Cutler was elected on November, 6th 2012 becoming the first Democrat to hold the seat for the 6th Plymouth District dating back to the Reconstruction era.

[1] Cutler resigned from the Massachusetts House after being appointed to a position in the administration of Governor Maura Healey.

[3] For ten years Cutler served as editor, and later publisher, of the Duxbury Clipper, a family-run newspaper first established by his grandparent in 1950.

Cutler expanded the business, launching new publications, acquiring others and bringing printing operations in-house.

[citation needed] In 2024, Cutler was named the undersecretary of Apprenticeship, Work-Based Learning, and Policy in the administration of Massachusetts governor Maura Healey.