The Product Podcast

Product School

Hosted by Product School CEO Carlos Gonzalez de Villaumbrosia, The Product Podcast drills deep into the minds of Chief Product Officers from Cisco, Lovable, Perplexity, Shopify and many more.  We move beyond high-level theory to reveal how top executives actually lead in the age of AI. We dig deep into their real-world decision-making, strategic frameworks, and the operational playbooks used to build intelligent products. If you are a VP, Director, or CPO looking to drive innovation at scale, this is your essential listen.

  1. 2d ago

    Toast VP of Product on Building Agents Into Pre-AI SaaS; Shipping AI Into a 14-Year-Old Platform and Building for the Real Economy

    Toast was built long before generative AI existed. So how do you weave AI agents into a platform that thousands of restaurants already run their business on, without breaking the thing that works? In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Maggie Crowley, VP of Product at Toast, to unpack what it actually takes to build AI into mature, pre-AI SaaS. Maggie is a former Olympic speed skater (fifth at the 2006 Winter Olympics) turned product leader, with an MBA from Harvard and product roles across Drift, TripAdvisor, and Charlie Health before Toast. She was also a Product School contributor years ago, back in her Drift days, which is what makes this a fitting return. At Toast she leads product on Toast IQ, the company's AI layer for restaurant and retail operators. In this conversation, she and Carlos get into the genuinely hard parts: why the quality bar for building on an established platform is punishingly high, how her team actually shipped their first assistant (sitting in WhatsApp groups with real customers and turning it on for a few of them), and why you have to physically bring the AI to the user instead of assuming they'll discover it. Maggie is refreshingly blunt that restaurant operators have zero tolerance for "AI for AI's sake." They don't care whether it's Anthropic, OpenAI, or an open-weight model under the hood; they only care whether you helped them run their business. She explains how the tight P&L of a restaurant forces real discipline about what's worth charging for, how Toast IQ Grow (an agent that drives demand and fills seats) became a breakthrough use case by slashing the cost of marketing work, and why she still manages a frontline team directly to stay close to how AI is changing the way products get built. The episode closes with a live demo of Toast IQ. What you'll learn: - How to build AI agents into a platform designed years before AI, without lowering the quality bar - The scrappy build process: WhatsApp groups with customers and turning an assistant on for a few - Why you have to bring the AI to the user, and why AI onboarding is an unsolved problem - Why context (where the user is, what time, what role) is everything for an AI product - Why restaurant operators have zero tolerance for "AI for AI's sake" - How the tight P&L of a restaurant enforces discipline about what's worth building and charging for - How Toast IQ Grow uses AI to cut the cost of marketing and drive real demand - Why abstracting model choice (Anthropic vs. OpenAI vs. open weights) away from the user matters - Why a product leader should keep a hand in how teams build, and manage close to the work - A live look at Toast IQ answering real operator questions in plain language Connect with Maggie Crowley: VP of Product, Toast LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/ Host: Carlos, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Toast: Toast is an all-in-one platform built for restaurants and retail, spanning point of sale, payments, operations, and marketing, now including Toast IQ, its AI layer for operators. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    Toast VP of Product on Building Agents Into Pre-AI SaaS; Shipping AI Into a 14-Year-Old Platform and Building for the Real Economy
  2. Sep 16

    Hinge CPTO on Building an App Designed to Be Deleted, Merging the CPO and CTO Roles, Chasing $1B in Revenue Without Chasing Engagement | Ben Celebicic | E312

