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 forward
• The redaction product that emerged as a happy accident from the same NLP foundation, and what that taught her about building on existing platforms
• The 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 fast
• The build vs buy decision at every company she's been at, and why the answer has been different every time
• Why human-in-the-loop isn't a limitation in construction AI, it's the right design for where accuracy and governance currently stand
• Why she hires for adaptability above everything else, and what breaks when you don't

A 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 wrong
• How Google approached app distribution before app stores existed, and what that bet taught the team about building for the future
• The real challenge of VR retention and why getting someone to put something on their head is harder than it sounds
• What keeps pulling Robert toward the frontier rather than the established thing
• Why the biggest barrier holding PMs back has nothing to do with skills or AI tools
• His framework for PMs at every stage: increase clarity and drive progress

A 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 infrastructure
• What AWS taught him about operating at true cloud scale
• The hardest trade-offs in enterprise, including competing with your own partners
• Why every horizontal platform eventually moves vertical, and how Stripe executed it
• What most product leaders get wrong about AI-first product strategy
• How AI is reshaping the role of product, engineering, and decision-making
• Why enterprise requires long-term thinking, not short-term wins

If 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 employees

• The biggest unsolved problems in cloud infrastructure and AWS today

• How pricing strategy impacts adoption in B2B SaaS and AI platforms

• What changes when AI makes products non-deterministic

• Why observability, evals, and decision-making frameworks are now core PM skills

• How to balance speed vs stability when scaling product teams

This 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 careers

A 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 matters

• What it really means to turn complex products into clear, customer-first narratives

• Lessons Michael carried over from teaching into product marketing leadership

• How product marketing should scale from early-stage companies to large enterprises

• Where launches, messaging shifts, and rebrands often break down

• How to position highly technical products for C-suite buyers without losing substance

• What product marketing should measure beyond pipeline and dashboards

• The role product marketing plays in making acquisitions actually work

  
  

If 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 product

• Why early-stage product often runs on intuition before data

• Founder mode vs manager mode, and when each breaks down

• What feels genuinely different about building products in the agentic era

If 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.