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 questio...
Jun 02, 2025•1 hr 8 min
Welcome to another episode of Supra Insider. This time, Marc sat down with Kyle Ledbetter and Andy Keil , the co-founders of Dreambase—an AI-native toolset built on top of Supabase. Despite not having formal engineering backgrounds, Kyle and Andy have built and launched three fully functional products in just nine months.They unpack their unique zero-to-one process—from jamming on whiteboards to building multimodal prompts, doing bake-offs across V0, Bolt, and Lovable, and validating with real u...
May 26, 2025•1 hr 13 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Mike Curti , a recently hired product leader, and Joshua Herzig-Marx , a trusted advisor to early-stage startups and product teams. Together, they unpack one of the most mission-critical and misunderstood topics in product leadership: hiring. They break down what’s broken in today’s interview processes, especially for product roles and why simply copying Big Tech often leads to poor outcomes. Josh shares lessons f...
May 19, 2025•1 hr 10 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Melissa Perri , author of Escaping the Build Trap and one of the world’s leading product strategy experts. Melissa shares lessons from advising CEOs, founders, and product leaders on how to build strategy that works, scale from VP to CPO, and navigate the often tricky dynamic between founder-CEOs and product leaders. They also explore how AI is shifting product management and why the fundamentals still matter more...
May 12, 2025•1 hr 12 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Troy Sultan , co-founder and CEO of Guide , to unpack the state of job searching and recruiting in the AI era. Troy shares a compelling behind-the-scenes look at what’s really going on inside recruiting teams today—and why the typical candidate experience is often so broken. He also explains how AI and modern tooling are reshaping hiring in real-time, helping teams scale quality and efficiency without sacrificing ...
May 05, 2025•1 hr 5 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Sanket Kavishwar , Director of Product at Relyance AI. Sanket is one of the most active members in Supra’s AI workflows Slack channel, and in this episode, we explore how he’s transforming his company’s product development process with AI prototyping tools like V0. We dive into how Relyance AI shifted from traditional PRDs to problem statements and interactive prototypes, dramatically accelerating iteration speed,...
Apr 28, 2025•1 hr 11 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Will Newton , Principal Product Architect at Amplitude—and one of our most popular past guests—for a follow-up conversation on the fast-evolving world of AI tooling in product design and development. In just a few weeks since our last chat, Amplitude has gone from early AI experimentation to giving Bolt licenses to every designer. Will takes us inside this transition and breaks down how AI is changing design workf...
Apr 21, 2025•1 hr 9 min
Welcome to another episode of Supra Insider. This time, Ben and Marc sat down with Tal Raviv and Colin Matthews for a candid conversation about how AI is reshaping the work and mindset of modern product managers. They unpack insights from Tal’s recent survey on AI prototyping adoption, common challenges for PMs using AI tools, and the importance of learning how to experiment effectively. Colin shares how his approach to evaluating side projects has shifted now that AI accelerates time to build—a...
Apr 14, 2025•1 hr 8 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with John Cutler and Joshua Herzig-Marx for a wide-ranging conversation about how AI is transforming the way product teams build, collaborate, and scale. John shares why he joined a new early-stage startup as Head of Product and how the team is breaking the traditional rules of product development—starting with a platform-first mindset. The conversation explores the rise of highly configurable tools, the new personas e...
Apr 07, 2025•1 hr 9 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Steven Fabre , co-founder and CEO of Liveblocks , a company helping product teams seamlessly build collaborative experiences—now with AI copilots in the mix. In this conversation, Steven shares his journey from being a designer at InVision to leading a developer tools company that’s rethinking collaboration in the AI era. They talk about how Liveblocks is evolving from enabling human-to-human collaboration to supp...
Mar 31, 2025•1 hr 11 min
Welcome to another episode of Supra Insider. This time, Marc sat down with Phil Ou , founder of Blossomer and former product leader at Google, where he led teams across Google Photos, RCS, and YouTube Ads. Phil now helps early-stage B2B founders get their first 1,000 customers—without hiring a sales team. In this episode, they unpack what it really takes to build a repeatable go-to-market engine, the decision to bootstrap vs. raise VC, and the biggest mistakes founders make when thinking about g...
Mar 24, 2025•1 hr 8 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Rodrigo Davies , the product leader shaping Asana’s AI strategy. Rodrigo shares his journey leading AI adoption at Asana, from educating internal teams to building a culture of AI experimentation. We explore how Asana integrates AI into work management, balances AI innovation with enterprise needs, and develops features that deliver real value—not just hype. Rodrigo also talks about how AI is changing the product ...
