Zero to One: Product Journeys

Deepak Tiwari came up through engineering and strategy consulting at Accenture before moving into product, and his career has run through some of the most consequential AI and infrastructure builds of the last 15 years, across Google, Lyft, Turing, and Meta. At Turing, he served as CPO and built the training data platform used by OpenAI, Anthropic, DeepMind, and Meta. Before that, he helped take Google Cloud from fewer than $0 to $500M in annual revenue. He's now at Meta, leading product across ranking, relevance, and generative AI systems at Instagram scale.In this episode, we cover:What it took to pitch Google Cloud's CEO on a net-new product from scratch, and what happened when customers started using it in ways the team never anticipatedHow the enterprise transformation playbook that worked at Google Cloud became the blueprint for Turing's 10x growthWhat working directly with the frontier labs taught him about why data is the real moat in AIBuilding Meta's first generative AI ads product with no prior playbook, and reading transformer and diffusion model papers from scratch to understand what was actually possibleWhy the biggest drivers of user experience at Lyft had nothing to do with the app, and everything to do with backend MLThe three levers that actually improve a model, and why good PMs need to hold all three in viewWhy the manager who barely had time for one-on-ones taught Deepak the most important career lessonAn interesting conversation for PMs and product leaders who want to understand how AI products actually get built, from the infrastructure up.

Rajitha Chaparala has spent 20 years building data and AI products in some of the world's most heavily regulated industries. She founded Intralinks' AI Center of Excellence, scaled the data platform at ZoomInfo through two simultaneous acquisitions delivering eight figures of incremental revenue in year one, and has spent the last four years as VP of Product for Data and AI at Procore, bringing AI into one of the most document-heavy, safety-critical industries in the world.In this episode, we cover:How she built AI for M&A due diligence when she couldn't access actual customer documents, and why crowdsourcing training data on Upwork was the only path forwardThe redaction product that emerged as a happy accident from the same NLP foundation, and what that taught her about building on existing platformsThe five principles she used to run two massive parallel workstreams during ZoomInfo's acquisition integration, and why clarity of vision matters more than process when you're moving fastThe build vs buy decision at every company she's been at, and why the answer has been different every timeWhy human-in-the-loop isn't a limitation in construction AI, it's the right design for where accuracy and governance currently standWhy she hires for adaptability above everything else, and what breaks when you don'tA conversation for data and AI product leaders who want a grounded view of what it takes to build AI products in industries that don't forgive mistakes.

Firstly, welcome to Season 3, and thank you to all my listeners! Please follow and rate the show so I can keep bringing on incredible Product leaders on the podcast!Robert Hamilton has been building products since before the Web existed. He founded the world's first SMS search and shopping company in 1999, spent 8 years at Google shipping the Google Mobile App, Voice Search, and Nexus hardware, and helped build the Oculus VR platform before anyone had figured out headset retention. He now helps and coaches PMs and product leaders full-time to accelerate their careers. In this episode, we cover:What it was like building Scan Mobile in 1999, raising $10M, and learning that being early pays the same as being wrongHow Google approached app distribution before app stores existed, and what that bet taught the team about building for the futureThe real challenge of VR retention and why getting someone to put something on their head is harder than it soundsWhat keeps pulling Robert toward the frontier rather than the established thingWhy the biggest barrier holding PMs back has nothing to do with skills or AI toolsHis framework for PMs at every stage: increase clarity and drive progressA conversation for PMs who want to think differently about building, navigating platform shifts, and understanding themselves before they try to understand the technology. You can find out more about Robert's current work here.

How do you actually scale enterprise platforms inside companies like AWS, Google Cloud, and Stripe?In this episode of Zero to One, I sit down with Bob Krentler, former GM at AWS and Product leader at Stripe and Google Cloud, to break down what it really takes to build, operate, and monetize Enterprise-grade platforms at massive scale.Bob has led multi-billion dollar product lines, driven Enterprise modernization efforts across the cloud, and built vertical solutions powering some of the world’s most important companies.We cover:The biggest mistakes teams make when modernizing legacy infrastructureWhat AWS taught him about operating at true cloud scaleThe hardest trade-offs in enterprise, including competing with your own partnersWhy every horizontal platform eventually moves vertical, and how Stripe executed itWhat most product leaders get wrong about AI-first product strategyHow AI is reshaping the role of product, engineering, and decision-makingWhy enterprise requires long-term thinking, not short-term winsIf you’re building for Enterprise, thinking about Platforms, or trying to understand where AI fits into your roadmap, this episode is a masterclass in how the best operators actually think.

