In 2005, at age thirteen, Generosa appeared in the Radio City Christmas Spectacular as Clara.[4]
After Generosa graduated, she was not offered an apprenticeship with the New York City Ballet.[5] The Pacific Northwest Ballet hired her, but had her spend several months at the company's school before allowing her to join in 2011 as an apprentice; she was taken into the corps de ballet the following year.[1] In her second year at the company, she was cast by Twyla Tharp to create a role in Waiting at the Station.[1] She was promoted to soloist in 2016.[6] Whilst in the corps and as soloist, she was already cast in lead roles, including Aurora in The Sleeping Beauty, Balanchine's Tarantella, "Rubies" from Jewels, Robbins' The Concert, and Fenley's 34-minute solo State of Darkness.[5][7]
In 2020, she danced The Swan in Misty Copeland's fundraiser, Swans for Relief, a response to the COVID-19 pandemic's impact on the dance community, with funds going to participating dancers' companies and other related relief funds.[8] Later that year, the Pacific Northwest Ballet announced her promotion to principal dancer during their first digital gala.[7]