Roger Keith Insurance

About Us

For over 140 years, Roger Keith & Sons has been a leader in providing quality personal and commercial insurance services to our community.

Roger Keith & Sons Insurance | Founders

We are a full-service Massachusetts independent agency headquartered in Brockton, MA. We also have additional branch locations in Middleboro and Marion, MA.

We offer a wide range of insurance and related financial products and services to suit the needs of both individuals and businesses. Whether you are seeking basic protection for your property, customized personal coverage for your family, or a comprehensive benefits package for your business, our staff of highly trained professionals is eager to fulfill and satisfy your needs.

Our services are delivered quickly and conveniently—whether in person, by phone, by mail, or via the Internet. We always service our customers with courtesy and consideration. Our team is committed to finding the right solution for your specific insurance needs. We take the time to listen to your concerns, understand your goals, and, most importantly, protect your future.

Our Assuralliance Membership has given us a competitive edge that affords us access to more insurance companies and more products than the average local agent. We have the clout of a national firm while still maintaining knowledgeable, friendly and efficient local service.


Donovan Dunn

President, AAI, CPIA
(508) 559-5526

  • President of Roger Keith & Sons Insurance Agency (est. 1869)
  • Over 18 Years of experience in the insurance industry and over 30 years in the Financial Services industry. Institutional Fixed Income trader with Morgan Stanley (New York) for 10 years prior to joining the agency.
  • Founded Keith, Meadows & Dunn LLC, a Life, Benefits and Financial Services agency, in 2001.
  • Northeastern University graduate (B.S.B.A. Finance, 1993 – Magna Cum Laude)
  • Registered Representative (Series 7 and 63)
  • Licensed Insurance Broker (Property; Casualty; Life; Accident; Health)
  • Accredited Advisor in Insurance (A.A.I.)
  • Current Board Member of the Signature Healthcare Foundation
  • Resides in Marion, MA with his wife Jen and three children
Sherry Meadows

Sherry Meadows

Vice President/Account Executive
(508) 559-5525

  • Vice President of Roger Keith & Sons Insurance Agency (est. 1869)
  • Commercial Lines Specialist for over 25 years
  • Passionate about helping her clients protect their Business by creating innovative insurance solutions to meet their unique needs and budget
  • Currently serves on the board of The Prom Angels – which is an organization that provides a special needs prom and Halloween party to 300 kids each year
  • Serves on a committee board at the Signature Healthcare Brockton Hospital School of Nursing
  • Past President of the Metro South Independent Insurance Agents Association
  • Served on the advisory board for Liberty Mutual Insurance
  • Served on the board of the NEGCC (New England Graphics Communications Club)

Anna Bailey

VP of Agency Operations, CIC, CRM, LIA, MLIS
(508) 559-5514

  • Vice President, Agency Operations
  • Over 29 Years of experience in the insurance industry
  • Licensed Insurance Broker (Property & Casualty)
  • Licensed Insurance Advisor (2001)
  • Certified Insurance Counselor (2006)
  • Certified Risk Manager (2012)
  • Specialties— Medical Malpractice, Hospitals, Financial Institutions
  • Placement of Coverage and Risk Management Solutions
  • Management Liability Insurance Specialist (MLIS) (2019)



Jessica Meneses

Account Executive, CPIA
(508) 559-5512


Rui Pereira

Account Executive
(508) 559-5521


Blair Breton

Account Executive, CLU, LUTCF
(508) 559-5518


Jeff Griot

Account Executive
(401) 374-8245

Commercial Lines


Elise Fiano

Account Manager – Commercial Lines, CISR
(508) 559-5515


Shanon Gallagher

Account Manager – Commercial Lines, AINS
(508) 559-5515


Donna Novo

Marketing Specialist – Commercial Lines, CISR, CPIW, AIS, AIC, AINS
(508) 559-5528

Personal Lines – Brockton Office


Diane Rowean

Account Manager – Personal Lines, CISR
(508) 583-5531


Cindy Carey

Account Manager – Personal Lines, CISR
(508) 559-5516

Personal Lines – Middleboro Office


Linda St. Don

Personal Lines Manager, LIA, CISR
(508) 559-5551


Dorine Charamba

Account Manager – Personal Lines, AAI, CPIW, CISR, CPPL, LIA
(508) 559-5552


Christopher O'Leary

Marketing Specialist – Personal Lines
(508) 559-5550

Commercial/Personal Lines – Marion Office


Lee Green

Account Manager – Commercial/Personal Lines
(508) 748-0194


Sandie McConnell

Account Manager – Commercial/Personal Lines
(508) 209-6565

Group Benefits


Katie Connolly

Group Benefits
(508) 559-5520



Sarah Kirby

(508) 559-5513


Speak to an Experienced Agent

  • Headquarters1575 Main Street
    Brockton, MA 02301

  • Middleboro Office47 Bedford Steet – Suite 2
    Middleboro, MA 02346
  • Marion Office153 Front Street
    P.O. Box 608
    Marion, MA 02738