What did product look like before product management even existed?In this episode of Zero to One, I sit down with Joshua Burgin, former Chief Product Officer at Upwind Security and early Amazon employee, to break down how product thinking evolved from the earliest days of Amazon into today’s world of AI, cloud infrastructure, and platform-scale systems.Joshua has led product and engineering across AWS, VMware, and Zynga, building and scaling products from zero to billions in revenue.We cover:The origins of product management inside Amazon’s first 100 employeesThe biggest unsolved problems in cloud infrastructure and AWS todayHow pricing strategy impacts adoption in B2B SaaS and AI platformsWhat changes when AI makes products non-deterministicWhy observability, evals, and decision-making frameworks are now core PM skillsHow to balance speed vs stability when scaling product teamsThis episode is for product managers, product leaders, and builders working in AI, SaaS, and infrastructure who want to understand what’s actually changing, and what still holds true.Find more of Joshua’s work: https://www.joshuaburgin.io/

Sriram Iyer has spent the last two decades building and scaling enterprise platforms across Salesforce, Adobe, and Freshworks.Over that time, he has helped grow products from sub-$1B to multi-billion dollar ARR, working across platform strategy, AI systems, and now full general management with P&L ownership.In this conversation, we explore the journey behind those platforms and the decisions that shaped them.Sriram shares how he moved from consulting into product management during the early days of cloud computing at Salesforce, helped build intelligence layers that later evolved into Einstein AI, and later led the growth of Adobe’s Digital Video business from $700M to $2.2B ARR at Adobe.We also discuss his transition from product leadership into full GM ownership and what changes when you move from building products to building businesses.Topics we cover include:• Transitioning from consulting into product leadership• Building intelligence layers inside Salesforce before AI became mainstream• The technical and infrastructure challenges behind scaling Adobe’s video platform• What changes when product leaders take on GM and P&L ownership• Why AI is a generational technology wave and how enterprise adoption may evolve• Advice for product managers thinking about long-term careersA thoughtful conversation on platform thinking, enterprise AI, and the realities of scaling products inside large technology companies.

Product marketing sits at the intersection of product, sales, and growth, but it’s often misunderstood or treated as an afterthought.In this episode, I’m joined by Michael Rothschild, a product marketing leader who’s spent his career translating deeply technical products into stories that actually land with customers.We go deep on what product marketing really exists to solve, and where teams tend to get it wrong.We cover:How product marketing differs from traditional marketing, and why the distinction mattersWhat it really means to turn complex products into clear, customer-first narrativesLessons Michael carried over from teaching into product marketing leadershipHow product marketing should scale from early-stage companies to large enterprisesWhere launches, messaging shifts, and rebrands often break downHow to position highly technical products for C-suite buyers without losing substanceWhat product marketing should measure beyond pipeline and dashboardsThe role product marketing plays in making acquisitions actually workIf you’ve ever wondered how great products get misunderstood, or how teams can bridge the gap between what they build and how it’s perceived, this episode will be an interesting listen!

Welcome to 2026, and a new run of conversations on Zero to One.In this episode, I’m joined by Rama Veeraragoo, a founder and product leader who’s built across early-stage startups, scaled platforms, and now at the edge of agentic systems. Rama has led 0-1 product bets at Stripe and previously co-founded DocuVision.ai, an NLP and computer vision redaction company acquired by OneTrust, where he went on to lead the Data Redaction offering.We unpack what actually separates Founder PM mode from Traditional PM mode, not as a skills debate, but as a difference in operating systems. Survival versus scale. Rama shares hard trade-offs from building in deeply regulated environments, including what it takes to pause growth in one area to pursue a high-stakes bet in another.We also get into what building in fast-moving, poorly defined technical spaces demands from product leaders today, how to stay “hacky” inside large organizations, and why speed and deep product thinking have to coexist, especially as agentic systems reshape how software gets built.In this episode, we cover:Rama’s unconventional path into productWhy early-stage product often runs on intuition before dataFounder mode vs manager mode, and when each breaks downWhat feels genuinely different about building products in the agentic eraIf you’re building in ambiguity, or trying to balance speed with craft, you'll love this episode.

