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Ryan Gillispie - Executive Vice President

As Executive Vice President at Highland Risk Services, Ryan is responsible for wholesale brokering of P&C Insurance for long-term care facilities and allied health providers, as well as participating in the general management of the company. Ryan possesses over 10 years of insurance industry experience with a specific emphasis on various specialty liability lines, including the healthcare sector. This experience, along with previous roles that include being a retail broker and manager of an Underwriting/Wholesale division for a specialty MGA, have given him a great understanding of the needs and expectations of retail brokers and underwriters alike. Ryan uses his communication skills and his expertise in sales and marketing to better understand the needs of clients and deliver information in a clear and concise manner.

Ryan holds a Property & Casualty license and a Surplus Lines Broker license. He earned a Bachelor of Arts in Communications, from California State University-San Marcos where his scholastic efforts landed him on the Dean’s list.

Outside of work, Ryan enjoys spending quality time with his wife and three children, and staying in touch with family and friends. Ryan, an avid baseball fan, had a short Minor League baseball career with the Pittsburgh Pirates, and is also interested in various sports, music and outdoor activities.

Office: (847) 832-9099


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