Matthew Crum - President
Leadership team

Matt Crum is the President of Frank Winston Crum Insurance and sits on the Board of Directors. He is responsible for managing the operations of the insurance company and works closely with the PEO’s management team on workers’ compensation and other company initiatives. Matt is also the Co-President of FrankCrum, alongside Haley Crum. The two are jointly responsible for operations, product, customer service, technology, marketing and compliance. Matt grew up in the Tampa Bay area, where he earned an M.B.A. with a concentration in Finance from the University of Tampa. He is also a graduate of Trinity College in Hartford, CT, with a Bachelor’s degree in Economics and Religion. Matthew serves on several boards in the Tampa Bay area, including the YMCA of the Suncoast, the Clearwater Downtown Partnership, and the Clearwater Regional Chamber of Commerce. He was a finalist for the Tampa Bay Business Journals’ Up & Comers award in 2013. He is a licensed insurance agent (20-20 and 20-15 licenses) and is a Certified Insurance Counselor.

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Jim Carr – Chief Financial Officer
Leadership team

Jim Carr serves as Chief Financial Officer and Treasurer of Frank Winston Crum Insurance, as well as on the Board of Directors. Jim graduated from Ursinus College with a Bachelor’s degree in Business Administration with a concentration in accountancy. He began his insurance career in 1994 at the Florida Residential Property & Casualty Joint Underwriting Association. Five years later, he obtained the designation of Associate in Insurance Accounting and Finance from the Insurance Institute of America, and became a Certified Public Accountant. He has been with Frank Winston Crum Insurance since its inception.

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Herb Curlee – Director of Casualty Programs
Leadership team

Herb Curlee serves as our Director of Casualty Programs. Herb has worked for over 40 years in the property-casualty industry after graduating from the University of Virginia. In the 1990’s, he served as founder and chief software architect of Evolution Technology, a national rating vendor that specializes in auto and GL rating for insurers throughout the U.S. Before joining Frank Winston Crum Insurance in 2013, Herb served for a decade as the Director of Commercial Products and Director of Marketing for the Cypress Insurance Group in Jacksonville, Florida.

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Paul DiFrancesco – Sr. VP of Business Development
Leadership team

Paul DiFrancesco is the Sr. VP of Business Development for Frank Winston Crum Insurance, where he manages and coordinates the sales activities of the FWCI Business Development team. A senior executive with over 40 years of insurance industry experience, Paul brings a highly innovative, ethical, and results-oriented approach to strategic and tactical planning. A graduate of Fordham University in New York, ​and an MBA at University of Hartford, Paul spent 15 years at Travelers Insurance, before stints at ​ACE, White Mountains, PMSI, Direct General and others over the following 20+ years. Immediately prior to joining FrankCrum, Paul served five years as the Chief Operating Officer for United Insurance Holding Corp. in St. Petersburg, where he directed all Product Management, Underwriting, Operations, Actuarial and Data Analytics for the $1.3B Personal and Commercial property writer.

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Steve Gober – Vice President of Underwriting
Leadership team

Steve Gober oversees all of the underwriting activities for FrankCrum’s workers’ compensation insurance programs. This includes PEO underwriting, guaranteed cost underwriting, as well as loss sensitive or program business. He started his insurance career with Texas Employers Insurance Association as a commercial casualty underwriter. He was there for two years before joining The Hartford in the national accounts department where he stayed for 18 years. Most recently, Steve was Vice President and Director of Underwriting for Imperial Casualty and Indemnity Insurance Company. While at Imperial, he developed the startup company to over $100 million in manual premium.

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George Schwab - Vice President of Operations
Leadership team

George Schwab is a dedicated member of the senior leadership team, serving as the Vice President of Operations. With more than 20 years of diverse experience within the insurance sector, he works to optimize the company’s operating capabilities and employs strategies to maximize customer satisfaction to support business expansion. Through iterative transformation practices and with a commitment to risk management, he leads customer-centric initiatives. George most recently has held key roles at innovative, technology-focused organizations such as Roost, Capgemini, Majesco, and the CGI Group and has also managed insurance operations for several large and regional carriers. He received an M.B.A. from Southern New Hampshire University and a B.A. in Political Science from Colorado State University.

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Terra Wilhelm - Vice President of Litigation and Director of General Liability
Leadership team

Terra graduated from the University of Wisconsin Milwaukee with a Bachelor’s degree, Summa Cum Laude, in Psychology and attained her Juris Doctor degree from Stetson University College of Law in Florida in 2003. Terra’s career has focused on defending corporations, individuals, insurance companies and their insureds as a litigator and partner in private practice. She has a broad range of Trial practice and is admitted to practice before all Florida State Courts and the United States District for the Middle Districts of Florida. She has handled numerous complex claims, including wrongful death, products liability, trucking, automobile, construction defect, premises liability and insurance coverage cases. Terra has been named and recognized by Super Lawyers and Florida Legal Elite. In her position at FWCI, she is responsible for management of the general liability litigation and claims administration portfolios to include oversight of both the Third Party Administrator (TPA) and outside counsel, resolution of disputes, coverage and claim analysis, and risk management, along with a broad variety of legal services.

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