    Most apps optimize for time on screen. Hinge optimizes for you leaving. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Ben Celebicic, Chief Product and Technology Officer at Hinge, the dating app "designed to be deleted," to unpack how you build a product whose North Star is great dates, not engagement, and still chase a billion dollars in revenue. Ben has been at Hinge for 11 years, since the 2015 relaunch, and recently became one of a growing number of leaders to hold both the product and technology mandate in a single CPTO role. He and Carlos get into the healthy tension between the CPO instinct (ship fast, innovate) and the CTO instinct (protect quality and infrastructure), and how he now runs that debate inside one person and across a team of nearly 300. He lays out Hinge's monetization philosophy in two principles: build the free experience so everyone can succeed, and only charge for things you can't give away free without breaking the ecosystem (which is why fewer than 15% of users pay). He explains how a dedicated culture and consumer insights team studies real daters to find core needs, how generative AI now enables per-user profile coaching that was impossible before, why trust and safety makes up roughly a third of the entire Hinge organization, and where he draws the line on AI-assisted engineering today. He closes on Hinge's mission to reach $1 billion in revenue in 2027. What you'll learn: - Why "designed to be deleted" is a real product principle, and how an anti-engagement North Star works - How to run the CPO-vs-CTO tension, even when both roles live in one person - Hinge's two-principle monetization model, and why fewer than 15% of users pay by design - Why you should only charge for things that would break the ecosystem if they were free - How a culture and consumer insights team turns real dater problems into features - How generative AI enables personalized profile coaching that wasn't possible before - Why trust and safety is about a third of the whole org, and how AI powers it - Where an engineering-background leader draws the line on AI-built product today - The mission to hit $1B in revenue in 2027, and the "obsess over user needs" formula behind it Connect with Ben Celebicic: CPTO, Hinge LinkedIn: https://www.linkedin.com/company/lrb-podcasts/about/ Host: Carlos, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Hinge: Hinge is the dating app "designed to be deleted," built to help people get off the app and out on great dates. Founded by Justin McLeod and relaunched in 2015, Hinge is part of Match Group's portfolio of dating and social discovery apps. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    Hinge CPTO on Building an App Designed to Be Deleted, Merging the CPO and CTO Roles, Chasing $1B in Revenue Without Chasing Engagement | Ben Celebicic | E312
  3. Sep 9

    Bolt CEO on Turning AI Prototypes Into Production Code Engineers Trust, the Story Behind a 5M-to-20M ARR Ramp in Two Months | Eric Simons | E311

    One month before Bolt exploded, Eric Simons was preparing to wind the company down. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Eric Simons, CEO of Bolt, to tell the story behind one of the fastest revenue ramps software has ever seen, and what he learned building toward it for seven years first. Eric is a high-school dropout who approaches life from first principles and treats endurance sports as training for the pain of building a company. He and Carlos trace the near-death moment (a board meeting set to start spinning the company down was one month away), the bet on WebContainers (an operating system Eric's team wrote to run in WebAssembly inside the browser, so you can build real full-stack apps from a browser tab, the way Figma brought design to the web), and the ramp that followed: zero to about $5M ARR in the first 30 days, then to roughly $20M ARR within two months, a curve that normally takes companies years. He explains why StackBlitz is now going deep on professional builders (PMs, designers, engineers), how Bolt is solving the hard part of turning AI-generated prototypes into production code your engineering team will actually sign off on, and why he frames the market like the ChatGPT-vs-Anthropic split: pick a specific ICP and workflow instead of spraying money at everything. He closes on the open-weights bet (StackBlitz was the earliest backer of Vite), aggressive usage-based pricing, and why cheaper open models are closing the last bit of distance to the labs. What you'll learn: - The near-death story: one month from shutting down, then a record revenue ramp - Why the WebContainer bet (a real OS running in the browser) took seven years and made Bolt possible - What a 0-to-$20M-ARR-in-two-months curve actually looks like, and why it's so rare - Why StackBlitz is focusing on professional product builders, not just cute prototypes - How to turn an AI prototype into production code your engineering team signs off on - The "ChatGPT vs. Anthropic" framing: why going deep on one ICP beats spraying money everywhere - Why first-principles thinking and endurance sport shape how Eric builds - The open-weights bet, aggressive usage-based pricing, and open models catching up to the labs Connect with Eric Simons, CEO, Bolt LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/ Host: Carlos, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Bolt / StackBlitz: StackBlitz is the company behind Bolt (bolt.new), an AI-powered web development platform that lets anyone build real full-stack applications from a browser tab, powered by its in-browser WebContainer operating system. StackBlitz was also the earliest backer of the open-source Vite project. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    Bolt CEO on Turning AI Prototypes Into Production Code Engineers Trust, the Story Behind a 5M-to-20M ARR Ramp in Two Months | Eric Simons | E311
  4. Sep 2

    Anthropic Member of Technical Staff on Leading Forward-Deployed Engineers, Turning Down 2x Pay, and Why Leaders Are Becoming ICs Again | Amandeep Khurana | E310

