Personalized. Individual. Employee. Benefits.

Gwendolyn Bailey, known as Gwen, began her career in insurance in 2015 as a benefits advisor with Aflac, the world’s largest supplemental insurance company. In response to her clients’ growing needs for comprehensive business solutions and employee benefits, she established Bailey Insurance Group (BIG) in 2021.

Based in Wake Forest, BIG is committed to delivering ethical, integrity-driven insurance solutions tailored specifically for small businesses and individuals.

Gwen’s diverse work background enriches her approach to client service. With experience in computer sales, marketing, manufacturing procurement, and legal services, she skillfully offers her clients “BIG Benefits Every Stage of Life.”

Services offered by BIG include supplemental insurance, HR/payroll solutions, virtual care/telemedicine, life insurance, dental & vision and Tax & FICA savings programs.

A proud North Carolina native, Gwen grew up in Jacksonville and later moved to Raleigh, where she earned an associate’s degree in general studies from Peace College, followed by a bachelor’s degree in communication from North Carolina State University.

Gwen is passionate about community involvement, serving as a Rolesville Chamber of Commerce ambassador for eight years and currently as a member of the Board of Directors. She became a member of the Wake Forest Area Chamber of Commerce in 2015. Gwen is an active member of the Senior Information & Networking Group of Wake Forest, and Women in Networking where she served as vice president and referrals coordinator. Additionally, she dedicated two years to serving as a Wake County Guardian ad Litem.

Gwen and her husband, Mike, have been married since 2004. In 2021, they adopted their daughter Sabrina at age 13. As a family, they cherish their pets—Lulu the German Shepherd and Ginger the calico cat—plus their time together camping, boating, and all things outdoors.