Following high school, Shipp attended the University of Notre Dame and played four seasons there, scoring 23 goals and tallying 24 assists in 83 matches.
Throughout Notre Dame's college cup run, there was much discussion whether Shipp would be eligible for the MLS Superdraft, or could be signed to a homegrown contract by the Chicago Fire.
[6] On December 22, 2016, Montreal traded Shipp to newly crowned MLS Cup champion Seattle Sounders FC in exchange for allocation money.
He had been accepted to the program during the league's suspension for the COVID-19 pandemic but halted his announcement while serving as a team representative for the MLS is Back Tournament.
After retiring, Shipp enrolled in Northwestern University's Kellogg School of Management, where he received his Master of Business Administration in June 2022.