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.