Sandboxes, Not Shadow AI

What happens when your team starts running customer data through personal AI accounts, and locking it down would only push them further underground?Heather Samarin sits down with Nilesh Singh, Head of Product at Unicity, a 40-year-old health and wellness company operating in 56 countries. When his team discovered PMs exporting distributor data to their own AI tools, they built a governed sandbox instead, with masked data and a dedicated AI governance role. Now PMs get directional answers in days instead of six weeks.They also get into why a PM's value now comes from domain knowledge and catching edge cases, why specs are swinging back toward waterfall when the coder is an AI agent, and why the teams that capture their decisions and context will win over the next five years.Book a free 20-minute call with Heather: https://calendly.com/hsamarin/productrebelsdiscoveryLearn about the Groundwork AI Blueprint: https://productrebels.com/productledfoundations/

Brian Crofts and I go back to our Intuit days, and we took the same unusual path into product, starting out in corporate finance. Today Brian is Chief Product Officer at BambooHR, where his team is shipping AI agents into real HR workflows. He joined our AI series to talk about what that work looks like from the inside.We start with the rebel move that shaped his career: pushing for TurboTax Live when the idea cut against how the company positioned the product. From there we get into how Bamboo AI started and the bet behind it, which is moving customers away from clicking through software and toward handing a problem straight to AI. Brian describes SaaS UX as moving from navigation to collaboration to delegation, and he's clear that we have to move at a pace customers are comfortable with.A big thread in our conversation is why AI makes product fundamentals more important. When building gets fast and easy, it also gets easier to build the wrong thing. Brian thinks we've hit a new definition of lazy, and that we have to recover the art of great insights. He also has a sharp take on leadership. CPOs no longer have the pattern recognition that years of experience used to give them, so their own curiosity and tinkering is how they give direction to teams who are learning too.In this episode:The TurboTax Live story and being right before the room is readyWhy Bamboo AI was built as native agents and not a bolt-on assistantWhat turned out harder than expected when shipping agentic AIMeasuring AI features by behavior change, not feature countHow the CPO role has changed, and what Brian spends his time on nowA new definition of success for PMs, designers, and engineers: high curiosity plus high agency

We're back with a special host-only episode! Vidya Dinamani and Heather Samarin step out of the guest chair to unpack what they're hearing across nearly twenty AI roundtables they ran with CPOs, VPs, and product leaders across the industry.Why the PRD is giving way to context, how the PM-to-engineer ratio is flipping, the pull toward a shared context layer, and why there's still no one-size-fits-all for AI.If you're a product leader silently wondering whether you're behind on all this, the genuine answer from the room is that everyone is, and that should bring you some comfort.Plus the persona skill one leader built to stop the slop.

Why do so many product transformations fail? Because leaders treat product like a science when it's mostly art.Vidya Dinamani and Heather Samarin sit down with Chris Herring, Head of Product at Stride, the edtech company serving K-12 students through virtual public schools. Chris has been building AI products for over a decade — well before it was fashionable — including StoryStudio and MathBee, the math game that helped kids find out math doesn't suck.From refusing to imitate what worked elsewhere, to piloting change with four teams before scaling to forty, to why trust is the currency that buys you permission to rebel, Chris shows what it takes to drive transformation from the inside.

What does it actually look like to run a one-day sprint cycle? To have agents building product overnight? To compress months of work into days — and still ship things that matter?Kris Kaneta, Chief Product & Innovation Officer at Norstella — one of fast company's most innovative companies of 2025 — is doing it. And in this episode, he shares how with hosts Heather Samarin and Vidya Dinamani.From the premium on clarity in an AI-led pdlc, to the difference between building to learn and building to earn, to why ai is exposing — not hiding — weak product thinking, Kris gives one of the most operationally grounded views of AI-first product leadership we've heard.

What happens when product leaders stop talking about AI theory and start sharing what’s actually working?In this special Product Rebels episode, Vidya Dinamani and Heather Samarin unpack insights from four AI roundtables with CPOs, VPs, and product leaders. They explore AI slop, ROI challenges, role anxiety, rapid prototyping, and why judgment, customer insight, and product fundamentals matter more than ever in an AI-driven world. The future of product management may be changing, but its core purpose remains the same.

What does it take to turn a struggling edtech platform into a mission-driven product powerhouse — in under a year? Vidya Dinamani and Heather Samarin sit down with Jared Harless, Chief Product and Technology Officer at BookNook, as he talks about his early days bootstrapping digital products inside a billion-dollar publishing company, to leading a turnaround that grew revenue 25% year over year and pulled customer retention from 27% to 70%...but the work is far from over. Jared gets real about the kind of conviction it takes to build before you have permission — and how going straight to the market before writing a line of code is still the most powerful move a product leader can make.

Hey there Product Rebels! If you're a product leader right now, chances are someone in your org has asked you some version of "what's our AI strategy?" in the last month. And chances are, the answer is still murky. We're hearing this from product leaders constantly — there's pressure to ship AI features, but not a lot of clarity on how to move from boardroom excitement to actual product impact.That's why we're resurfacing this conversation with Ravi Mehta. His Inspire, Validate, Structure, and Ship framework is one of the most practical takes we've heard on turning AI ambition into real outcomes. If anything, it's more relevant now than when we first aired it. Enjoy the re-listen. 

Hey there Product Rebels! We've had a lot of conversations with product leaders lately, and one thing that keeps coming up is how much financial guesswork is involved in incorporating AI into their product orgs. From forecasting costs to proving ROI, it's a challenge that really comes down to something more fundamental — do PMs actually understand the economics of the products they're building? That's exactly what Nat Kunes digs into in this episode. While the conversation isn't specifically about AI, the financial fluency he talks about is the exact muscle product leaders need right now. Enjoy the re-listen.In this episode, Heather Samarin and Vidya Dinamani sit down with Nat Kunes, Chief Product Officer at Ontra. He shares his insights on redefining pricing strategies, replacing assumptions with validated hypotheses, and the impactful strategy he uses to empower his team to balance goals with true user value. Nat digs into financial fluency for PMs, market validation practices, and shifting org culture to view product as an asset, not a liability. 

What does it mean to be a true product rebel in the age of AI? Heather Samarin and Vidya Dinamani sit down with Raviv Levi, former Chief Product & Technology Officer at Sift, as they unpack how product leaders can stay focused on what really matters—amid constant noise, data overload, and accelerating change. From building alignment across competing teams to rethinking experimentation in an AI-first world, this conversation explores how faster prototyping, sharper problem focus, and stronger conviction are redefining product leadership.