
In recognition of her groundbreaking career path in the Florida Keys, Monroe County Sheriff’s Office Capt. Lee Ann Holroyd received the 2021 Glass Ceiling Award from the Florida Federation of Business & Professional Women’s Clubs Inc. (BPW/FL), the state’s leading organization for working women.
The awards presentation was held June 18 during the 100th annual state conference at Saddlebrook Resort in Wesley Chapel. Six other members of the Upper Keys Business and Professional Women’s Club (BPW/Upper Keys) were in attendance for the awards ceremony, as were five of Holroyd’s family members. Holroyd was nominated by the BPW/Upper Keys, of which she is a member.
Most of the conference was open for virtual attendance, allowing Sheriff Rick Ramsay and at least twenty others from MSCO to virtually attend the award presentation on Zoom.
“I am very proud of Lee Ann and all of her accomplishments here at MCSO and in life,” said Ramsay. “She is one of the hardest working people that I know and is truly deserving of this recognition.”
Holroyd started working with MCSO in 1983 in a temporary staff support role. She quickly was offered a permanent spot as an assistant to the Criminal Investigations Unit.
After attending basic law enforcement academy, Holroyd was assigned to the Upper Keys as a deputy sheriff. Two years later, she was promoted to sergeant. She joined the newly created school resource officer program in the Keys and was asked to be the supervisor for the unit for the entire county.
Eventually, she spent more than 10 years commanding a federal narcotics task force focusing on the location and seizure of laundered narcotics proceeds. These investigations took her all over Europe in order to return seized assets to benefit the community she serves.
She holds many “firsts” with the sheriff’s office. She was the first female detective lieutenant and commander of special operations. Holroyd is one of the highest-ranking women in the Sheriff’s Office and on the command staff.
Today, she wears many hats: inspector general and commander of professional standards, school security and the Key West International Airport; head of Internal Affairs.
“We are so proud of our member, Lee Ann Holroyd, for setting such an example to women and girls that they can excel in any field or role, even those traditionally held by men,” said Suzi Youngberg, BPW/Upper Keys president. “She has truly shattered more than one glass ceiling, and I’m glad we were able to see her honored this way.”
BPW/FL is a statewide federation with almost 500 members in 13 local organizations. BPW/Upper Keys is the largest of the local organizations, with 85 active members.
BPW/Upper Keys went on to receive additional recognition at the state conference by winning seven awards including Best Local Organization of the Year. Margie Smith was appointed as membership chair. And, two Upper Keys members were elected to state leadership. Ilja Chapman, immediate past president and Suzi Youngberg, current president, will serve as vice president and delegate to the council of presidents, respectively, on the BPW/FL Executive committee 2021-2022.
BPW/Upper Keys supports working women professionally, politically and personally. More information is at upperkeysbpw.org or on Facebook @upperkeysbpw.



















