Gary Cunningham

Gary Cunningham


As Chief People Officer, Gary Cunningham leads Flywire’s global people and culture functions, including talent acquisition, learning and development, people operations, employee experience and wellness.

Cunningham has over twenty years of leadership experience in employee development and human resources related functions, including most recently at Waymo (an Alphabet subsidiary), where he led people and recruiting operations. Prior to Waymo, Gary spent over eight years at Oerlikon, a global engineering and manufacturing organization. There he was Vice President & Global Head of HR for one of Oerlikon’s largest divisions,  where he led diversity, equity, inclusion and culture initiatives, talent acquisition and management, performance management, international merger and acquisitions, and employee integration. 

In addition to his professional roles, Gary has held Board of Directors and membership roles in organizations including Affinity Insurance, the AIDS Foundation of Chicago, Society of Human Resource Management, and the Human Rights Campaign. Gary holds a Bachelor’s Degree from Texas A&M University and a Master Degree from North Park University, and has completed his executive education at Harvard Business School.

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