Ross, a trans woman, has said she was perceived as feminine from a young age. In 1998, at the age of 17, she came out as gay to her mother, an evangelical Christian; "She told me I should commit suicide or she would, because she couldn’t have someone like me as her child." Ross considered ending her own life and overdosed on medication, but survived.
Ross moved to Hollywood, Florida and worked as a model and escort until 2003. She started a web development and graphic design Business, and began taking acting classes. She later moved to Chicago to become the employment coordinator for the Trans Life Center.
Ross launched TransTech Social Enterprises in Chicago in 2014. The nonprofit creative design firm trains and contracts transgender and other workers. Melissa Harris-Perry brought more attention to the firm in 2015, choosing Ross as her show's first "Foot Soldier" of the year. Ross was a featured speaker at the 2015 White House LGBTQ Tech and Innovation Summit.
In 2016, Ross began acting in Her Story, a web series about trans women in Los Angeles. The series was nominated for an Emmy Award for Outstanding Short Form Comedy or Drama. Ross also made a guest appearance that year on the TV series Transparent.
In June 2017, Ross began providing voice work for the Amazon Video animated series Danger & Eggs.
