When her father fell ill, she took over the family business and served as the Chair of the Florida Petroleum Markets and Convenience Stores Association, a trade organization.

She faced attorney Gary Gossett in the Republican primary and won the nomination of the Naples Daily News, which noted, "She has done her homework and would be an able successor to Joe Spratt" due to her experience in the private sector.

Running for re-election in 2006, Grimsley was opposed by Zane Thomas, a county planner, and the Democratic nominee.

I trust the subcommittee's judgment that this was a good leverage of tax dollars to facilitate tourism, jobs and infrastructure.

She advanced to the general election, where she faced Stacy Anderson McCland, a lawyer and the Democratic nominee.

Grimsley ran in the 2018 Florida Commissioner of Agriculture election but lost the Republican nomination to Matt Caldwell.