Jay Cleary

I joined DJS to develop internal and external communication strategies and serve as the agency's primary spokesperson. In that role, I represented DJS through multiple high-profile public crises, including incidents that drew national media attention. I learned how to manage messaging under intense pressure, a skill that would prove invaluable in every role that followed. Working closely with a new agency Director starting in 2011, I became a trusted advisor on messaging strategy, drafting talking points, and representing the agency at public events. That working relationship laid the foundation for what came next.

Promoted by the Director I had been advising, I stepped into the role of Chief of Staff at Maryland's Department of Juvenile Services. I provided high-level strategic counsel to the Director, managed a portfolio of five offices and more than 70 staff, and served as the agency's representative to the Governor's office across both Democratic and Republican administrations. As one of the chief architects of the agency's strategic vision and plan, I played a central role in reforms that drove a 46% reduction in youth detention and an 80% decrease in deep-end placements. I also became the executive subject matter expert on electronic monitoring technology, working closely with the Electronic Monitoring unit and managing the agency's relationship with our GPS technology vendor.

• Provided strategic counsel to the Director across two gubernatorial administrations
• Managed five offices and a staff of more than 70
• Led executive-level crisis response for statewide technology failures
• Participated in vendor evaluation and deployment of a custom case management system
• Built an employee recognition program from the ground up that awarded over 200 staff

After leaving DJS, I brought my operational expertise to the federal level at OJJDP. This experience broadened my perspective from a single state to the national juvenile justice landscape, giving me visibility into how agencies across the country approach technology, reform, and operations. It deepened my understanding of the policy environment that shapes corrections technology purchasing decisions nationwide.

I launched Cleary Consulting to put 15 years of juvenile justice and corrections experience to work for the organizations and companies operating in this space. After earning my Certified Artificial Intelligence Consultant (CAIC) certification from the U.S. Artificial Intelligence Institute, I built a practice that combines deep operational knowledge with a structured understanding of AI strategy. Today, I provide training and technical assistance to juvenile justice agencies and national organizations, help technology companies enter the market with a strategy grounded in how these agencies actually operate, and give investors the operational perspective that no pitch deck can provide.