Maddie Winslow is a Director at Inner Circle Sports, William Blair's Sports, Media & Entertainment group. She joined William Blair's investment banking team through the firm's acquisition of Inner Circle Sports, where she had worked since 2021. Before Inner Circle Sports, she was at Jefferies and AGC Partners.

Within the Sports, Media & Entertainment practice, she co-leads the firm’s women's-sports coverage. She has worked with the NWSL, LOVB, Unrivaled, Gotham FC, San Diego Wave, Chicago Stars, among others. Outside of women’s sports she has worked on M&A and stadium financing deals with clients across the major men’s leagues including the San Diego Padres, Tampa Bay Lightning, Austin FC, and Minnesota Timberwolves & Lynx