Deborah Cusumano Caldwell

Debby collaborates with firm leadership to develop and implement Winston’s comprehensive alumni relations strategy and initiatives. She works closely with the firm’s business development, DEI, well-being, and professional development teams to identify opportunities to offer innovative and enriching programming to our alums. She also serves as the firm’s primary liaison to Winston alums. 

Prior to being named in 2024 as the firm’s first director focused exclusively on alumni relations, Debby served as director of partner hiring & alumni relations. She joined Winston’s attorney recruiting team in 1996 after serving in recruiting roles at two other law firms.