Most companies are scrambling to figure out AI. Wistia did the hard part first — a total culture reset that made a 188-person company operate with the efficiency of a 30-person startup. Then AI poured gasoline on it.

Chris Savage co-founded Wistia nearly 20 years ago, grew it to serve hundreds of thousands of businesses, and took on $17 million in debt to buy out investors and stay independent. He joins Wade Foster to unpack what it actually takes to rewire a company's operating system — and why doubling headcount didn't make them ship any faster.

One mandate changed everything: ship value to customers every two weeks. Features that had been sitting on six-month roadmaps launched in two weeks. Wistia went from 12 major product updates a year to over 100 — same team size. Chris explains why the bottleneck in software is shifting to taste, how Wistia's new agentic video editor Remix is turning 45-minute sales calls into 3-minute shareable highlights, and what the "ChatGPT moment for video" means for trust in the workplace.

Plus: Wade and Chris riff on Block's AI-driven layoffs.

Linked Resources

1. Chris Savage on the Economics of AI Avatars (Sacra)
2. Wistia "Complete Control" — AI-Generated Ad Campaign Deep Dive
3. "The ChatGPT Moment for Video" — Chris Savage on LinkedIn
4. Wistia
5. Chris Savage on LinkedIn

Product and leadership roles are changing—and “PM is dead” still holds. Claire Vo, CEO of ChatPRD (100,000+ users) and former CPTO at LaunchDarkly, Color Health, and Optimizely, joins Wade to talk about what that means for how you show up: as a leader driving adoption or as someone deciding whether to lean in.

They cover why CEO "AI Mandates" and headcount freezes don’t move the needle—and what does.

Claire shares how she frames AI as career development for skeptics, the rituals that actually stick (AI Fridays, hack weeks, “no lanes”), and why executives have to get hands-on themselves (“era of the hard skill”). She gives concrete ways to start if you’re rusty: the Sunday Scaries Zapier agent, vibe coding a prototype, exec hackathons—and why leader vulnerability makes it safe for everyone to experiment. They also talk about making space for ideas at every level (dogfooding, the “cringe” channel, trading certainty for ambition), what the future product role looks like, and why hiring for willingness to learn and fearlessness about tooling beats tenure. Claire walks through how she’s building ChatPRD with fewer humans—where she’s not constrained and where she still invests in people—as a lens on how work is shifting.

In this episode, you’ll hear:

- Why “PM is dead” still holds and what the skill of the future looks like for product and leadership.

- What actually drives AI adoption—and why CEO edicts don’t.

- Why execs’ jobs are changing too and where to start if you’re embarrassed or rusty.

- How to create an environment where ideas can come from anywhere.

- Why leaning in now is a career move and what hiring looks like when adaptability and tooling matter more than tenure.

- How one AI-native company is built: where humans still matter and where they don’t.

Guest: Claire Vo — CEO & Founder, ChatPRD. X: @clairevo.

Most companies wait for their tech team to lead AI adoption. At Howard Hughes, the push started from the CFO's office.

Carlos Olea spent decades mentally cataloging process inefficiencies — as an auditor, he'd spot problems he had no authority to fix; as a finance leader, he'd hit budget or technology walls. When AI broke through both barriers, he pulled out his backlog and started building. His first project? A tool that parsed vendor bids to surface the best value — not just the cheapest price. That small win opened the door to automating lease abstraction, a notoriously manual process in real estate, with higher accuracy than humans.

Carlos talks about the risks of being a "very different CFO," why imagination — not tools or budget — is now the real bottleneck, and how he assembled a tiger team that moves at startup speed inside a public company. His playbook for winning over skeptics: fix the tasks everyone hates first.

- Why a CFO — not a CTO — became Howard Hughes' AI champion

- The decades-long efficiency backlog that finally found its tools

- How to pitch AI to your board when you don't have a tech background

- Why chasing every new model is the fastest way to accomplish nothing

- Building a tiger team that blends enterprise rigor with startup speed

Carlos Olea — Chief Financial Officer, Howard Hughes Holdings. A CPA-turned-AI-builder who led the company's first AI investments and now runs its innovation push from the finance function.

Howard Hughes Holdings: https://www.howardhughes.com/

Carlos Olea on LinkedIn: https://www.linkedin.com/in/carlosolea/