Gretchen Guess served on the Anchorage School Board from 2011 to 2013 and was president of the school board. Guess was a consultant and business analyst. From 2001 to 2003, Guess served in the Alaska House of Representatives and was a Democrat. She then served in the Alaska State Senate from 2003 to 2007. In 2013, Guess resigned from the school to take a job at St. Vincent’s HealthCare in Jacksonville, Florida.