How to Avoid AI FOMO like Patagonia | Angela Clark, VP Digital

March 24th, 2026  |  Season 2  |  30 mins 42 secs

business, digital experience, product management, technology

I keep meeting teams across the country that are facing intense pressure to shoehorn AI into every feature, often without a coherent thesis on the problem it’ll solve. But what if the smartest move in the AI gold rush is to actually slow down?

Angela Clark, VP of Digital at Patagonia, is doing exactly that. At a brand known for its fierce commitment to the planet, Angela is applying that same intentionality to their digital experience. Instead of blowing budgets on every new AI tool, she’s taking a thoughtful approach to building a personalized customer journey across an audience that spans both elite pro athletes and weekend warriors.

In this episode, Angela shares:

• How her team is designing a customer journey that caters to the buyer on a 1:1 level, including Product Detail Pages that can speak effortlessly to either extreme of their customer base
• Her playbook for managing AI-related “shiny object syndrome" and keeping your roadmap focused on the customer.
• And why Patagonia flipped the definition of “customer lifetime value” to align with their conservation-driven mission — even happily downselling you to a refurbished item instead of a newer, more expensive version.

The Anti-Headcount Billion-Dollar eCom Playbook | David Cost, CDO (Rainbow Shops)

March 17th, 2026  |  Season 2  |  26 mins 57 secs

business, digital experience, product management, technology

How many engineers does it take to run the ecommerce site for a retail company that does over a billion dollars in revenue per year?

Well, if you’re Rainbow Shops, the answer is just 2.

Most ecommerce teams assume scale requires more engineers, more tools, more complexity. Chief Digital Officer David Cost has built something many people in ecommerce would say isn't possible — a lean, fast-moving digital operation that runs on vendor partnerships instead of a massive internal team. Two engineers, hundreds of programmers' worth of output, and none of the overhead that comes with scaling the traditional way.

In this episode, David shares:

• A detailed, under-the-hood look at the specific vendors they use to stay so lean
• His playbook for using strategic partnerships with vendors as an external dev team
• How being a testbed for new tech gives them a competitive edge
• And why their choice of ecommerce platform was vital in enabling Rainbow’s digital strategy

The World’s Safest Driver Isn’t Human. Can Waymo Stop Traffic Deaths? | Chinmay Jain, Dir. Product

March 10th, 2026  |  Season 2  |  24 mins 53 secs

business, digital experience, product management, technology

40,000 people a year die from traffic accidents in the US. Our guest today is Chinmay Jain, Director of Product Management on Waymo's Driving Behavior team, who is working to make that number 90% smaller.

In this episode, Chinmay shares:

• How he thought through leaving YouTube at its peak to join a moonshot company that could have civilization-level impact
• Waymo’s actual AI eval process, using massive simulations based on millions of real-world driving miles to maximize edge cases, ultimately turning trust into their real product
• And the misleading, but common, metrics Chinmay and his team learned to spot that could have seriously derailed Waymo’s progress

The Cortisol UI: How We Fix FinServ’s Empathy Problem | Melissa Douros, CPO (Green Dot)

March 3rd, 2026  |  Season 2  |  32 mins 14 secs

business, digital experience, product management, technology

Most financial products are optimized for transactions, not human emotion. For many people, this transforms an already fraught topic into pure anxiety.

Our guest today is building banking for what she calls the Cortisol UI.

Melissa Douros has spent over 26 years in financial services, starting in debt collection and now serving as the Chief Product Officer at Green Dot. Early on, she learned firsthand that shame is a terrible retention mechanism. That lesson now shapes how she builds financial products for millions of users — for whom the time spent simply navigating their finances can be the most stressful of the day.

In this episode, Melissa shares:

• How finserv companies can design for the “Cortisol UI“ by building trust and experiences that reduce anxiety before the transaction
• An experiment she ran for Discover’s 5% cashback program where test users collapsed under decision paralysis — proving that more choice can actually increase financial stress
• How she flipped Great Wolf Lodge’s booking model from 70% call center to 90% digital while enhancing the human experience
• AND how Green Dot is navigating AI and agentic commerce without breaking the one thing banks can’t afford to lose: trust

The $500M Lesson from Amazon’s Homepage Redesign | Rahul Chaudhari (ex-Amazon, Kohl’s)

February 24th, 2026  |  Season 2  |  33 mins 55 secs

business, digital experience, product management, technology

How do you redesign the most visited e-commerce webpage in the world? Rahul Chaudhari helped reshape the Amazon homepage during his years as a product leader there, before becoming VP of Product and Technology at Kohl's.

