Rae Caballero Obejero is currently the Transgender Program Coordinator at Equality Virginia.

While he was still an undergrad, Rae became a member of the Transgender Inclusion Shelter Project (TISP) and co-facilitator for Advocates for Richmond Youth (ARY). TISP is now under the umbrella of Diversity Richmond, where they focus on policy change and conducting agency trainings to create a safer environment for transgender persons in unstable housing.

ARY is a youth participatory action research team that aims to prevent and end youth homelessness by centering youth voices and prioritizing those with lived experience as the experts. Upon graduating in 2014, Rae began working full-time at Commonwealth Catholic Charities as an intake worker for all persons experiencing homelessness. He then transitioned to St. Joseph's Villa, where he created and implemented the state's first Youth Rapid Re-Housing Program. He acted as the intake coordinator, housing specialist, and case manager for young adults to connect them with permanent rental housing and provide life skills, job training, further education, and much more for folks to remain in stable housing.

In Rae's current role, he works to increase transgender visibility across the state and organize the Transgender Information and Empowerment Summit.