A decisive voice for leaders navigating the digital economy

Jason Cummings is an enterprise technology strategist and trusted advisor to leadership teams facing consequential technology decisions. As the founder of Empowerment Strategies, he partners with decision-makers to build the readiness organizations need before they commit.

His perspective is shaped by more than twenty years spent between hands-on execution and executive advisory work. As an AI & Cloud Strategic Executive at Google, he drove cloud adoption strategy across government and higher education, including Chat with CTA, the Chicago Transit Authority's applied intelligence modernization that expanded rider access and customer service capacity. As a consultant, he delivered a modernized budgeting platform for the City of Chicago, fully tested and ready for go-live, and delivered a custom tracking and audit system for the Cook County Clerk's Office. His work has also spanned international due diligence for a major automotive restructuring, finance transformation for healthcare clients and procurement transformation for legal clients, and leading a team that modernized internal reporting for one of the nation's largest customer-owned health insurers. He held finance and risk roles at Bank of America and Ernst & Young.

An engineer by training, Jason still likes to build, tinkering with new tools in his own time.

In public life, Jason serves as Vice Chair of the Board of Directors of the nonpartisan Civic Federation, where he also co-chairs the Governance and Nominating Committee. He holds leadership roles within the Economic Club of Chicago and the University Club of Chicago, including service on the University Club's Admissions Committee.

He holds a Bachelor of Science in Interdisciplinary Engineering from the University of Michigan, an MBA in Finance from Clark Atlanta University, and an Executive Certification in Digital Business Strategy from the MIT Sloan School of Management.