Crosby is the President of Cooperative Services, LLC and is on the Board of Directors for the Fire and Emergency Manufacturers and Services Association (FEMSA). He currently works with Sourcewell to lead their public safety cooperative procurement initiative. Formerly, he served as the President of a national cooperative procurement organization and served on the Board of Directors for the National Cooperative Procurement Partners (NCPP).

He has held several leadership positions in public safety association management including Director of Professional Development for the International Association of Fire Chiefs (IAFC). His local government career began in the fire service where he served as a fire department chief officer and project manager for city administration.

Crosby received a Bachelor of Arts (BA) degree from the University of Virginia, a Master of Public Administration (MPA) degree from Virginia Tech, and completed the four-year National Fire Academy Executive Fire Officer program.