AI is changing cybersecurity on both sides of the equation, giving attackers new ways to scale and personalize attacks while giving cyber teams new tools to defend the enterprise.

In this episode of The ProSearch Pivot, Lori Jennings sits down with Sean Stelzer, CISO and VP of Cybersecurity at Dominion Energy, to talk about the rising stakes of cyber leadership in the age of AI.

Sean shares what is changing inside cyber teams, why cyber roles are becoming increasingly specialized, why experienced talent remains so difficult to find, and how Dominion is building and retaining its cyber pipeline. They also discuss what it takes to pivot into cybersecurity, why moving into cyber leadership has become more difficult, and what executives and boards should be paying attention to as the threat landscape continues to evolve.

The Rising Stakes of Cyber Leadership: AI, Board Pressure, and the Talent Needed to Defend the Enterprise

Dean May was a Senior Director of Platform Engineering at Capital One when he emailed a recruiter about a job several levels below him — less money, smaller title, individual contributor.

That recruiter was Lori Jennings, and she almost talked him out of it.In episode one of The ProSearch Pivot, Dean explains why he walked away: his LinkedIn said he coded every day, but he was really writing PowerPoints, and he could feel his technical skills eroding right as a wave was forming.

He let the job go, took a 15-month sabbatical, traveled, invested in startups, and spent six months in UC Berkeley's AI/ML immersion program rebuilding his hands-on skills. He now advises roughly 30 Series A and B startups at the CTO and CEO level through AWS Startups.

From there the conversation opens up into what he's seeing across dozens of companies:

- The true total cost of AI ownership, and why "cheaper than a human" is falling apart

- Why the specialist is losing value and the generalist who understands the business is winning

- The rise of the player-coach leader who can still do the work

- What happened when interns demoed a finished product and couldn't name the stack they'd built it on

- How to start building these skills if you're several layers below the executive suite

There's also one moment worth the whole episode. Dean's therapist asked him a single question that made the leap possible: how far could you really fall?

The ProSearch Pivot is hosted by Lori Jennings, founder of Jennings ProSearch. https://www.jenningsprosearch.com/