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Cliff Wenn has a long and varied work experience. In 2022, they became the Owner of LearnSquash Community Club at SquashBusters. From 1998-2012, they were the President/Owner of Winning Sports, Inc./dba Learnsquash, where they focused on squash instruction and ran private lessons, clinics, and a summer camp series. From 2012-2018, they were the Director of Squash at CoachUp. From 1997-1998, they were the Director of Squash at The Maugus Club, where they conducted private, semi-private, and group lessons for members of all ages and was a pro shop owner and authorized dealer for all major squash brands. From 2018-2013, they were the National Sales & Marketing Manager at Eye Rackets Americas. From 2013-2018, they were the Regional Sales Manager (Consulting) / Adidas Badminton Lines at Budomart America, Inc. where they oversaw sales and marketing and assisted in sales and marketing strategy for Adidas Badminton nationwide. Lastly, from 1995-1997, they were the Head Squash Coach/Lecturer at Wellesley College, where they were in charge of all facets of the squash program, including day to day coaching, season planning, recruiting, and team management, as well as a lecturer in the physical education department.

Cliff Wenn attended Singapore American School from 1971 to 1982. Cliff then went on to Tufts University where they obtained a B.A. in Economics from 1982 to 1986. After this, they attended Northeastern University where they obtained an M.S. in Sports Management from 1988 to 1990. Additionally, they are a WPSA Certified Squash Teaching Professional, Pro 1 (Highest Level, out of 5 levels).