Product Rebels

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 ready
Why Bamboo AI was built as native agents and not a bolt-on assistant
What turned out harder than expected when shipping agentic AI
Measuring AI features by behavior change, not feature count
How the CPO role has changed, and what Brian spends his time on now
A 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.