Supra Insider

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

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

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

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

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 users in days, not months.This episode is packed with insights on collaboration, prototyping workflows, and why the best AI builders might not be engineers.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

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 from working with founders on their first PM hire, while Mike reflects on his own job search and why structure, calibration and interviewer training are essential.If you're hiring your first PM or your 100th, this episode is full of practical advice to help you sharpen your process, catch bias early and avoid costly mis-hires.grows.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

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 than ever. Whether you're a founder, product leader, or operator, this conversation is packed with practical advice on how to step up as your company grows.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

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 humanity.They also dive into how job seekers can regain power in the process by getting crystal clear on what they want, leading with authenticity, and treating interviews like two-way conversations. Whether you're currently on the job market or hiring for your team, this episode is packed with insight on how to play the game better—from both sides.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

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, improving customer feedback loops, and empowering PMs to communicate ideas visually without waiting on design resources. Sanket also shares practical advice for introducing AI prototyping into your company - no matter the size, and how it can unlock faster cross-functional collaboration across product, engineering, and go-to-market teams.If you're a PM, designer, or founder looking for ways to make your product development cycles faster, sharper, and more collaborative, this episode is packed with actionable insights you can apply today.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

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 workflows, redefining prototyping, and collapsing traditional linear product development.We also get deep on the concept of taste—what it means to produce high-quality work in a world where the UI layer is increasingly commoditized. Plus, a live Bolt demo, the hidden risks of lazy thinking with AI, and why the future belongs to generalists with strong judgment and taste.If you're a PM, designer, or product leader trying to make sense of the new AI-powered stack, this one's 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

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—and why go-to-market remains the biggest bottleneck.They also explore why some companies still penalize failure, how team dynamics are evolving as PMs become more self-sufficient, and why embracing high-leverage work is more critical than ever. If you're a PM, solopreneur, or product leader trying to navigate the new AI era, this episode is packed with honest takes and practical advice.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

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 emerging in AI-native organizations, and how simulations, knowledge graphs, and organizational ontologies might shape the next generation of work. Whether you're a product leader, founder, or operator curious about the frontier of product ops and AI tooling, this episode offers tons of insight—and inspiration.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

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 supporting humans and AI working together in real time—and what that means for interface design, trust, and product differentiation.Steven also shares how he's staying ahead of the curve by studying patterns across tools like Figma, Notion, Stripe, and Claude—and how building great developer tools today means thinking about developer experience and end-user UX at the same time.Whether you're a founder, product leader, or designer thinking about how AI might shape your product, this episode offers a grounded and inspiring look at what's coming next.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

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 growth. Phil also shares how he uses AI tools to save hours each week—from custom GPTs to automated sales prep—and why relevance beats personalization in modern outbound.If you're a product leader curious about starting your own business, or a founder looking to improve your GTM strategy and use AI more effectively, this episode is packed with practical insights.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

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 development process, the importance of hands-on tinkering, and why AI needs to earn trust before it can take over critical workflows.Whether you're a PM, designer, or engineer working on AI features—or just curious about how a large tech company approaches AI—this episode is packed with insights.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

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 psychological safety in their teams. Randhir also shares practical frameworks for improving team collaboration, handling difficult conversations, and fostering a culture of trust.If you're a product leader looking to sharpen your leadership skills, a founder building a team, or someone navigating tricky workplace dynamics, this conversation is packed with actionable takeaways.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

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 about automation in their work. We explore the real-world challenges of implementing AI, why human-in-the-loop remains crucial, and how AI is transforming tasks like content creation, customer insights, and product management.We also discuss the role of AI in product strategy, how to evaluate what's possible today vs. what will be possible in the near future, and why PMs who don't actively experiment with AI risk falling behind. If you're trying to make sense of AI's impact on product work, 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

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 interested in AI's impact on product development, don't miss this episode!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

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 through a live demo, showing how to prototype and test a new hypothetical AI LinkedIn feature in real time. If you're a PM looking to move faster and validate ideas more efficiently, 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

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're a product leader considering new career paths or someone seeking actionable tips for personal growth, this conversation is packed with insights.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

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

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

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

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

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

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

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

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

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

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 building engaging content, like his well-loved product strategy workshops, and organizing the Product Leader Summit. Whether you're a product leader looking for practical insights or someone seeking inspiration to live a more fulfilling life, 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

