Toby Arkwell

At Communitively, as in past roles, I focus on organizational governance, helping events run smoothly, and day-of volunteer support.

Toby Arkwell has dedicated more than 30 years to helping individuals, families, and businesses find health insurance and employee benefit solutions that meet their needs and budgets. Beginning his career with the family business, RW Insurance, and later founding RW Health Benefits, Toby has built a reputation as a trusted advisor known for providing honest guidance, personalized service, and practical solutions. As an independent insurance agent licensed in New Hampshire and Maine, he works closely with clients to help them navigate health insurance, Medicare plans, and employee benefit programs with confidence and clarity.

Throughout his career, Toby has been committed to helping people make informed decisions during some of life's most important moments. His approach is built on trust, accessibility, and a genuine desire to serve as a reliable resource for the individuals, families, and businesses he supports. He believes that strong relationships and straightforward advice are the foundation of exceptional service.

Beyond his professional career, Toby has been a lifelong volunteer and community leader throughout the Greater Dover area. He has served on the boards of numerous nonprofit organizations, including the Greater Dover Chamber of Commerce, Dover Children's Home, and the Seacoast Endowment for Education in Dover (SEED). During his time with the Chamber, he served as Board Chair and helped guide the organization through important initiatives supporting local businesses and the broader community. In recognition of his many years of volunteer service, Toby was honored as the Greater Dover Chamber of Commerce Volunteer of the Year in 2017.

Known for both his leadership and his willingness to do the work behind the scenes, Toby has contributed to countless community projects, events, and committees over the years. Whether helping oversee governance, supporting organizational strategy, coordinating events, or tackling logistical challenges that others might avoid, he brings a practical, hands-on approach to every role. His commitment to service is perhaps best illustrated by his willingness to take on responsibilities such as managing waste and cleanup operations for Apple Harvest Day, one of New Hampshire's largest festivals, ensuring the event could continue to be a positive experience for tens of thousands of visitors.

As a board member of Communitively, Toby brings decades of experience in business, nonprofit leadership, governance, and community engagement. He is passionate about helping organizations operate effectively, supporting local businesses, and creating opportunities that strengthen the connections that make Dover such a special place to live, work, and visit.