Bill Pescatello

Bill Pescatello
Freshman Head Coach; Varsity Assistant Coach, Defensive Backs

Bill Pescatello leads the New Canaan freshman football program as head coach and defensive coordinator, while assisting the varsity staff as a defensive backs coach and scouting and analytics. Bill grew up in New Canaan on Putnam Road, where he tricked his grandmother into signing him up for football at the youngest age allowed and never looked back — going from a freshman-year bench player to a two-way starter by his senior year. He went on to Northwestern University, where he earned a BA, played rugby, and was named a Chicago Area Collegiate All-Star, before graduating with honors from the University of Chicago Booth School of Business.

Bill spent the last 14 years in Chicago as a general partner helping build two venture capital firms. In 2020, he returned to football as a coach at DePaul Prep, where he was part of a staff that brought home the school’s first Illinois State Championship in over 50 years. In 2025, Bill and his family moved back to New Canaan, so they could be closer to their family and go all in on coaching. He brings the same analytical, preparation-first mindset from his venture capital career to the program, building a culture grounded in effort, accountability, and preparation.

Off the field, Bill is a longtime distance runner with 10 marathons to his name (still one behind his Dad), spends too much time at the Y, and tries to be guided by his Catholic faith. He lives in New Canaan with his wife Ana and their three boys, Edward, Henry, and Michael.