[3] In 2003, Gribbon moved to New York City to pursue a career in art, where she briefly worked as a cocktail waitress and a color technician for artist Jeff Koons.
[3][7] From October to November that year, her debut solo show Empty Paintings and Imaginary Sculptures was exhibited at the Sarah Bowen Gallery in Williamsburg, Brooklyn.
[3][8] In 2010, Gribbon and writer Julian Tepper founded the Oracle Club, a literary salon and artist workspace in Long Island City.
[12] After graduating, Gribbon's work largely focused on the exploration of queer identity and sensuality, and she has received positive reviews for her intimate depictions of women and gender in various solo shows.
[17][18] In 2021, her paintings appeared in a two-person show at Sim Smith Gallery, alongside the films of Agnès Varda, who Gribbon has cited as an inspiration for her work.
In her introduction for the 2023–24 exhibition Jenna Gribbon: The Honeymoon Show, at the Lévy Gorvy Dayan Gallery,[13] curator Alison M. Gingeras wrote:Her paintings demonstrate how a muse can also be a full-fledged subject, as opposed to a one-dimensional object of desire, and that looking as well as depicting can be an ethical, equitable exchange, and that desire or love can be conjured reciprocally without recourse to objectification, an ethos similarly articulated in [Celia] Paul's Self-Portrait.
[12][3] In 2017, Gribbon met American singer-songwriter Mackenzie Scott (known professionally as Torres) at a bar in the East Village,[3] and by 2019, they had moved into a "live-work space" in Bushwick, Brooklyn together.