After working as residence manager at the University of Guelph, and as MPP Liaison for the Minister of Citizenship, Culture and Recreation, Coolman joined the University of Waterloo as residence life coordinator in 1999.

In 2000, as Waterloo embarked on a $600+ million campaign, Coolman joined the Office of Development, where he held roles as development officer, annual fund and development officer, major gifts & corporate campaigns. He assumed the role of director, Alumni Affairs in January of 2005 and was promoted to associate vice-president, Alumni Relations in 2013.

Coolman completed his master's degree in leadership at the University of Guelph. His major research project entitled, "The Science Behind the Art of Engaging Alumni: Linking Engagement and Impact" utilises alumni research data to build a strategic advancement model.

Coolman has presented his research and other advancement related topics at conferences in Canada, USA, and Europe. He is the author of several feature articles on the topic of alumni engagement. His professional accomplishments earned him the 2011 Rising Star award from the Council for Advancement and Support of Education District II (CASE).