Most security playbooks weren’t built for an era where AI moves faster than policy. Rob T. Lee says the default answer of “no” is creating a far bigger problem: shadow AI — widespread, unsanctioned usage that quietly exposes organizations to risk.

Rob T. Lee — Chief of Research & Chief AI Officer at the SANS Institute — joins Wade to unpack pragmatic ways leaders can move forward without breaking things. From the “tinker/hacker” mindset that helps teams learn, to treating security like a lifeguard (not a chokehold), Rob lays out the short, repeatable moves that actually get enterprises experimenting safely: enable small experiments, create accountability partners (not mythical “AI champions”), red-team your integrations, and make governance part of the daily routine.

In this episode you’ll hear:

• Why a blanket “no” to AI creates shadow AI and greater risk.
• How to flip policy toward a cautious “yes” and act like a lifeguard, not a jailer.
• Practical training tactics: 30 minutes a day, micro-projects, and hackathons.
• What good AI governance looks like — rules of acceptable use, vendor checks, red teams, and regulatory thinking.
• Why executives and boards need to be hands-on learners, not just hire an “expert.”
• The origins and purpose of the SANS Secure AI Blueprint and how to use it to align strategy, governance, and operations.

Guest: Rob T. Lee — Chief of Research & Chief AI Officer, SANS Institute

Most enterprise AI talk sounds great in theory—until you try to make it work across 40 disconnected systems. Jason Cottrell says that’s exactly where the real wins are hiding.

As CEO of Orium (and the new president of the MACH Alliance), Jason has seen what happens when companies stop chasing one big AI solution and start stacking small, composable ones. The result? For one retailer, a 9-month transformation that led to 5x digital growth—and a repeatable roadmap any enterprise can follow.

In this episode, Jason and Wade unpack why “many agents, many jobs” beats the mythical all-knowing AI, how interoperability is quietly rewriting retail, and the cultural shifts that make automation actually stick.

Grammarly didn’t just change its company name—it changed the story of AI.
In a deep-dive conversation following the company's rebrand, Superhuman CEO Shishir Mehrotra joins Zapier CEO Wade Foster to unpack why this move signals a seismic industry shift: AI is moving from tools you have to remember to use to infrastructure that works wherever you do. Superhuman’s “AI superhighway” already makes 100 billion LLM calls a week, running across over 1 million apps and websites where work happens.
Shishir shares how Superhuman Go—the company's proactive AI assistant—turns intention into execution, how to run four products as a “compound startup,” and why the next frontier of AI-driven productivity won’t look like traditional software at all.
A rare glimpse into a monumental shift—from AI as a product to AI as the plumbing of modern work.

What happens when AI meets 10 years of enterprise data?

Box CTO Ben Kus joins Zapier CEO Wade Foster to dig into how enterprise AI actually works when scale, security, and governance aren’t optional. They explore what happens when agents start reasoning across real customer data—and why the hardest part isn’t the model, it’s everything around it.

Ben shares how Box is teaching AI to work with human workflows, not against them, while Wade connects it to the shift he’s seeing inside automation: from “set it and forget it” to systems that think alongside you.

Because in the enterprise, AI has to earn trust before it scales.

AI that sells, reasons, and closes like your top rep? It sounds terrifying—but it’s not. Amanda Kahlow’s Superhumans are proving that automation doesn’t erase people; it elevates them. Her team rewards employees who replace their own jobswith AI by promoting them, not firing them. And her customers? They’re seeing sales cycles shrink from 22 days to 2 and average deal sizes double.

In this episode, Zapier CEO Wade Foster and Amanda dig into what “AI-led growth” really means—and why the smartest move in 2025 isn’t resisting AI, it’s learning how to lead with it. They unpack why 76% of 1Mind’s pipeline now comes from their own AI, and how org charts are evolving around a new role: the agent manager.

It’s a grounded, surprisingly human look at the future of work—and a reminder that the best way to stay relevant is to build the AI version of your best self. As Amanda puts it: “Your sellers hallucinate—AIs do it less.”

For Chris Pedregal, CEO of Granola, AI isn’t about replacing thinking—it’s about deepening it. He joins Zapier CEO Wade Foster to talk founder-to-founder about what it takes to build products that think with you, not for you. Together they explore why it’s the best time in history to be a builder, how AI can eliminate busywork without erasing human judgment, and why context will define the next decade of AI.

From living on the bleeding edge to running their own company on Granola, this is a masterclass in building AI that actually makes people smarter.

Replit’s mission: turn 100 million people into builders. CEO Amjad Masad joins Zapier CEO Wade Foster to discuss the real blocker to AI adoption—creativity, not code—and how enterprises can unlock it. They cover why most users freeze at the prompt, how social contagion drives adoption, and why your next “employee” might be an AI agent sitting in Slack.

What does it take to reinvent a billion-dollar SaaS company in the age of AI? For Intercom, the answer was refocusing the business, betting everything on an AI-first future, and a $50 million pricing model gamble. In this episode, co-founder Des Traynor pulls back the curtain on the bold moves that reset Intercom’s trajectory and turned its AI agent, Fin, into a powerhouse that resolves 65% of customer conversations. If you’re leading AI transformation, this is the playbook: how to make the painful cuts, how to reset culture, and how to price AI in a way that actually works. It’s not theory—it’s the story of one of the biggest AI reinventions in SaaS.