Personal guidance starts with the right person.

Jared Holloway is the Agency Manager and Senior Benefits Consultant at Holloway Benefits Group, bringing a unique combination of technical experience, insurance knowledge, and a commitment to personal service to the clients and agents he works with. Before entering the health insurance industry 12 years ago, Jared spent 32 years in Information Technology, where he built a career centered around solving complex problems, attention to detail, and helping people and organizations find practical solutions.

Today, Jared works with individuals, families, seniors, and businesses to help them better understand their coverage options and make informed decisions with confidence. His areas of focus include Medicare, Individual & Family Health Insurance, Group Benefits, and Life Insurance, but his approach is centered on something much simpler—being accessible, explaining things clearly, and building relationships with clients that extend well beyond enrollment.

As Agency Manager, Jared is equally passionate about developing the team behind Holloway Benefits Group. A major part of his goal is supporting the agency’s associates and brokers as they build their careers—providing guidance, resources, training, and mentorship to help them grow into knowledgeable, trusted, top-tier benefits professionals. He believes the strength of the agency comes from developing great agents who genuinely care about the people they serve.

Outside of work, Jared enjoys playing soccer, boating, and spending time with his wife and children. Whether on the field, on the water, or working with clients and agents, he values relationships, teamwork, and making the most of the time spent with the people around him.

Kimberly “Kim” Walters is a licensed Virginia insurance agent and Senior Benefits Consultant with Holloway Benefits Group. A lifelong Hampton Roads resident, Kim helps individuals and families navigate health insurance, Medicare, dental, vision, and life insurance with an emphasis on clear guidance, personal service, and finding coverage that fits each client's needs.

Before entering the insurance industry, Kim built a diverse professional career that combined technical expertise, business management, and healthcare advocacy. She began her career with Northrop Grumman, where she worked in aircraft carrier design. She later spent more than 20 years with a pharmacy management company, including managing a patient assistance program that helped uninsured and underinsured cancer patients access needed support.

That experience gave Kim firsthand insight into the challenges individuals and families can face when navigating healthcare and coverage. Her passion for helping others ultimately led her to become an insurance agent, where she continues that work by helping clients better understand their options and make informed decisions about their health and life insurance needs.

Kim holds a degree in Drafting & Design, a degree in Business Management, and an MBA in Accounting, bringing a unique combination of technical, business, financial, and healthcare experience to her work with clients.

A strong believer in hard work, integrity, and outstanding client service, Kim values building relationships with her clients and being a resource they can turn to as their insurance needs change.

Outside of work, Kim enjoys traveling and spending time with family and friends. She lives in Poquoson, Virginia, with her two children.

Jessica Felder is a licensed health insurance broker specializing in individual health insurance and supplemental Medicare coverage. With more than a decade of experience in administration, human resources, financial management, and employee benefits, she brings both professional expertise and a personal approach to helping individuals and families find coverage that fits their needs.

Before entering the insurance industry, Jessica held leadership and administrative roles with The Williamsburg Winery and David A. Nice Builders, working in budgeting, financial analysis, employee benefits, and human resources. She earned her bachelor's degree in Political Science from Christopher Newport University, with a focus on Government Administration and Policy Analysis.

Jessica also has a personal connection to the military community through her father, a retired Army pilot. She lives in Williamsburg with her husband and their two children and enjoys spending time with her family at Colonial Williamsburg and Busch Gardens.

Arianna Giles is a Benefits Consultant with Holloway Benefits Group who brings a thoughtful, personal approach to working with individuals and families. She enjoys getting to know her clients, understanding what matters most to them, and making what can sometimes feel like a complicated process much easier to navigate. Her goal is to provide clear, patient guidance so clients feel comfortable asking questions and confident in the decisions they make.

With a professional background in administration and human resources, Arianna brings strong organizational skills, attention to detail, and a genuine commitment to customer service to her work. She takes the time to understand each client’s individual situation and believes guidance should be personal, straightforward, and never rushed or overwhelming.

Arianna enjoys helping individuals and families feel confident as they navigate their health coverage options. She assists clients with Virginia’s Insurance Marketplace, providing guidance throughout the application and enrollment process and taking the time to explain their options in a clear, straightforward way.

Arianna lives in Newport News, Virginia, with her husband and their German Shepherd. Outside of work, she enjoys inshore and offshore fishing, snowboarding, spending time with family, and getting outdoors whenever she can.