McKenney began his career as a volunteer middle and high school teacher at a Catholic school in India. In 2013, he joined Harvard University working in advancement during The Harvard Campaign. In 2017 Tom became the Executive Director at Holy Cross Family Ministries Foundation in North Easton, where he serves as the chief fundraiser and oversees the endowment. He rebuilt the advancement program and exceeded fundraising records during his four years in this role.
A graduate of Stonehill College, Tom also holds a Master of Education from Harvard University and is a Certified Fund-Raising Executive. He co-founded the Rural Education Resource Development Initiative, which provides underserved children scholarships to Catholic schools in India. He also serves on the advisory board at St. John School and as the co-chair of the development committee at the St. Oscar Romero Parish in Canton, MA.