Click here to access our COVID-19 resource center.

Join Our Team

Check out why RG is the best match for you!

Voted the “Best Agency to Work For” in the United States…
“Best Places to Work” by Boston Business Journal…
Top Places to Work” by the Boston Globe.

Find out why…

Matchmaking is our specialty.

We like to pair up wonderful people with our wonderful team. So swipe right on the button below to see what openings RogersGray has that might be attractive to you.

Grow your skills. Hone your craft.

Some of our team have come to RogersGray with no experience and some have come with a career full of experience. The common denominator is their constant thirst for knowledge, to constantly learn and develop.

Supporting You & Your Family...

We take our benefits seriously because we care about our team and their families. From vacation homes to health insurance to maternity & paternity leave and everything in between, RogersGray’s benefits package is comprehensive and meant to protect you and your family and let you enjoy time off with them.

Enjoy helping others? This may be a perfect role for you! Within the Client Manager role employees help existing customers with their insurance needs by problem solving, listening, researching and overall caring for their clients. “I love how my job grants me the ability to help people and protect them from the unexpected things that come their way.”- Tory Furtado, Client Manager, Personal Insurance

Love getting that sale while helping others and being active in the community? Then a sales role with RG may be a great fit for you. The RG sales teams take pride in offering consultative sales approaches to prospective clients while working actively within the community. “I feel like the level of effort I put in is appropriately rewarded and recognized by everyone at RG. Its great that my input and opinions are valued by my manager and the owners. This pushes me to help my clients more and more everyday.” Adam Trivilino, Consultant, Small Business

The service and sales teams need the support of the agencies operations teams to get the work done. Without risk placement, business development, human resources, finance and the processing department this ship would not move so smoothly. Come join this awesome team. Working at RogersGray has been just awesome. Every day I am challenged and grow professionally – plus I’ve made wonderful friends!” – Jessica Alfieri, Business Development Specialist 

What Our People Say!

When I come to work I feel like I’m not at work. Its such a welcoming environment with a focus on development, career growth and achieving your goals along with the companies. Overall a great place to work!


Client Manager

RogersGray’s building blocks of training has developed me to be an expert in my field, not just another salesman. This expertise has instilled a level of confidence that allows my clients to trust me with protecting their assets.


Insurance Consultant

Communication is excellent.  The owners are very accessible and go out of their way to over communicate.   The culture is strong and leadership believes in the values of the organization and demonstrates it every day.



Our People

These are our real people. We’re not going to lie, we had to use a little stock photography through our website, but most of the smiling faces are members of our own team. Client Managers, IT, Sales, Processing Department, Marketing, Risk Placement, Finance…you name it. The smiles are genuine too.

Contact Us

434 Route 134
South Dennis, MA 02660

Phone: 508-619-4545

Fax: 877-816-2156

24 Hour Emergency Claims Center:



Get helpful tips, and insurance insights delivered right to your inbox!