Mar 17, 2025•1 hr 3 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Randhir Vieira , Chief Product Officer at Omada Health and a Supra facilitator. Randhir has led product teams at companies like Headspace and brings a deep passion for leadership, communication, and the often-overlooked skill of listening. In this episode, we explore why listening is the foundation of strong leadership, how to give feedback that actually lands, and why the best product leaders focus on building ps...
Mar 10, 2025•1 hr 10 min
Welcome to another episode of Supra Insider. This time, Ben and Marc sat down with Jacob Bank from Relay.app to dive into the rapidly evolving world of AI workflows, automation, and agent systems. Prior to founding Relay.app, Jacob was a Director of Product Management at Google, which he joined after Google acquired his former startup, Timeful. Jacob shares his firsthand experience building AI-driven workflows, what he’s learned from experimenting with AI agents, and how PMs should be thinking a...
Mar 03, 2025•1 hr 12 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Will Newton , Principal Product Architect at Amplitude. With years of experience at companies like Gusto and Feather, Will shares insights into how AI is transforming the design world—from prototyping workflows to the evolving roles within product teams. The conversation explores how AI tools are blurring roles between product managers, designers, and engineers while speeding up development cycles. If you're inter...
Feb 24, 2025•1 hr 16 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Colin Matthews , instructor of two popular AI prototyping courses on Maven. Colin shared his insights on the evolving landscape of AI-powered prototyping tools and how product managers can leverage them to build and test more impactful features faster. The discussion explored different categories of AI prototyping tools, when to use them, and how they’re changing the way teams collaborate. Colin also walked us thr...
Feb 17, 2025•1 hr 12 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Yue Zhao , a former product leader at Thumbtack, Instagram, Meta, and Fuzzy, who now thrives as an executive coach and author. Yue shares her story of moving to Barcelona, exploring new career paths, and writing a book that reshaped her outlook on work and leadership. They dive into key topics like navigating career pivots, staying energized through curiosity, and learning to reframe limiting beliefs. Whether you’...
Feb 10, 2025•1 hr 16 min
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, explori...
Feb 03, 2025•1 hr 10 min
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 env...
Jan 27, 2025•1 hr 23 min
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 wi...
Jan 20, 2025•1 hr 17 min
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 Jos...
Jan 13, 2025•1 hr 4 min
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 complexiti...
Jan 06, 2025•51 min
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 pri...
Dec 30, 2024•1 hr 1 min
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...
Dec 16, 2024•48 min
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 pra...
Dec 09, 2024•1 hr 14 min
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 risin...
Nov 25, 2024•52 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Gibson Biddle , former VP of Product at Netflix and Chief Product Officer at Chegg. Gib shares his journey from full-time product leadership to becoming an interim and fractional executive, driven by the desire to live life on his own terms. He discussed his strategies for balancing impact and flexibility, the importance of continuous learning, and his passion for teaching and storytelling. Gib also talked about b...
Nov 18, 2024•49 min
Today’s episode is a re-release of one of our most popular episodes on the podcast: our conversation with Josh Doody, a renowned salary negotiation coach and author of Fearless Salary Negotiation . With the job market shifting and more people navigating complex career moves, we thought it was the perfect time to bring back Josh's invaluable advice on negotiating job offers. This episode covers why changing companies can be key to maximizing your compensation, the best practices for salary negoti...
Nov 07, 2024•48 min
Welcome to another episode of Supra Insider. This time, Marc and Ben are joined by John Cutler and Joshua Herzig-Marx (friends of the show) to explore a growing trend in the product community: product leaders struggling to find their next roles. We discussed the contributing factors to this trend, including the flattening of product organizations, the rise of super IC PMs, and the influence of AI. The conversation dives into practical advice for product leaders navigating these challenges and wh...
Oct 28, 2024•55 min
Welcome to another episode of Supra Insider. This time, Marc and Ben sit down with Ben Sprecher , CPO at an AI startup and a longtime product leader with 24 years of experience in AI. They explore Ben’s fascinating journey from founding a company that was acquired by Google to leading AI initiatives. In this episode, we dive into a futuristic bet Ben made 25 years ago on the future of AI, the concept of the "AI demo trap"—a pitfall many companies fall into—and actionable frameworks to avoid it. ...
Oct 23, 2024•41 min
