Dayle Berry-Whitlock

Dayle Berry-Whitlock is a Senior Development Officer for Middlebury College with over 26 years of experience, specializing in forging principal gift partnerships and successful alumni and friend engagement strategies. 

Dayle joined the Middlebury team in 2025 and supports alumni and parents in New York City, Connecticut, and the greater Washington D.C. area. Prior to that, she developed and launched the inaugural Friends Philanthropy program at Yale University, serving as the lead strategist for the $150 million gift that made the then-Yale School of Drama tuition-free in perpetuity. Dayle has held key positions and advisory roles at institutions including the Massachusetts Institute of Technology (MIT), Columbia College Chicago, and the ASU Foundation. 

Outside of work, Dayle is a classical musician, enjoys hiking with her husband, Sterling, and is a hobby grower and volunteer for the Connecticut Food Bank.