In this episode of Zero to One: Product Journeys, I sit down with Poornima Farrar, Chief Product Officer at Rival. Her career spans analytics, AI, and HR tech, with leadership roles at Alteryx through their IPO, at Workday shaping AI and HCM, and at Salesforce after the Tableau acquisition. Most recently, she led a full product and AI transformation at Rival.We explore her path from linguistics and academia into product, why she gravitates toward complex back office systems, and how she approaches the intersection of research, storytelling, and execution. Poornima shares how she evaluates trade offs, frames problems for AI driven products, designs product teams for hypergrowth, and builds alignment with exec and engineering partners.We also get into consolidation and product strategy, from deciding what to keep, cut or rebuild, to how modularity, connected experiences and analytics shaped Rival’s direction. She outlines the shift from systems of record to systems of intelligence and what the next decade of enterprise software could look like as AI orchestrates more of the work.A thoughtful deep dive for anyone building in HR tech, AI, or enterprise software.

On this episode of Zero to One, Sandy Huang joins me to unpack a career spent building and scaling category defining products across Minted, Flipboard, Amazon and GoodRx.We get into the early zero to one moments that shaped how she builds, from scrappy startup execution to leading multimodal search and shopping for Amazon. Sandy breaks down the core drivers behind the growth at Minted and Flipboard, why personalization moves the needle more than anything else, and how she thinks about flywheels in consumer and marketplace environments.We talk through what Amazon taught her about scale, writing, critical thinking and debate, and why those mechanisms still shape how she partners with founders and product leaders today.Sandy also shares a rare look into the process behind patenting technology, how she built her product sense through years of studying human behavior, and why sharpening judgment is becoming one of the most important skills for PMs in the AI era.We close with a deep dive on responsible AI, the shift toward senior IC tracks in product, and the advice she’d give the next generation of PMs as they build in a world of more tools, more noise and much higher expectations.A brilliant conversation with one of the most thoughtful product leaders in the field. Let’s get into it.

In this episode, Nathalie Criou joins Zero to One: Product Journeys to share insights from a career spanning Google, Amazon, Twilio, Docker, and her own start-up, RidePal.Nathalie talks about why every great product starts with a painful, expensive, human problem, what it means to stay married to the problem rather than the product, and how to balance innovation with customer readiness.We discuss lessons from scaling at Google Ads, navigating tough trade-offs at Amazon, and building product cultures grounded in humility, empathy, and clarity. Nathalie also shares her perspective on the future of product management, why focus beats force, and why, bad PMs will become extinct, and good ones will be dangerous.A thoughtful conversation on the craft of product, leadership at scale, and building systems that are both useful and joyful.

In this episode, I sat down with Ryan Johnson, CPO at CallRail, a $100M+ PLG company serving over 200,000 businesses. Ryan’s path into product wasn’t traditional - he started in finance and operations before scaling product orgs at companies like Virtue (acquired by Oracle), Banjo (SoftBank-backed), and now CallRail.We spoke about how he leads with transparency and trust, and what it takes to scale product in a high-growth, AI-driven company.In this episode:How CallRail launched its Voice AI assistant from POC to product in monthsNavigating trade-offs in AI onboarding, PLG vs sales motion, and time-to-valueWhat exec-level decision-making actually looks like from a CPO seatThe difference between fundraising stories and reality -from $100M rounds to Oracle acquisitionsHow to find your “PM stage fit” and build a career with self-awarenessIf you’re a PM navigating scale, new tech, or just figuring out what kind of product leader you want to become - this will be an fun and interesting listen!

Trust is one of the hardest things to measure in product, and one of the hardest things to earn.In this episode, Akshay Bhargava shares how he grew from early engineering roles into senior product leadership, with lessons from scaling security, developer tools, and observability products across Oracle, FireEye, Malwarebytes, 1Password, and New Relic.We cover:How stepping up as an engineering manager led him into productBuilding and launching Oracle’s first cloud security productThe product that helped Malwarebytes double revenue and save customers from ransomwareMoving 50+ products to consumption pricing at New RelicHow he operationalizes trust across different types of productsWhat he means by “coach and verify” and “purpose-built innovation”Why PMs who ignore AI today will be left behind tomorrowA thoughtful conversation with a leader who has shipped through complexity and scaled with conviction.

