[1] He attended Montgomery County Public Schools and lives in Takoma Park, Maryland.
[2][3] Jentleson received a BA in American History from Columbia University in 2003.
[4][5][6] Jentleson began his career as a policy researcher and speechwriter for the John Kerry 2004 presidential campaign.
[7] He then served as Manager of Congressional Affairs at the Center for American Progress, speechwriter for the 2008 presidential campaign of John Edwards.
[8] Jentleson served as communications director and, later, deputy chief of staff for United States Senator Harry Reid from 2010 to 2016.