Senior Finance Director Raymond O. Bailey

Born: Welch, WV

Education: Bachelor of Business Administration, Stetson University; Masters of Accountancy, Stetson University, Certified Public Accountant, Certified Insurance Counselor, Certified Risk Manager, Chartered Global Management Accountant

Lake County Sheriff's Office
Senior Finance Director: 03/2017-present

Sidecar HR
Senior VP of Finance: 2016-2017

Angela Adams Consulting
Financial Analyst: 2015-2016

Brown and Brown, Inc.
Operations Manager: 1996-2015

United States Army
Infantry- Honorable Discharge: 1988-1991

Senior Finance Director Raymond O. Bailey 

was born in Welch, WV. He is a graduate of Flagler Palm Coast High School. Mr. Bailey proudly served in the United States Army 10th Mountain Division. Upon completion of his enlistment with the United States Army, he went on to receive his Bachelor of Business Administration and Masters of Accountancy from Stetson University. Mr. Bailey has spent majority of his career in the Insurance and Payroll Industries before joining the Sheriffs Office.

Mr. Bailey has served on the board of the Boys and Girls Clubs, as well as Treasurer of the Leesburg Rotary. He has three sons; Logan, Drew, and Elijah. Currently resides in Leesburg, FL.