What does it take to go from warehouse operations to Senior PM at Amazon by 24, then build an AI platform that helps PMs level up faster?A special episode of Zero to One this week as we dive into entrepreneurship and product , I’m joined by Nabeel Khan, founder of Nayru and former Amazon product leader. At Amazon he owned product strategy for the software used to build the vast majority of their warehouses. Today he’s channeling those lessons into personalized, AI-driven upskilling for product talent.We cover:Breaking into product from ops and moving to Senior PM at 24Owning the toolchain that builds Amazon warehouses and consolidating 70 tools into a focused suiteThe tough trade offs in B2B at scale balancing current users with a future visionBuilding product sense through end to end process mapping, mentorship, and real user timeWhy he founded Nayru and how AI creates truly personalized learning plansOutcomes from the community including promotions to Director and VPPractical advice for PMs eyeing entrepreneurship runway, validation, and doing the role where you areHow AI will change the PM craft and why the role becomes more important, not lessNabeel shares a systems-first, practical playbook for growing as a PM, leading at scale, and turning learning into career acceleration. Hope you all enjoy!

What does it take to build products across every wave of innovation - from telecom and wearables, to crypto, AI, and enterprise SaaS?This week on Zero to One, I’m joined by Chander Chawla, a product leader whose journey has spanned startups and big tech alike. From co-founding Ever App to leading product at Open Garden and Meta, he’s consistently been at the edge of what’s next.In this episode we dive into:The lessons behind building products used by hundreds of millions, from public Wi-Fi to wearable techWhat it’s like betting $40M+ on a hardware product, and the foresight and fortitude it takesHow to simplify and earn trust when introducing complex tech like crypto and AI to everyday usersThe trade-offs he faced building in high-stakes environments, and the frameworks he leans on todayHis four-part framework for product leadership: user experience, profit, tech advancement, and competitive advantageWhy the best PMs lead with empathy, judgment, and communicationChander brings decades of perspective across industries, and this conversation is packed with insights for anyone looking to build with clarity, courage, and long-term impact.You can also follow his work at his blog and podcast!

How do you build products that can succeed in highly complex, regulated, and fast-changing enterprise environments?For the 11th episode, I’m joined by ⁠Palak Kadakia⁠, a product leader whose career has spanned Microsoft, UiPath, and now Trase. She’s led teams through IPO journeys, scaled enterprise platforms, and built AI-driven products designed to serve industries where precision and trust matter most.We dive into:• How to scale product orgs in hypergrowth while keeping customer trust at the center• What PMs often overlook when building for regulated industries• Balancing platform extensibility with simplicity in enterprise software• Lessons from navigating IPO readiness and product-market fit at UiPath• Building AI-driven products that solve real-world industry problems• How to approach strategy shifts - from corporate scale to startup urgency• The mindset shift needed when moving between enterprise giants and early-stage ventures• Her bold take on where enterprise product leadership is heading nextPalak shares candid lessons on building resilient teams, making high-stakes product calls, and creating impact across multiple stages of company growth.

What does it take to build a product org that can thrive across stages - from 0 to 1, and then to $100M+ scale?This week on Zero to One, I’m joined by ⁠⁠Ibrahim Bashir⁠⁠, a seasoned product executive whose career has spanned Kindle Fire, Twitter, Box, and Amplitude. He’s led high-impact product teams across B2B SaaS, platforms, and infrastructure, helping companies evolve from single-product to multi-product strategies.We cover:How to evaluate whether a product org is positioned for long-term successWhat product teams often overlook when expanding from one product to manyWhy product should be treated like a business, not a backlogBuilding product sense and recognizing what users actually needNavigating platform investments and customer trade-offsWhen extensibility strengthens your product - and when it doesn’tGrounding AI features in real user problemsThe mindset shifts needed when moving from IC to product leaderThe product decision that shaped his approachOne lasting insight for anyone building in today’s evolving landscapeIbrahim shares a thoughtful, systems-driven view of product, and what he’s learned from scaling teams, making hard calls, and building with intention.

What does it take to scale from a single-product company to a multi-product platform, without losing customer focus or speed?This week on Zero to One, I’m joined by ⁠Yair Levin⁠, a product leader who’s helped companies like SoFi, Gusto, Remitly and Velocity Global do just that. From launching new fintech products to leading platform teams and building with AI at scale, Yair brings a thoughtful, execution-first lens to complex product challenges.We cover:His 4-part validation framework to de-risk 0-1 betsLessons from scaling Gusto from payroll to multi-productHow SoFi prioritized stock vs. crypto using a clever painted door testBuilding AI as a problem-solver, not a shiny objectCreating moats through cross-product integrationThe biggest mindset shift for PMs trying to move into leadershipYair also shares the early product decisions that shaped his career, how he thinks about autonomy in product teams, and what to watch as AI continues to reshape the product landscape.