    What do you do after you've founded a company, sold it to Databricks, and could coast? Amandeep Khurana went back to being hands-on. In this episode of The Product Podcast, Carlos Gonzalez de Villaumbrosia (CEO at Product School) talks with Amandeep Khurana, now on Anthropic's go-to-market team, about a career built on deliberately choosing the harder path. Amandeep traces the whole arc: training as an engineer, moving to the Valley to go customer-facing at Cloudera, catching the company-building bug "by osmosis," and founding Okera in 2016, which eventually exited to Databricks. He talks about what he learned in the ups and downs of running a startup, why he later joined AWS as a founding PM (on Kiro) to run four zero-to-one initiatives instead of taking a comfortable management track, and how he thinks about the two fundamental jobs in any company: building a product and selling a product. He and Carlos dig into the tension between being a hands-on builder and being a manager, how to decide which domains are worth jumping into when you know nothing, and why he joined Anthropic to work on bringing AI safely to enterprises. It's a candid conversation about career design, first-principles decision-making, and staying close to the work. What you'll learn: - Why Amandeep repeatedly chooses the "harder path," and how first-principles thinking drives his career decisions - What founding and exiting Okera (to Databricks) actually taught him about company building - Why he went back to hands-on building instead of a pure management track - How to think about the two core jobs in any company: building the product and selling it - How to decide whether to jump into a domain you know nothing about - What running four zero-to-one initiatives inside a big company teaches you - Why he moved into GTM and enterprise AI adoption at Anthropic - How to stay hands-on as your career pulls you toward management Connect with Amandeep Khurana: Anthropic (GTM / Enterprise); previously co-founder and CEO of Okera, founding PM for Kiro at AWS LinkedIn: https://www.linkedin.com/in/amansk/ Host: Carlos Gonzalez de Villaumbrosia, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    Anthropic Member of Technical Staff on Leading Forward-Deployed Engineers, Turning Down 2x Pay, and Why Leaders Are Becoming ICs Again | Amandeep Khurana | E310
  5. Aug 26

    Mural CPO on How to Put AI in Multi-Player Mode for Your Team; Why AI Made Work Lonelier, Not Better | Elaina O'Mahoney

    Visual collaboration is missing from the AI era. That's the provocation Elaina O'Mahoney, Chief Product Officer at Mural, brings to this episode of The Product Podcast with Carlos (CEO at Product School). We spend all day alone in our tools, typing or talking to an LLM, and when it's time to collaborate we drop words into a doc instead of thinking together visually. Elaina makes the case that AI has quietly turned work into "solo-player mode," and that the teams who win next will be the ones who rebuild shared context and multiplayer collaboration on top of it. Elaina and Carlos get into why ideas are now cheap (you can go from a thought to a working prototype in hours) and why that makes shared context, not idea generation, the real bottleneck. She argues that everyone is a designer at heart, that product leaders should replace the five-page strategy doc with a fast prototype that conveys the North Star, and that "shipping" can mean a workflow or an agent, not just a production release. They also dig into the crowded "where work happens" landscape (Slack, Teams, Jira, Linear, Notion) and the blank-canvas gap around how and why decisions actually get made, how to create safe spaces for people to try AI and fail inside large enterprises, and the pricing tension between legacy seat-based SaaS and AI-native usage models. What you'll learn: - Why Elaina says visual collaboration is "absent" in the AI era, and why that matters - The "solo-player mode" problem: how AI made work lonely, and what multiplayer should look like - Why ideas are now cheap, and how that shifts the bottleneck to shared context and faster decisions - Why the real blank space isn't planning or chat, but how and why decisions get made - The case that everyone is a designer, and how visual thinking speeds up decisions - How a CPO ships to demo a direction (a prototype instead of a strategy doc) - What's still scarce in an AI world: data science, taste, and synthesizing analytics - How to create safe, low-risk spaces for teams to try AI and fail inside big enterprises - Why smaller "champion" teams beat top-down rollouts, and how internal builders spread practices - The pricing dilemma: seat-based SaaS vs. AI-native usage models Chapters: 00:00 Intro 00:59 Intro: Elaina O'Mahoney, CPO at Mural 01:31 Mural's origin as a collaboration canvas 03:01 Multiplayer vs. AI's solo-player mode 04:23 Ideas are cheap now: idea to prototype in hours 05:44 The competitive landscape and convergence 08:31 The blank space nobody owns: how decisions get made 09:22 Lowering the bar so everyone can design 11:33 Everybody should be shipping now 12:25 Shipping to demo, not to production 14:04 Creating safe spaces to try AI in the enterprise 17:10 Forward-deployed engineers 19:14 Building a community around Mural 22:11 The pricing dilemma: SaaS vs. AI-native usage 24:07 Measuring real AI impact 26:19 How Elaina structures her team 28:20 The innovator's dilemma 30:03 From annual QBRs to monthly loops 31:05 Ten years of Mural, and a World Cup sign-off Connect with the Guest: Elaina O'Mahoney, Chief Product Officer, Mural LinkedIn: https://www.linkedin.com/in/eomahoney/ Host: Carlos, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Mural: Mural is a visual collaboration platform built for teams to brainstorm, converge, and make decisions together on a shared canvas. Originally created by co-founders in Argentina, it scaled rapidly during the shift to remote work. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    Mural CPO on How to Put AI in Multi-Player Mode for Your Team; Why AI Made Work Lonelier, Not Better | Elaina O'Mahoney
  6. Aug 19

