Call Us Today:
863.701.7411 (Lakeland)

863.676.1700 (Lake Wales)

Meet Our Team

*Headley Insurance Agency - Lakeland

  • Scott Headley

    Agency Owner / Manager
    Office: 863-701-7411 x110
    Fax: 863-701-7418
    3544 South Florida Ave
    Lakeland FL 33803
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    Scott has spent more than two decades as an innovator in the insurance industry. He works closely with both personal and commercial lines of insurance, serving as a trusted advisor to other members of the staff at Headley Insurance Agency. A certified General Lines Agent, with accreditation in life, health, and variable annuities, Scott is available to assist in the process of guiding clients toward their insurance destination.

     

    He is committed to maintaining an active presence in the communities he serves, working with local churches and the Lakeland Area Chamber of Commerce. Scott is also involved with the First Friday Group and National Rifle Association (NRA).

     

    Along with a passion for his business, Scott enjoys spending time outdoors, as well as hanging out with family and friends. 

  • Shari Headley

    Agency Owner / Accounts Payable Department
    Office: 863-617-7425
    Fax: 863-701-7418
    3544 South Florida Ave
    Lakeland FL 33803
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    Shari has served as a benchmark in the insurance industry for more than two decades. She is licensed to cater to both personal and commercial lines of insurance, and often advises fellow staff members on the appropriate plan of action. A consummate business professional, Shari oversees the accounts payable department at Headley Insurance Agency.

     

    Shari is active in promoting Lakeland Athletics, sharing her passion for organized sports for the betterment of the greater community. 

  • Wendy Cezar

    Associate Agent / Sales Manager
    Office: 863-617-7425
    Fax: 863-701-7418
    3544 South Florida Ave
    Lakeland FL 33803
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    Wendy serves as an Associate Agent at Headley Insurance Agency, specializing in commercial lines coverage. Her credentials include accreditation as a General Lines Agent, which is the most comprehensive license pertaining to property and casualty insurance. This licensure allows Wendy to tailor insurance coverage for Florida residents, families, and business owners. From homeowners insurance to various selections within our business insurance program, Wendy can write a personalized policy to meet your needs.

     

    She is a member of the Bethel Baptist Church, volunteering with the church’s youth group. In her free time, she enjoys spending time with family, camping, and playing softball. 

  • Sarah Montgomery

    Licensed Commercial Lines Specialist
    Office: 863-617-7425
    Fax: 863-701-7418
    3544 South Florida Ave
    Lakeland FL 33803
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    Sarah has been creating insurance solutions for Florida businesses since 2002. A commercial lines specialist at Headley Insurance Agency, Sarah works closely with area businesses to secure their assets. She is an Accredited Customer Service Representative (ACSR), as well as an established notary.

     

    Sarah not only advises clients, but also offers a sound game plan for the Headley Insurance Agency kickball team as the manager. Along with insurance, she’s known for creating cakes, and even runs her own cake decorating business on the side. 

  • Jonathan Cezar

    Associate Agent /Personal Lines Sales Manager
    Office: 863-617-7425
    Fax: 863-701-7417
    3544 South Florida Ave
    Lakeland FL 33803
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    Jonathan works with clients to secure a variety of personal assets, including home, auto, health, and life insurance coverage. Active in the insurance industry since 2007, Jonathan is a certified Personal Lines Agent. He is also licensed to produce life, health, and variable annuities through 2-15 accreditation. These credentials translate to a solidified insurance expertise available through Jonathan at Headley Insurance Agency.

     

    You may see Jonathan out and about in the community as a member of the Bethel Baptist Church. He is also involved with FMHA and IDPA.  Although these activities certainly keep him busy, he enjoys spending time with his grandchildren. Jonathan is a competitive shooter, and has a passion for hunting and fishing. 

  • Krista Wood

    Licensed Personal Lines Specialist
    Office: 863-617-7425
    Fax: 863-701-7417
    3544 South Florida Ave
    Lakeland FL 33803
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    Krista has been working in the insurance industry since 2009. She specializes in writing personal lines coverage for clients, securing their homes, vehicles, and other personal assets. A certified Customer Service Representative (CSR), Krista brings expertise into each policy she produces.

     

    A self-proclaimed New York Giants fan, she is an avid sports enthusiast. This passion translates into the work Krista does with a local basketball organization.  

  • Tiffany Anderson

    Licensed Personal Lines Specialist
    Office: 863-617-7425
    Fax: 863-701-7417
    3544 South Florida Ave
    Lakeland FL 33803
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    Tiffany has been working with individuals and families to secure customized insurance services for nearly two decades. A licensed Customer Service Representative (CSR), Tiffany is available to guide clients through the process of insuring their home, vehicle, and other personal assets.

     

    Away from the office, Tiffany enjoys camping and spending time outdoors. She also can’t help catching an occasional baseball game or reading a great book. 

  • Joshua Headley

    Licensed Personal Lines Specialist
    Office: 863-617-7425
    Fax: 863-701-7417
    3544 South Florida Ave
    Lakeland FL 33803
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    Josh has been active in the insurance industry since 2008. He specializes in securing personal insurance solutions for residents and families from our Lakeland office. A certified Customer Service Representative (CSR), Josh not only has a firm understanding of the risks his fellow neighbors experience, but also the ways insurance can mitigate these risks.

     

    Along with a passion for insurance, Josh is also an active outdoorsman. He is a proud supporter of Lakeland Athletics. 

Headley Insurance Agency - Lake Wales

  • Robert (Bobby) Hitchcock

    Associate Agent / Sales Manager
    Office: 863-676-1700
    Fax: 863-676-9567
    124 West Central Ave
    Lake Wales FL 33853
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    Bob has been a fixture in the insurance industry for more than a decade and currently serves clients from our Lake Wales location. He specializes in personal lines insurance, tailoring policies for individuals and their families. Whether you’re seeking coverage for your home or vehicle, Bob offers guidance toward proper protection.

     

    Away from work, Bob enjoys spending time outdoors and hunting. 

  • Kyle Pratt

    Licensed Personal Lines Specialist
    Office: 863-676-1700
    Fax: 863-676-9567
    124 West Central Ave
    Lake Wales FL 33853
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    Kyle got his start in the insurance industry in 2008, and works closely with residents in Lake Wales. Whether searching for a protective homeowners insurance policy or comprehensive auto coverage, Kyle has the knowledge and ability to secure your assets.

     

    Aside from his insurance expertise, Kyle is also a skillful poker player.