pricing decisions, the importance of building customer trust, and how Orb's platform enables cross-functional teams to refine pricing with the same speed and efficiency as their product updates.If you're a product, engineering, or finance leader curious about transforming your pricing strategy or building more agile processes, this conversation is packed with actionable insights.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 Alvaro’s experiences at Asana inspired the creation of Orb* The challenges modern teams face with pricing* The psychology of pricing and how customer trust plays a pivotal role* Outcome-based pricing as the “holy grail” and why it’s so difficult to achieve* How Orb helps companies make pricing a dynamic, strategic advantage* Alvaro’s journey with early design partners to refine Orb’s pricing* Key trends in freemium, reverse trials, and usage-based pricing* And much more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Alvaro Morales: https://www.linkedin.com/in/alvaro-morales/* Alvaro Morales X: https://x.com/alvaromorales* Orb: https://www.withorb.com/* Alvaro Morales Email: alvaro@withorb.com* 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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Teresa Torres, author of Continuous Discovery Habits, to explore the role of AI in modern product discovery. Teresa shared why customer empathy remains irreplaceable, the common pitfalls teams face when misusing AI in research, and practical strategies for integrating AI effectively—without losing sight of the human touch.She also offered her insights on how AI can empower product teams to build skills, enhance customer interviews, and streamline discovery workflows, all while staying firmly rooted in authentic customer understanding. If you're passionate about truly knowing your customers and using AI as a tool—not a crutch—this episode is brimming with valuable takeaways!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:* Why AI can enhance but never replace human-driven customer research* The pitfalls of relying on synthetic users and autogenerated personas* How to use AI as a “team member” to synthesize interviews and uncover insights* Importance to building curiosity and empathy into product teams* Practical use cases for AI in discovery, including feedback analysis and research repositories* Exciting experiments Teresa is running with AI to help PMs hone their interviewing skills* The importance of owning your audience and the challenges of modern social media platforms* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Teresa Torres: https://www.linkedin.com/in/teresatorres/* Teresa Torres X: https://x.com/ttorres* Product Talk: https://www.producttalk.org/* Product Talk Daily Substack: https://producttalkdaily.substack.com/* Product Talk Videos: https://videos.producttalk.org/* 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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Tal Raviv, an experienced product manager and AI enthusiast, to explore the intersection of AI and productivity in product management. Tal shares insights from his career, including his time as the first PM at Riverside and his work building generative AI features.We dove deep into the myths surrounding AI's role in product management, the power of context when working with tools like Claude and ChatGPT, and practical use cases for both co-pilots and agents. Tal also shared tips on creating a personal productivity system and how product managers can use AI to become more effective and impactful in their roles. Whether you're new to AI or looking to level up your approach, this episode has something for you.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:* The myths surrounding AI in product management and its potential to reshape workflows* The distinction between AI co-pilots and agents and their applications in work* Practical use cases for leveraging AI tools like Claude to enhance productivity* Building a personal productivity system to manage tasks, time, and stress effectively* How foundational productivity skills amplify the effectiveness of AI tools* Exploring the balance between offloading routine tasks and improving strategic thinking* Insights into career transitions, solopreneurship, and redefining personal success* Predictions for the future of AI's role in product management* Inspiration and practical advice for professionals at all levels* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Tal Raviv: https://www.linkedin.com/in/talsraviv/* Tal’s Maven Course: https://maven.com/tal-raviv/product-manager-productivity-system* Claude: https://www.claude.ai* Reflect: https://reflect.app/* Granola: https://www.granola.ai/* Grain: https://grain.com/* 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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Sunil (Sunny) Chaudhary, a former product leader turned recruitment director at Riviera Partners, one of the top recruiting firms in tech. Sunny shares his journey from leading product teams to helping companies hire the right product leaders, offering a unique perspective from both sides of the hiring table.In this episode, Sunny also dives deep into how the product leadership market is evolving, from the rising demand for AI expertise to the increasing focus on doers over managers. He shares actionable advice for candidates on standing out in competitive hiring processes, breaking into AI roles, and navigating compensation trends for super senior ICs and managers.Whether you’re a product leader looking to land your next role or a founder hiring for a critical product position, Sunny’s insights into market trends, recruiter dynamics, and interview best practices are invaluable.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 hiring priorities are changing and the rise of specialized product roles* What companies are looking for in AI product leaders and how candidates without AI experience can position themselves* Key strategies and traits of the top 1% of candidates in product leadership* How senior IC roles are catching up with or surpassing managerial positions in pay and equity* The current state of workplace flexibility and its impact on hiring* And more!If you’d like to watch the video of our conversation, you can catch that on YouTube:Links:* Sunil (Sunny) Chaudhary: https://www.linkedin.com/in/sunilchaudhary/* 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

Gibson Biddle, former VP of Product at Netflix and Chief Product Officer at Chegg, shares insights on transitioning from full-time roles to fractional leadership. He discusses redefining success and his innovative approach to balancing impact and flexibility. Biddle highlights the importance of structured feedback and his strategies for engaging audiences effectively. He also dives into building community through workshops and storytelling, emphasizing personal growth and continuous learning in the dynamic landscape of product leadership.

In a captivating discussion, salary negotiation coach Josh Doody shares his expertise on securing fair compensation. He advocates for changing jobs every few years to boost earnings and reveals the pitfalls of prematurely disclosing salary expectations. Doody emphasizes the art of negotiating both within a current company and for new roles, ensuring listeners understand market dynamics. Highlighting strategies like leveraging competing offers, he inspires confidence in tackling salary discussions, making this a valuable resource for anyone looking to enhance their career.

John Cutler, a product management expert and writer, teams up with Joshua Herzig-Marx, a seasoned product leader, to delve into the challenging job market for product leaders. They explore the factors behind prolonged job searches, including the flattening of product organizations and the rise of super IC PMs. The conversation highlights how AI is reshaping product leadership dynamics and offers valuable advice for those navigating career transitions. Together, they predict significant changes in the landscape of product management over the next decade.

Ben Sprecher, CPO at bookend.ai and a veteran in the AI field, shares insights from his 24-year journey, including founding a company acquired by Google. He discusses his early bets on AI's potential and highlights the 'AI demo trap'—a common pitfall where companies rush to showcase products without substance. Ben offers frameworks for assessing AI projects, shifting from defensive to offensive strategies, and turning AI concepts into real customer value, making it essential listening for founders and product managers.