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Cliff Wenn
Director of Squash and Co-founder
Coach Cliff Wenn brings more than 40 years of experience helping players grow through squash—whether they are just starting out or working toward competitive goals. He is certified at the highest coaching levels, including WPSA Pro Level 1 (highest of 5 levels), US Squash Level 3 Coach, US Squash Pro Affiliate, and US Squash National Verifier. Cliff holds a B.A. in Economics from Tufts University and an M.S. in Sports Management, magna cum laude, from Northeastern University.
Cliff grew up in India, Singapore, and Malaysia, where he learned the game in a strong international coaching environment that emphasized fundamentals, discipline, and smart play. Those early experiences shaped his coaching philosophy and continue to influence the LearnSquash Pathway today. He has trained and played with many elite international players and spent five years as a training and sparring partner to a former Malaysian National Champion.
Over the past four decades in the U.S., Cliff has coached players at every stage of development. He has served as Head Professional at several Boston-area clubs and was Head College Squash Coach for ten years at Tufts University and Wellesley College. He is also the long-time Squash Director at the Maugus Club in Wellesley.
At LearnSquash, Coach Cliff leads a clear, age-appropriate pathway—Foundation, Performance, and High Performance—designed to meet players where they are and help them progress at the right pace. Early stages focus on strong fundamentals, confidence, and enjoyment of the game, while advanced stages support motivated athletes with higher training intensity, competition preparation, and goal setting. In addition to directing squash programs at The Winsor School, Cliff and LearnSquash work closely with SquashBusters Boston and operate the LearnSquash Community Club. Parents value his thoughtful communication, structured progression, and commitment to each child’s long-term development both on and off the court.
Cliff’s racket of choice is the Tecnifibre Slash 120 Control used on tour by Egyptian Pro and current world #1, Mostafa Asal. “This racket has fantastic control and ample power in a traditional closed throat design."
Szilvia Szombati
Head Coach and Co-founder
Szilvia Szombati is a US Squash–certified Level 2 Coach, US Squash Pro Affiliate, and certified referee with more than two decades of experience developing junior players. Now entering her 23rd season as Head Coach at The Winsor School and Head Professional of the Squash Center, Szilvi is widely respected for building programs that emphasize strong fundamentals, confidence, sportsmanship, and a lifelong love of the game.
Under her leadership, Winsor has become one of the strongest girls’ squash programs in the country, capturing every Eastern Independent League title since 2010 and earning national finishes as high as 5th in Division I. Her coaching philosophy closely aligns with the LearnSquash pathway, meeting players where they are, establishing sound technical foundations, and guiding motivated athletes toward higher levels of competition in a healthy, age-appropriate way.
As a player, Szilvi has represented Hungary at the European Individual Squash Championships and continues to compete at a high level locally and nationally. She is the current Massachusetts Women’s 40+ Champion, a two-time State 30+ Champion, and has held the #1 U.S. national ranking in the 30+, 35+, 40+, and 45+ age divisions. Her continued involvement in competitive play helps her relate to athletes at every stage and bring a modern, informed perspective to her coaching.
Szilvi’s racket: Tecnifibre Carboflex 125 NS V2, racket of choice of Egyptian former world #1, Nour El Sherbini. “Wonderful feel, like an extension of your hand, lots of power and control all in one racket with a slightly head heavy balance."
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