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 negotiation, and common mistakes to avoid. It's packed with practical strategies and tips to help you approach salary discussions with confidence and make the most of your opportunities. This is a must-listen for anyone preparing for interviews or hoping to elevate their career trajectory.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

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 what the future might hold for product leadership.For anyone who is navigating the evolving product management landscape, considering a career transition, or interested in how AI and organizational shifts are reshaping the role of product leaders, this episode is 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

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.If you're a founder, product manager, or someone looking to enhance your AI strategy, this episode is packed with valuable insights and actionable advice to help you navigate the evolving landscape of Artificial Intelligence.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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Alex Hanthorn (Drift, TripleByte, Nielsen) to explore the evolving world of user research. From scrappy research methods in early-stage startups to the more formalized processes at large tech companies, we delve into the challenges and opportunities of understanding user motivations. Alex shares insights from his experiences, including his time working with companies from Taco Bell, and discusses the art of balancing intuition with data. This episode is packed with actionable advice for founders, product managers, and anyone looking to improve their approach to user research.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

Welcome to another episode of Supra Insider. This time, Marc and Ben are joined by Varun Puri, CEO and co-founder of Yoodli, a platform helping people improve their public speaking skills. Varun shares his journey from working with Sergey Brin at Google to taking the leap into entrepreneurship. The conversation delves into Varun's time at Google X, the early days of building Yoodli, the harsh realities of founding a company, and the joys of actually making a difference. This episode is a must-listen for aspiring founders and product leaders who want to hear an honest account of the highs and lows of startup life.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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Melissa Chi, COO and former head of product at Pathpoint. We explore Melissa's transition from a product leader to COO, the importance of maintaining user empathy in a remote, operations-heavy environment, and how she continues to support and coach her team. Melissa also shares insights on managing time effectively, fostering cross-functional collaboration, and prioritization in a growth-stage startup. This episode is a must-listen for anyone looking to grow their career in leadership while maintaining a user-centered approach.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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with longtime friends and co-founders, Joshua Herzig-Marx and Ben Sprecher, to explore their journey from childhood friendship to building a company that was acquired by Google. In this candid conversation, Joshua and Ben share their co-founder origin story, the challenges they faced scaling a startup, and how they managed their relationship through the ups and downs of entrepreneurship. They also dive into the crucial lessons learned from hiring a CEO, pivoting their business model, and making tough decisions to ensure a successful exit. This episode is packed with invaluable insights for anyone thinking about finding a co-founder or navigating the early stages of a startup.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

Welcome to another episode of the Supra Insider. This time, Ben and Marc are joined by Katie Kent, who shares her unique experience transitioning from a product leadership role back to an individual contributor (IC) as a staff PM at Semgrep. Katie talks about how her background in leadership has sharpened her skills as an IC, the lessons she's learned from the security industry, and why she believes in staying hands-on with product work. The conversation explores the value of remote and hybrid work, the evolving role of tools like FigJam in fostering collaboration, and what it means to bring joy and delight into B2B products. Whether you're a PM considering a career shift or looking to deepen your strategic thinking, this episode offers a wealth of 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

Welcome to another episode of Supra Insider. This time, Mark and Ben sat down with Josh Brewer, former CEO and Co-founder of Abstract, to discuss the nuances of creative leadership in today's fast-evolving tech landscape. Josh shares his unique perspective on building high-performing teams, delegating effectively, and fostering an environment of openness and authenticity. The conversation delves into the concept of "founder mode," the future of design amidst AI advancements, and the critical role design plays in shaping product vision and business strategy. Tune in for actionable insights and lessons from Josh's extensive experience in product management, design, and entrepreneurship.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

Welcome to another episode of Supra Insider. This time, Mark and Ben explore the timely topic of taking time off. Recently returning from their own breaks, they share experiences, insights, and reflections on the value of truly unplugging. The conversation delves into their activities during time off, common challenges of stepping away from work, and effective strategies for fully disconnecting. They also discuss the personal benefits experienced and the lessons learned, which they are excited to apply moving forward.For anyone considering a break or just returning from one, this discussion is meant to inspire and offer practical advice on making the most of downtime.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