In this episode, Rahul shares:

• Amazon’s “customer backwards” approach - and how he used it to unlock half a billion dollars of value on the Amazon homepage
• The secret to product adoption: leverage existing customer habits to unlock new opportunities
• And how Amazon and Google raised the bar for digital experiences so high that now every other product pays the price

Smarter AI Models Won't Fix Your Deployment | Maryam Ashoori, VP PM/Eng (IBM, Watsonx)

February 17th, 2026  |  Season 2  |  26 mins 49 secs

business, digital experience, product management, technology

In this episode, we’re joined by Maryam Ashoori, VP of Product and Engineering at IBM’s Watsonx platform. With a background that includes 2 master's degrees in AI, a PhD in Systems Design Engineering, and named on over 30 patents at IBM, she’s been on the bleeding edge for over a decade. Currently leading the charge on Agentic AI and AI Governance at IBM, Maryam is a bridge between the theoretical frontier of AI and the messy reality of enterprise deployment.

In this episode, Maryam:

• Tells why AI has been stuck in pilot purgatory for longer than expected, and what you need to do today for a successful enterprise deployment
• Calls shenanigans on the “biggest, best model” crowd, and why often a smaller, more focused tool is the right choice
• Explains how to build an agnostic architecture that can handle the realities of an AI world where models advance faster than anybody can keep up

Using AI to Preserve 140 Years of History at the LA Times | Deepika Manglani, VP Product (LA Times)

February 4th, 2026  |  Season 2  |  25 mins 13 secs

business, digital experience, product management, technology

In this episode, we’re joined by Deepika Manglani, VP of Product and Program Management at the LA Times. Deepika’s career in media spans over 15 years, culminating in her current role, where she’s bringing the 140-year-old institution into the future.

In this episode, Deepika shares:

• How her team is using AI to preserve a unique trove of historical data, over 12 million pages of news archives from as far back as the 1800s
• What this digital archive and maturation of AI enables for future storytelling, media innovation, and news personalization
• Why combining product and program management was critical to navigating massive transformation at the LA Times through a period of heavy M&A activity

Designing for Attention: How CrossFit Builds Product for Community-Led Growth | Ben McAllister, CPTO

January 27th, 2026  |  Season 2  |  25 mins 48 secs

business, digital experience, product management, technology

In this episode, we’re joined by Ben McAllister, the Chief Product and Technology Officer at CrossFit, and one of the most thoughtful product leaders I’ve had the pleasure of speaking with.

Ben’s path is anything but linear: with a degree in physics, a short stint in consulting, and time spent as a creative director at a design agency before moving into senior product roles at Under Armour. Now he’s shaping one of the world’s most iconic fitness ecosystems.

In this episode, Ben shares:

• Why attention is the ultimate currency in product design, and how to design for the “spotlight” versus the periphery.
• The “Infovore” Advantage: Why the best product leaders borrow ideas from outside the tech world; and
• How to build a cohesive product strategy for a complex, decentralized network like CrossFit’s global community of affiliates and athletes.

How AI Can Eliminate the “Chaos Tax” in Enterprise Software | Karthik Viswanathan (TalAiro)

January 20th, 2026  |  Season 2  |  28 mins 15 secs

business, digital experience, product management, technology

In this episode, we’re joined by Karthik Viswanathan. Formerly a product leader at AT&T, Macy’s, and Optum, he’s now the founder of TalAiro, an HR tech startup that is rethinking the operating system for recruiting.

Karthik argues that the hidden failure of the modern tech stack is forcing the user to serve as a “manual integration layer. He explains how the push to "unbundle" features results in a “Chaos Tax”— consuming 40-60% of the workday with fighting disconnected tools rather than doing their jobs.

Beyond that, Karthik also discusses:

• How AI can make work more human: Why the true value isn't in replacing jobs, but automating the "devil's cut" of administrative work.
• The journey from enterprise leader to founder: What building TalAiro from scratch taught Karthik about prioritization after years of leading enterprise product orgs, such as focusing on the 20% of workflows that drive 80% of the value

April Dunford’s 1 Killer Question to Expose Weak AI Product Positioning

January 13th, 2026  |  Season 2  |  36 mins 2 secs

business, digital experience, product management, technology

This week, we’re joined by the undisputed queen of B2B positioning, April Dunford.

April is the best-selling author of the seminal book "Obviously Awesome" and the new hit "Sales Pitch." She has spent 25 years as a startup executive and consultant helping companies stop guessing and start winning. If you have ever struggled to explain exactly why customers should pick you over the other guy, this episode is a masterclass.

In this episode, April talks about:

• Why Positioning is a Product Problem: How undefined positioning leads to wasted roadmaps, "not good enough" feedback from Sales, and engineering teams burning out on features that don't win deals
• The "AI Washing" Trap: Why saying "We have AI" is no longer a strategy—and how to articulate the specific value your tech unlocks that the competition can’t
• Why she loves when competitors lie: How to ethically trap competitors who over-promise features (and the one question sales should tell your prospects to ask them)
• And finally, vision vs. reality: How to sell the "glorious future" without losing the deal you need to close today