    Square Global Head of Product on: How to Build AI Agents People Actually Use, Why $49B Company Got Rid of General Managers | Willem Avé

    Two years ago, Square tore up its general-manager model and rebuilt the entire company around functional excellence. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Willem Avé, Global Head of Product at Square (part of Block), to unpack why they made that bet, what it costs, and how AI is now reshaping the org itself. Willem started at Block as a CTO whose company was acquired, grew up through engineering, and has seen every era of the company from the little white card reader to today's multiple product ecosystems. He explains why orgs should be built around customer outcomes (and how quality degrades the further you drift from that principle), why hardware demands a different kind of craft than software, and how Jack Dorsey's thinking pushed them toward the idea of running Block like a "mini AGI company," where AI encodes institutional knowledge instead of red tape and process. Then he opens up a live demo of "manager bot," an agent that lets a small-business owner delegate real tasks (like an inventory workflow for a bakery) without worrying about memory, connectors, or prompts. He closes with a genuine hot take on TAM and what AI agents mean for the size of the market Square can serve. What you'll learn: - Why Square replaced general managers with a fully functionalized org, and what "functional excellence" buys you - How to organize teams around customer outcomes, and why quality drops the further you drift - Why hardware craft (approachable, reliable, "it just works") differs from software craft - What it means to run a company like a "mini AGI," and how AI can encode knowledge instead of process - Why the era of the simple question-answer chatbot is ending, and what replaces it - A live look at "manager bot": delegating real business tasks to an agent - Why small-business owners want outcomes, not memory, connectors, or prompt-craft - Willem's hot take on TAM, and how agents expand who Square can serve - Why economic empowerment and democratizing advanced technology is the throughline Chapters: 00:00 Trailer 01:32 Inside Square and Block: how the teams are designed 03:34 The four orgs: audiences, platform, growth, money 04:46 Marrying hardware and software in one function 05:56 Finding leaders who understand both worlds 07:25 The DRI model and killing the silent veto 09:16 Can everyone report to one person? 11:12 Why flat orgs still need great managers 12:41 Building for people who are not on X every day 14:41 The loneliness of running a business 17:24 Demo: Manager Bot doing real work 20:19 Why AI should not create more work for sellers 22:13 Hot take: TAM is almost infinite 24:22 Killing the fragmented point solution stack 26:06 WhatsApp, Instagram, and the comms problem 27:54 Buzz and what nobody has solved yet 28:34 Closing Connect with Willem Avé: Global Head of Product, Square (Block) LinkedIn: https://www.linkedin.com/in/willem-ave/ Host: Carlos, CEO at Product School: LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Square: Square, part of Block, builds payments hardware and software plus a broader ecosystem of tools that help sellers and small businesses run and grow. Block also includes Cash App and other brands. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    Square Global Head of Product on: How to Build AI Agents People Actually Use, Why $49B Company Got Rid of General Managers | Willem Avé
  7. Aug 12

