2010s In 2010, Gentili began an internship at
The LGBT Center, where she began working with the NYC Anti-Violence Project. From 2012 until 2016, she was the trans health program coordinator at the
Apicha Community Health Center in New York City. From 2016 to 2019, Gentili was the Director of Policy at the
GMHC, an AIDS service organization in New York City and the world's first organization dedicated to HIV/AIDS prevention. While part of the GMHC, she advocated for the
Gender Expression Non-Discrimination Act (GENDA), a proposed piece of state legislation which was eventually signed into law in 2019. In 2019, she also founded Trans Equity Consulting, a development consulting firm that sought to center trans women of color, immigrants, sex workers, and incarcerated people. That year, she also joined the Board of Directors of Stonewall Community Foundation, a New York-based, LGBTQ-focused grantmaking organization, where she served until her death. The services provided by Trans Equity Consulting include workshops and trainings, organizational developments, conference and convening planning, speaking and story telling and conflict medication. Through workshops and trainings, Gentili has trained individuals ranging from government to non-profit and academic settings on subjects such as LGBTQ competency, policy, transgender care, and sex worker issues. In 2019, Callen-Lorde honored Gentili with their yearly Community Health Award for her contributions to the visibility and health of the LGBTQ+ community, recognizing her leadership and also for her partnership with Callen-Lorde.
2020s In 2020, she hosted
Fierce Futures, a fundraiser supporting organizations that aid Black trans people. In 2021, Gentili was a co-founder of
Callen-Lorde Community Health Center's "Cecilia's Occupational Inclusion Network" (COIN) clinic, the first dedicated healthcare center for sex workers on the East Coast. The COIN Clinic provides their patients with access to various essential services. Some services include primary care, sexual health, behavioral health, dental access, pharmacy and more. They work diligently to provide care not only for those with health insurance but also those who are uninsured. As a result, their mission is to provide those who identify as sex workers free care in a supportive environment. In January 2022, she was one of several community leaders who sent a letter asking Governor
Kathy Hochul to create the
Lorena Borjas Trans Equity Fund. In 2022, she was a finalist for The David Prize where she was recognized for her effort to make New York a more inclusive city for transgender and sex worker rights. In February 2023, she was one of hundreds of
New York Times contributors who signed a letter condemning
the newspaper's coverage of transgender people. In October 2023, she was among hundreds arrested at a protest in
Grand Central Terminal calling for a
ceasefire in Gaza organized by the anti-Zionist organization
Jewish Voice for Peace. == Creative pursuits ==