In August 2021, Crawford resigned as the permanent City Administrator after leading the city through multiple crises, including the effects of the COVID-19 pandemic, upheaval after the death of George Floyd and the increased national awareness of injustices against BIPOC, the city's response to the climate emergency, as well as political infighting on City Council.

In February 2020, Crawford was appointed Interim City Administrator after Howard Lazarus left the city. Lazarus took a similar position as the Executive Director of Delaware County, Pennsylvania. Crawford was subsequently hired and served as the permanent City Administrator. 

In 2015, Crawford was appointed Interim City Administrator after Steve Powers left the city to take a similar position in Eugene, Oregon. In this role he also sits on the Ann Arbor Downtown Development Authority board.

In 2011, Crawford served as the Interim City Administrator after Roger Fraser left the city to take a position with the State of Michigan as Deputy State Treasurer for Government Services.

Tom Crawford served as the Chief Financial Officer for the City of Ann Arbor from 2004 through 2020.

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Timeline: Tom Crawford

October 7, 2015. Ann Arbor forms 5-member committee to start search for new city administrator. Ann Arbor News. "The council also appointed Tom Crawford, the city's chief financial officer, to serve as interim city administrator following Powers' departure. That will temporarily boost Crawford's pay to an annual rate of $159,500, which is Powers' current salary."