She is a former member of the Upright Citizens Brigade Maude team Peaches and an original cast member of The Second City New York’s inaugural house sketch team, NYCO. While with NYCO, she performed weekly in The Best of The Second City and understudied the theater’s Mainstage company.

Winnie’s sketch group One Bad Egg performed a sold-out run at the San Francisco Sketchfest before bringing the show to Los Angeles for another sold-out performance at The Elysian Theater.

She is currently touring her solo comedy show, “@Jenna,” across New York and Los Angeles theater venues, and is performing the show at the Edinburgh Fringe Festival 2026 for the month of August. The comedic and poignant coming-of-age show features original journal entries about how the character Pam Beesly from the TV series The Office became Winnie’s gay awakening at age eleven.

“@Jenna” received rave reviews from the Brooklyn Daily Eagle and was featured in Time Out Magazine.