Leadership Bios


Donald T. 'Scotty' Scott, CPCU


Scotty opened Sycamore Insurance Associates in 2011. He has been involved in the insurance agency business since graduating from Indiana University in 1986 with a bachelor's degree in Business Accounting. He holds the Chartered Property Casualty Underwriter designation, the highest designation in the industry. Prior to Sycamore Insurance Associates he worked for Indiana's largest retail insurance agency and held positions such as Regional President, Chief Operating Officer and Account Executive. Scotty is a lifelong resident of Terre Haute and is currently serving as Vice Chairman of the Union Health System board.  He also serves on the boards of Union Health Foundation, Vigo County Education Foundation, VNA/Hospice of the Wabash Valley, and is past President and member of the Downtown Terre Haute Rotary Club.  He and his wife Anna have six children and they enjoy keeping up with all the kid's activities. 

Jason B. Lester, CIC

Vice President of Sales

Jason has over 15 years experience in group benefit plans as well as property and casualty insruance. He has been directly involved in managing multi-state employers with 1000-plus employees in a broad spectrum of industries including energy, healthcare, auto dealers, manufacturing, and motorsports. He is a member of the State and National Associations of Health Underwriters. He holds llife and health as well as property and casualty licenses in multiple states across the nation and is a designated Certified Insurance Counselor (CIC). He holds a bachelor’s degree in marketing from Indiana University’s Kelley School of Business.

Chad Cates

Vice President

Chad is Sycamore Insurance Associates’ vice president working with Commercial Property & Casualty and Group Benefit accounts. He specializes primarily in the healthcare, social service, manufacturing and agricultural industries. Chad holds licenses in Property & Casualty and Life & Health insurance in Indiana and Illinois. He works directly with customers to develop appropriate risk management strategies that are tailored to their specific needs. Chad has assisted employers in setting up partially and fully self-insured workers’ compensation programs and takes a proactive approach when working with his customers. A Terre Haute native, he graduated from Indiana State University with majors in Insurance & Risk Management and Business Administration.



999 Ohio Street
Terre Haute, IN 47807

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