What does it take to build products that serve real, often overlooked customer needs, while aligning with both business goals and social impact?This week on Zero to One, I’m joined by ⁠Prashanthi Ravanavarapu⁠, a product leader whose career has spanned fintech, enterprise platforms, and mission-driven innovation. From her early days at PayPal to scaling teams at Workiva, she’s built inclusive, human-centered products that drive meaningful outcomes.We cover:How to approach product discovery for underserved usersWhat it takes to align customer value with profit and purposeStructuring resilient product strategy in fast-moving environmentsBuilding high-performing, mindset-driven product teamsThe product she’s most proud of — and the one she wishes she got to buildPrashanthi also shares her perspective on trade-offs, mentorship, and why PMs should treat their careers like a product.

In this episode of Zero to One, I’m joined by Krishnan Nair, SVP of Product at 21Co, whose journey spans from launching Samsung’s first Smart TV app marketplace to leading product in streaming and crypto. We unpack the lessons behind building regulated digital asset platforms, the frameworks he uses for product trade-offs, and how experimentation, data, and user-centric design have shaped his approach. Krishnan also shares predictions on stablecoins, tokenization, and advice for PMs making the leap to leadership.

On this episode of Zero to One, I sit down with Brian Huss, VP of Product at PrizePicks, where he’s helped scale the platform into one of North America’s fastest-growing sports apps. We talk about what it takes to build truly fan-first products, how to balance monetization with great UX, and the behind-the-scenes story of launching PrizePicks Arena. Brian also shares lessons on product leadership at scale, and where he sees the future of sports, gaming, and interactivity heading.

On this episode of Zero to One, I’m joined by Vivek Bedi, a product leader who’s built and scaled platforms at Goldman Sachs, LearnVest, Northwestern Mutual, and high-growth SaaS companies. We cover his shift from eng to product, how he approaches digital transformation in complex orgs, and why product leadership starts with empathy. He also shares takeaways from his book You: The Product, focused on how PMs can take control of their careers by treating themselves like a product. If you’re building in SaaS or Fintech, leading product at scale, or just thinking about your next career move, this one’s packed with insight.

On this episode, I’m joined by Nachi Periakaruppan, a Cybersecurity focused product leader with deep experience building security and mobile products at scale. He’s led teams at Oracle, McAfee, and Malwarebytes, shaping mobile security portfolios that protect millions globally.We talk about his tranistioning into product from engineering, the complexity of building user-first security on mobile, and why sometimes the best product decision is the simpler one.Nachi shares practical lessons on leading in regulated spaces, adapting to rapid market changes, and keeping your product strategy grounded in real customer need.

If you're curious on best practices when building for highly regulated industries across all scales, I’m joined by Errol Apostolopoulos, an B2B SaaS and AI focused product leader who’s built and scaled AI-powered SaaS platforms across Crimson Hexagon, Equifax, and Case IQ.We talk about his path from engineering to product, the lessons from scaling startups through IPO and M&A, and what it takes to build responsible, agentic AI systems in highly regulated environments.Errol shares his approach to leading with empathy, navigating unexpected trade-offs, and why understanding the commercial side of product is key to success. More about Errol on his website too.

How do you become a master of Product Led Growth in the age of AI? I’m joined by AJ Jindal, a product and growth leader who’s scaled PLG engines at Sentry and AppDynamics, founded and sold an AI-first SaaS startup, and now leads product at Rippling.We talk about how he transitioned from engineering to product, what it took to build and exit Fulcrum, and how he’s helped shaped the future of data activation at Census.AJ shares real-world lessons on building AI-first platforms, running high-impact PLG, and navigating the shift from founder to product leader.

For the 1st episode of Zero to One I’m joined by Andrew Ramm, a seasoned product and business leader who’s led major transformations at Amazon, Autodesk, and Avid. We talk about how he scaled AutoCAD globally, turned around Amazon’s Alexa Internet business, and what it really takes to lead product in high-complexity environments.Andrew shares practical lessons on org design, strategic clarity, and how product leaders can stay effective as their scope scales.