Six Times Private Equity IT Playbook W/Bradley Stokes - #397 (71:17)
You've Been Heard, Friday, February 20th, 2026
Bradley Stokes is a six-time private equity CIO who's perfected the art of repositioning IT from cost center to value driver. He's got a five-step playbook that works every time: goodwill tour, PMO setup, staffing assessment, data foundation, and standardization.
His approach flips the script. Instead of IT begging for budget, he shows executives 200 projects that would take 25 years to complete. "We're going to work on ten. That's the resourcing we have today," he tells them. Suddenly the business is prioritizing for him.
We get into why reporting to the CFO starts you with one hand tied behind your back, how AI is the first technology the business brought to IT (not the other way around), and why most IT leaders are stuck in "run mode" when they should be builders. Bradley's blunt: "Those days are done. We talk about solving business problems, not building Cisco infrastructure."
The payoff? A repeatable framework that works whether you're in PE or not. Because every business needs IT leaders who understand that without technology, nothing runs.