Hired as Rye’s Assistant City Manager in 2005, Mr. Pickup was passed over by the Otis Administration for the City Manager position in 2009 following the termination of Paul Shew. Mr. Pickup continued in his Assistant role under Interim City Manager Frank Culross who was brought out of retirement to run the city.

In 2009, Doug French, the Republican candidate for Mayor, asserted his desire to appoint Mr. Pickup as Rye City Manager, something that became a reality in July of the following year after French’s successful election.

Over the next three years, Mr. Pickup developed a close yet politically divisive alliance with Mayor Doug French and his Deputy Mayor, Peter Jovanovich. Together, the trio developed a plan that enabled Hen Island residents to jerry-rig unpermitted sewage disposal systems without inspection or approval from any municipal authority.

Throughout his tenure, Mr. Pickup became commonly known for his defense of the Kuder Island Colony Corporation, which included his besiege of Ray Tartaglione at City Council Meetings.

In April of 2014, Mr. Pickup signed a separation agreement with the City of Rye, resigning from his post.