Caitlin Kennedy joined CEO in 2016 as a Job Coach for its New York City office. As a Job Coach, she worked with hundreds of CEO participants and received the National Superstar Foundation’s Veronica Award for her data-driven approach to coaching and case management. In 2018, she moved to the Legal & Compliance department where she served as Contract Associate.

In 2020, Caitlin left CEO to attend Vermont Law School, where she completed its Accelerated J.D. program while also connecting justice-involved Vermonters to local reentry and social services as a Schweitzer Fellow. After a year clerking for the Vermont Judiciary, Caitlin returned to CEO in 2023 as an Assistant General Counsel with a focus on regulatory compliance and employment law.