After graduating from university in 2009, Freedman-Gurspan joined the Massachusetts Transgender Political Coalition, where she worked on legislative and policy issues. In January 2010, she was hired by Mayor Joseph A. Curtatone of Somerville, Massachusetts to serve as the city's LGBT liaison. Through her work with the MTPC and as Somerville LGBT Liaison she met then-Massachusetts State Representative Carl Sciortino, a MedfordDemocrat. At the time he was one of the lead sponsors on a bill in the state legislature that would expand state civil rights protections to transgender residents. In July 2011, Freedman-Gurspan join Sciortino's office as a legislative aide, becoming the first openly transgender legislative staffer in the Massachusetts State House. She played an instrumental role in helping Sciortino pass the transgender civil rights bill in November 2011, which was signed into law by then-Governor Deval Patrick in January 2012. Freedman-Gurspan worked as Sciortino's legislative director until he retired from the MassachusettsHouse of Representatives in the spring of 2014. In July 2014, Freedman-Gurspan was hired as policy advisor at the National Center for Transgender Equality and moved to Washington, DC. There her work focused on issues facing transgender people of color and those living in poverty. Her work included criminal justice and incarceration reform, immigration detention conditions, housing and homeless shelter policies, and sustainable economic development opportunities for transgender people in the United States. On August 18, 2015, Freedman-Gurspan was hired by President Barack Obama as Outreach and Recruitment Director in the Presidential Personnel Office at the White House, becoming the first openly transgender person to work as a White House staffer. He subsequently appointed her as the White House’s primary LGBT liaison in 2016, making her the first openly transgender person in the role. She served in this role until January 6, 2017. On January 17, 2017, President Obama appointed her to a 5-year term as a member of the United States Holocaust Memorial Council, the Board of Trustees of the United States Holocaust Museum in Washington, DC. On April 3, 2017, Freedman-Gurspan rejoined the National Center for Transgender Equality as its new director of external relations. In this role she led and enhanced NCTE's organizing and public education efforts, and supported the organization’s policy and communications programs. In May 2019, Freedman-Gurspan left NCTE to become Deputy Campaign Director for the All on the Line Campaign, a project with a mission to end gerrymandering.