    How Skydio Ships Flying Robots With Just 20 Product Managers

    Most people think of drones as toys. Alden Jones thinks of them as infrastructure. In this episode of The Product Podcast, Carlos (CEO at Product School) visits Skydio's California office to sit down with Alden Jones, VP of Product at Skydio, the autonomous drone company building "flying robots" for public safety, defense, and infrastructure inspection. With a history degree and a military background (he was a truck-driving officer running supply convoys in Iraq) rather than an engineering one, Alden explains how a vertically integrated company of nearly 1,000 people builds everything in house, from chip-level design to hardware, embedded software, and cloud, and why autonomy, not just flight, is the real product. He breaks down Skydio's "Drone as First Responder" (DFR) program, where a drone often reaches the scene before human officers, and the outcomes dashboard cities use to track response times. He compares the economics against police helicopters (roughly $3,000 an hour to operate and $10-25M to buy), walks through the defense and tactical ISR use cases shaped by the war in Ukraine, and explains how thousands of cheaper camera drones could democratize air support while saving lives. He covers physical security (where 90-95% of alarms turn out to be false), the work of earning FAA trust to unlock groundbreaking waivers, and why Skydio's $3.5B, five-year investment in US and allied supply chains is funded by revenue instead of debt. He also opens up the product org itself: roughly 20 product managers across the entire stack, "strike teams" that work like forward-deployed engineers, and a customer-first culture where PMs are expected to go watch the robot fly in the real world. What you'll learn: Why Skydio calls its products "flying robots," and the "toys to tools to infrastructure" thesisWhat full vertical integration looks like: chip-down design to cloud, all in houseHow "Drone as First Responder" changes 911 response, tracked in a live outcomes dashboardThe real economics of drones vs. police helicoptersHow the war in Ukraine reshaped Skydio's thinking on tactical ISR and democratizing air supportWhy 90-95% of physical security alarms are false, and how autonomous drones clear them at near-zero marginal costHow Skydio earns FAA trust to fly beyond visual line of sight and win first-mover waiversWhy a $3.5B, five-year US manufacturing commitment is funded by revenue, not debtHow one pilot flying multiple drones becomes possible only through real autonomyHow Skydio runs product with ~20 PMs, "strike teams," and a customer-first org designWhy shipping hardware plus software (the Tesla comparison) shapes a roughly two-year program cycleConnect with Alden Jones, VP of Product, Skydio: LinkedIn: https://www.linkedin.com/in/aldenljones/ Host: Carlos, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Skydio: Skydio is a US-based manufacturer of autonomous drones ("flying robots") for public safety, defense, security, and infrastructure inspection. Founded in 2014 and headquartered in California, the company is vertically integrated across hardware, autonomy software, and cloud. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    How Skydio Ships Flying Robots With Just 20 Product Managers
  8. Jul 29

    How to Know Your AI Feature Actually Works (n8n's Founder's Metric) | Jan Oberhauser, CEO n8n

    n8n's founder puts the company's GitHub repo, nearly 200,000 stars, right next to the paid signup button, and he's genuinely fine if you never pay. In this episode of The Product Podcast, Carlos (CEO at Product School) sits down with Jan Oberhauser, CEO of n8n, the open-source automation platform that's crossed $100 million in ARR at a $5.2 billion valuation. Jan breaks down the "fair-code" license bet that let him give the product away and still build a business, how that free version became the on-ramp into enterprises like Meta, Nvidia, Dell, Accenture, Vodafone, Deutsche Telekom, and Mercedes, and why he believes the people with the problem should build the automation themselves, not a centralized team or an outside agency. He also walks through a live build of a personal AI agent (email and calendar), shows how n8n falls back from Claude to GPT via OpenRouter when a model isn't available, and explains how enterprises get automations into production faster because each agent can only do exactly what it's been permitted to do. What you'll learn: Why n8n rejected traditional open source for a "fair-code" license, and how it avoided the community backlash that burned other companiesWhy trust and consistency, not features, are the real center of a communityHow the free, self-hosted version drives bottom-up adoption inside major enterprisesWhy "sprinkling AI on top" kills products, and what to build insteadHow to chain agents so one agent's output becomes the next agent's inputWhy n8n is the "connective tissue" between models, tools, and business systemsHow guardrails (an agent can only do what it's explicitly allowed) speed up enterprise procurement and productionWhy the people with the problem should own the building, not a centralized AI teamHow 10,000+ community templates and 500+ integrations expand what non-technical builders can shipHow one company routes 75% of support through an n8n agent, with customers happier than with humansConnect with Guest (Jan Oberhauser): LinkedIn: https://www.linkedin.com/in/janoberhauser X: https://x.com/JanOberhauser Host: Carlos, CEO at Product School LinkedIn: https://www.linkedin.com/in/villaumbrosia/ About Jan Oberholzer: Jan is the CEO of n8n, an open-source (fair-code) workflow automation and orchestration platform for building AI agents. He started the company over seven years ago, before LLMs went mainstream, and has grown it past $100M ARR at a $5.2B valuation. About the Product Podcast: Product School's podcast brings you candid conversations with the founders and product leaders shaping tech. Social Links: Find out more about Product School hereFollow our Podcast on TikTok hereFollow Product School on LinkedIn here

    How to Know Your AI Feature Actually Works (n8n's Founder's Metric) | Jan Oberhauser, CEO n8n
4.3
out of 5
169 Ratings

About

Hosted by Product School CEO Carlos Gonzalez de Villaumbrosia, The Product Podcast drills deep into the minds of Chief Product Officers from Cisco, Lovable, Perplexity, Shopify and many more.  We move beyond high-level theory to reveal how top executives actually lead in the age of AI. We dig deep into their real-world decision-making, strategic frameworks, and the operational playbooks used to build intelligent products. If you are a VP, Director, or CPO looking to drive innovation at scale, this is your essential listen.

You Might Also Like