Welcome to another episode of Supra Insider. This time, we feature Brenton Sellati, a seasoned product leader who went from managing four teams to leading 50 at Wayfair. Brenton introduces his framework for exponential growth, focusing on critical thinking, problem-solving, and influencing skills. He shares how applying these principles to his career led to rapid advancement and offers practical advice for PMs at all levels. This episode is packed with insights for anyone looking to elevate their product management game. We highly recommend you watch this episode on YouTube since Brenton used slides throughout the episode.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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Rich Mironov, an experienced product leader and 6x interim CPO, about the challenges of managing product strategy in sales-driven environments. We discussed building better relationships between product and go-to-market teams, why burnout is so common among product leaders, and how to thrive in these high-pressure roles. This conversation is a must for anyone navigating the complex dynamics of product leadership, especially in a B2B environment.All episodes of the podcast are also available on Spotify, Apple and YouTube (video).In this episode, we covered the following topics:* The challenges product leaders face in balancing the needs of go-to-market teams with long-term product strategy* The importance of understanding incentives and timelines in sales-driven organizations* Why empathy and relationship-building with cross-functional teams are crucial for successful product management* Common misconceptions about the roles and motivations of sales and marketing teams* Strategies for product leaders to influence executive decisions and prioritize effectively* The increasing trend of burnout among product leaders and practical advice for managing stress and expectations* Rich's thoughts on how to assess company culture and leadership dynamics during a job search to ensure a good fit* And more!If you'd like to watch the video of our conversation, you can catch that on YouTube: Links:* Rich Mironov's Product Bytes: https://www.mironov.com/* Rich's article on CPO burnout: https://www.mironov.com/cpo-burnout/* Rich's article on why prioritization is about politics: https://www.mironov.com/pri-politics/* Rich: https://www.linkedin.com/in/richmironov/* 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

Welcome to another episode of Supra Insider. This time, Marc and Ben sat down with Allison Braley, partner and head of marketing at Bain Capital Ventures. This episode delves into common marketing and communications mistakes made by founders, the importance of an authentic online presence, and how to build effective partnerships between product leaders and marketers. We also touched on Allison's transition from an operational marketing leader role to supporting founders as a VC and why this new role plays to her strengths. This episode is essential for founders looking to enhance their marketing strategies and get more leverage out of their marketing leaders.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

Welcome to another episode of Supra Insider. In this episode, Marc and Ben sit down with Chris Hulls, the founder and CEO of Life360, the world's leading location-sharing app for families. This episode is a must-listen for anyone interested in scaling a tech startup and Welcome to another episode of Supra Insider. In this episode, Marc and Ben sit down with Chris Hulls, the founder and CEO of Life360, the world's leading location-sharing app for families. This episode is a must-listen for anyone interested in scaling a tech startup and understanding the intricacies of product management in a rapidly growing company. the intricacies of product management in a rapidly growing company.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

Welcome to another episode of Supra Insider. This time, Marc & Ben sat down to talk about Ben's recent experience launching a course on Maven. This episode will be extremely relevant to anyone considering launching a course.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

Welcome to another episode of Supra Insider. This time, Ben joined Estee Goldschmidt on her podcast, The Estee Show, to dive into Ben's learnings from the past six months of fractional product work.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

Welcome to another episode of Supra Insider. This time, we're excited to bring you our second conversation with Josh Herzig-Marx (a follow up on episode 16). Josh was one of the early facilitators in Supra, has been a successful founder who sold his company to Google, held multiple early stage product leadership roles, and in recent years has found meaning in his role as an early stage product coach.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

Welcome to another episode of Supra Insider. This time, we're excited to bring you our conversation with Heather Phillips, Senior Director of Product Design at Slack.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, we're excited to bring you our conversation with Josh Herzig-Marx. Josh was one of the early facilitators in Supra, has been a successful founder who sold his company to Google, held multiple early stage product leadership roles, and in recent years has found meaning in his role as an early stage product coach.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. After Ben shared a fun story on LinkedIn about how he got his first tech job, we thought it would be fun to do an episode about how we landed our first jobs in tech.New to the pod? Subscribe below to get the next episode in your inbox

Welcome to another episode of Supra Insider. This time, we're excited to bring you our conversation with Kelly O'Shaughnessy, Head of Product - Self Serve at Airtable.New to the pod? Subscribe below to get the next episode in your inbox