He also served as a teaching assistant to Ed Miliband, now a British MP and formerly the leader of the Labour Party, in a course comparing US and northern European social policy.

[3] In July 2004, Ashe successfully sought a seat on the Burlington City Council in a special election to replace Carina Driscoll.

In the Fall of 2006, Ashe became a Project Manager at Cathedral Square, a non-profit developer of affordable housing for seniors and people with disabilities.

[5] While seeking the Democratic nomination for Mayor on November 13, 2011, Ashe tied Miro Weinberger in the party caucus, with each receiving 540 votes after three rounds.

[10][11] In April 2021, Doug Hoffer, the Vermont State Auditor, announced that he had hired Ashe as his deputy.

[12] Ashe succeeded Andrew Stein, who left the deputy auditor's post for a position with the Vermont Department of Taxes.