A decisive voice for leaders navigating the digital economy

Jason Cummings is an enterprise technology strategist and trusted advisor to executive teams navigating the complexities of the modern digital economy. As the founder of Empowerment Strategies, he partners with senior executives and leadership teams to build the readiness organizations need before committing to technology decisions.

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 and 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 and legal clients, and leading a team that modernized internal reporting for one of the nation's largest 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 on the Board of Directors of the nonpartisan Civic Federation and holds leadership roles within the Economic Club of Chicago and the University Club of Chicago.

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.