Inside AWS, Stripe & Google Cloud: The Hard Truth About Scaling Enterprise Platforms | Bob Krentler

Build vs Buy, Acquisition Integration, and Launching Agentic AI in Construction | Rajitha Chaparala

Rajitha Chaparala [https://www.linkedin.com/in/rajithachaparala/] 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.

Building Across Every Platform Shift - Google, Oculus VR and Beyond | Robert Hamilton

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 [https://www.linkedin.com/in/roberthamiltoncoach/] 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 [https://www.accelerationcoach.com/].

Inside AWS, Stripe & Google Cloud: The Hard Truth About Scaling Enterprise Platforms | Bob Krentler

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 [https://www.linkedin.com/in/bobpm/?miniProfileUrn=urn%3Ali%3Afs_miniProfile%3AACoAAALjq2AB-bg-_ZciitoOdgL51SkZ3HuO9Zw], 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.

Before Product Was a Function, Lessons from Amazon’s First 100 Employees | Joshua Burgin

What did product look like before product management even existed? In this episode of Zero to One, I sit down with Joshua Burgin [https://www.linkedin.com/in/joshuaburgin/], 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/ [https://www.joshuaburgin.io/]

Scaling Multi-Billion AI Platforms at Salesforce, Adobe, and Freshworks | Sriram Iyer

Sriram Iyer [https://www.linkedin.com/in/sriramviyer/]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.