Stirling, the Medfield, MA native, played prep school hockey at Salisbury School before heading to Hobart College. At Hobart, Stirling was a 4-year letter winner in both Hockey & Baseball, captaining both sports his senior year, and gaining All-American status in baseball.
Stirling has spent the last 21 years building an impressive hockey resume. Stirling's hockey background includes coach stints in youth hockey, college hockey, pro hockey and most recently junior hockey. In six seasons as a head coach in the junior hockey ranks, Stirling has successfully placed over 90 hockey players in NCAA Colleges, Tier I and Tier II USA Hockey junior programs. Currently, Stirling is an NHL scout with the Ottawa Senators.
Stirling resides in Milton, MA with his wife Lisa, and Daughters Keaton and Kendall.