In Episode 10 of Thriving in Ambiguity, I sit down with Jason Hebbe, former Deputy CIO for the Commonwealth of Pennsylvania, to talk shop about what it really takes to lead IT in state government.

We cover everything from:

• Multi-cloud strategies that actually work
• How to rein in rogue tools across agencies
• Why partnerships fail (and how to fix them)
• Smarter ways to navigate RFPs and procurement
• Building trust to avoid shadow IT
• Where AI and cybersecurity are headed in public sector tech

Jason brings over 30 years of IT experience to the mic, and this one is packed with insight you can use immediately.

Time

Topic

0:00:00

Intro + Jason Hebbe’s Public Sector Journey

0:03:28

Motivation Behind Serving in Government IT

0:06:56

Aligning Technology with Business Needs

0:09:42

Streamlining Statewide IT and Tool Consolidation

0:12:29

Driving Communication and Change Across Agencies

0:15:15

Avoiding Shadow IT Through Inclusion

0:16:38

Enterprise Contracts and Budget Optimization

0:18:43

Avoiding RFPs with Smarter Procurement

0:20:48

Best Practices for Multi-Cloud and Hybrid Strategies

0:25:39

Cloud Native vs. Lift-and-Shift

0:29:07

How Partners Can Bring Real Value

0:33:59

The Role of Cybersecurity and AI Over the Next 5 Years

0:38:08

Clean Data and Governance for AI Success

0:43:00

Final Thoughts and Career Advice from Jason Hebbe