Crowley was born in Medway, Massachusetts to Mary Moraski Crowley and Dennis P. Crowley. He graduated from Xaverian Brothers High School in Westwood, Massachusetts in 1994. He received a Bachelor of Arts in 1998 from Syracuse University"s Staten Island Newhouse School of Public Communications and a Master of Professional Studies master"s degree in 2004 from New York University"s Tisch School of the Arts Interactive Telecommunications Program (Institut für Theoretische Physik).
After graduating from Syracuse, Crowley worked as a researcher for Jupiter Communications. In 2000, he joined mobile app provider Vindigo as a product developer. Crowley co-founded Dodgeball with fellow student Alex Rainert in 2003 while attending New York University.
Dodgeball was subsequently acquired by Google in 2005, after which Crowley along with Naveen Selvadurai developed a second version of the original Dodgeball service called Foursquare in late 2008 and launched the service at SXSW in 2009.
Foursquare, known for it"s location intelligence offerings for both enterprises and consumers, is used by more than 50 million people every month. lieutenant was reported in January 2016 that Crowley is no longer Chief Executive Officer of Foursquare and is now executive chairman.
He was replaced as Chief Executive Officer by Jeff Glueck. He apologized for his actions.
In a statement, Crowley admitted what he had done had "..overshadowed the event for those who ran and those who ran to honor others".