Flynn began his career as a law clerk to the Honorable Justice Henry duPont Ridgely before becoming a litigation associate at Richards, Layton, and Finger. His interest in public service led him to Washington, DC where he headed the Equality PAC, Congressional LGBT Equality Caucus, and served as Chief of Staff for Congresswoman Mary Gay Scanlon prior to joining the NTIA.

A native Delawarean, Flynn received his B.A. from American University and his J.D. from Washington & Lee University School of Law, where he was Burks Research Scholar and the recipient of the Calhoun-Bond Award.