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 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.

What happens when product leaders prioritize profit over long-term value?  In this episode, Michael Nierstedt shares lessons from more than a decade building payroll and HR technology across companies like Gusto and Paylocity. He explains why product investment drives competitive advantage, why product managers must think like sellers inside their organizations, and how real influence comes from delivering value in production. The conversation also explores customer research, the realities of building AI-driven products, and why the next generation of product leaders must learn to delegate, coach, and empower their teams. 

In this special episode of Product Rebels, Vidya Dinamani and Heather Samarin revisit highlights from their recent webinar, AI as a Force Multiplier for Product Discipline, featuring product and AI leader Elena Luneva. After the live session sparked a wave of thoughtful audience questions, they sit down to tackle some of the most pressing ones—from how AI is reshaping product work to why strong product fundamentals matter more than ever.

What does great product leadership look like when you’re asked to go along with a big initiative you don’t believe in?  In this episode, former CPO at Everway, Timothy Alvis, talks about the tough calls product leaders face when conviction clashes with consensus.  From telling better stories, to embracing problem obsession over solution fixation, Tim shares hard-earned wisdom from leading at scale and navigating complex orgs. We also hear how he’s now applying AI to rethink product work itself. Whether you’re an aspiring CPO or in the trenches today, this episode offers plenty of gold.

What happens when you challenge long-held assumptions—and let real data and user behavior lead?  In this episode, Vidya Dinamani and Heather Samarin sit down with Harish Pandian, CPO at Gravity, to talk about driving product transformation in industries resistant to change.  From building gamified safety tools to rapid-fire prototype testing on job sites, Harish shares how deep customer empathy, hard data, and cross-functional trust unlock real adoption and lasting impact. 

What does it really mean to make AI practical in product teams?  In this special year-end episode, Vidya Dinamani and Heather Samarin are sharing highlights from a recent Product Rebels live webinar focused on how product leaders can apply AI in meaningful, responsible ways.  Joined by Polly Allen, former Principal Product Manager at Alexa AI, they explore grounding AI in real customer problems, aligning AI efforts to business strategy, and why leaders can’t afford to stay hands-off.  This is a candid, experience-driven conversation about judgment, risk, and leadership in an AI-powered product world.

What happens when a product leader enters a company and rewrites the strategy playbook—not with a megaphone, but with a matchstick and a campfire? Vidya Dinamani and Heather Samarin sit down with Raji Bedi, CPO at Lob, as he shares his analogies-packed approach to aligning teams, building product culture, and moving from "roadmap blur" to clarity and execution. From transforming product managers into organizational "locals", to advocating for faster cadence and fuller buckets, Raji offers a masterclass in practical product leadership.  Tune in for a memorable and energizing conversation on curiosity, collaboration, and leading with intent. 

This special episode of Product Rebels brings you highlights from a recent webinar hosted by Heather Samarin and Vidya Dinamani, and featuring product veteran Ravi Mehta. With AI hype reaching fever pitch, many product teams are being pushed to “do AI”—without clear strategy or outcomes. In this candid conversation, we break down what’s really working in teams today. Learn the Inspire, Validate, Structure, and Ship framework designed to move your team from idea to impact with clarity. If you’re a product leader navigating how to integrate AI meaningfully, this episode offers practical steps, real examples, and a refreshing no-fluff approach.

What does it really mean to be a product rebel?  Heather Samarin and Vidya Dinamani sit down with Saurabh Sharma, CPO at You.com, as he shares how asking the tough questions can shift an entire company's trajectory.  From tackling NFT theft at OpenSea to transforming product leadership with resilience, Saurabh brings real-world insight on thinking systemically, building partnerships, and elevating PM influence.  Learn how he uses "relentless subtraction" to stay focused, why RQ matters just as much as IQ, and how understanding your stakeholder's language can unlock big wins. 

How do you drive lasting change in one of the most complex and high-stakes industries—healthcare?  Vidya Dinamani and Heather Samarin sit down with Nasir Ali, former CPO at CareMetx, to explore how a product mindset can reshape legacy systems.  From shifting to scalable solutions to outcome-based contracts, Nasir shares real-world tactics and lessons in driving innovation at scale.

What does it take to drive product innovation across cultures, languages, and business units? Heather Samarin and Vidya Dinamani sit down with Chris Pasley, former VP of Product at 17Live, as he shares lessons from scaling product at a global live-streaming platform. From managing incentives in a “whale economy” to aligning cross-country OKRs, Chris shares stories of stakeholder wrangling, cultural empathy, and staying true to the customer. He also offers a practical framework for defining MVPs and driving impact through problem-cause-solution thinking.

What does it take to build products that transform not just classrooms, but the entire education space?  Heather Samarin and Vidya Dinamani sit down with a product leader who's done just that—Rachel Stack, Chief Humanities Officer at Great Minds. From navigating complex nonprofit-to-for-profit transformation, Rachel shares how her teams embraced continuous learning, prioritized with discipline, and preserved the "special sauce" of mission-driven education.  Explore real talk on product structure, educator-led development, value stream mapping, and how to lead with curiosity while staying grounded in purpose. 

What does it take to push back against the status quo—and win?  Vidya Dinamani and Heather Samarin sit down with Colt Stander, CPO at Presence, as he shares what it means to be a true product rebel.  From tackling overlooked customer problems to navigating leadership resistance, Colt reveals how his teams tested controversial ideas and drove innovation in hardware and healthcare. He offers honest insights on product storytelling, user obsession and why the best PMs challenge assumptions. 

How do you scale product impact while keeping customer trust at the center? Heather Samarin and Vidya Dinamani sit down with Ismail Elshareef, CPO at CarGurus, as he shares his bold approach to leading with empathy, optimism, and integrity. From standing up against revenue-first tactics to cultivating teams that challenge norms with courage and candor, Ismail brings tactical advice from hard-earned wisdom.  Tune in to hear how he develops customer-obsessed teams, asks the right questions, and stays relentless curious—even in high-stakes environments.