After graduating from college, she began performing at the
Upright Citizens Brigade Theatre. She is a cast member of UCB's flagship show Asssscat. Holland is a member of the comedy improv group Wild Horses, along with
Lauren Lapkus, Erin Whitehead, and
Stephanie Allynne. In 2022, she made several surprise appearances across the U.S. with the "
Ben Schwartz and Friends" long-form improv show. In 2015, Holland was cast in the
Starz series
Blunt Talk, playing Shelly Tinkle until the series' cancellation after two seasons. In 2016, she was cast in a recurring role on the
HBO series
Veep and in the film
Unicorn Store. On February 28, 2017, Holland was cast in the
ABC comedy pilot
Household Name alongside
Carol Burnett. On July 26, 2020, Holland participated in the Sequester: Undercover Mini in which she played as the Lemon. All donations for Holland's participation went to the Black Trans Travel Fund. Also in 2020, she guest starred in the final episode of season ten of
Curb Your Enthusiasm. In 2022 she portrayed principal Martha Reiser in
Senior Year, a comedy movie produced by
Rebel Wilson. The movie received generally negative reviews but Holland's performance was praised. In 2026 Holland was cast in the
Netflix series
Little House on the Prairie. ==Filmography==