Gary Cunningham

As CPO, Gary Cunningham leads Flywire’s global people and culture functions.

Cunningham has over twenty years of leadership experience in employee development and HR-related functions, including most recently at Waymo (an Alphabet subsidiary), where he led people and recruiting operations.

In addition to his professional roles, Gary has held Board of Directors and membership roles in organizations like Affinity Insurance, the AIDS Foundation of Chicago, SHRM and the Human Rights Campaign.