Roger Keith & Sons

About Us

For over 150 years, Roger Keith & Sons has been a leader in providing quality insurance services for our community.
Our practice is simple: Provide long-term value for our customers through a vast array of insurance products and expertise.
About Roger Keith & Sons

About Us

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

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Years of Service


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Meet Our Team

Donavan Dunn

Donovan Dunn

President, CIC, AAI

  • President of Roger Keith & Sons Insurance Agency (est. 1869)
  • Over 20 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.)
  • Certified Insurance Counselor (CIC)
  • Current Board Member of the Signature Healthcare Foundation
  • Current Board Member of The Brockton Hospital School of Nursing
  • Member of the Kittansett Club
  • Resides in Marion, MA with his wife Jen and three children
Sherry Meadows

Sherry Meadows

Vice President/Account Executive

  • Vice President of Roger Keith & Sons Insurance Agency (est. 1869)
  • Commercial Lines Specialist for over 30 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
  • 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

  • Vice President, Agency Operations
  • Over 30 Years of experience in the insurance industry
  • Bachelors of Science, Business Management
  • Licensed Insurance Broker (Property & Casualty)
  • Licensed Insurance Advisor (2001)
  • Certified Insurance Counselor (2006)
  • Certified Risk Manager (2012)
  • Management Liability Insurance Specialist (MLIS) (2019)
  • Specialties— Medical Malpractice, Hospitals, and Financial Institutions
  • Experienced in the Placement of Coverage, Implementation of Captives, Self-Insured and  Loss Sensitive Insurance Programs
  • Provides Risk Management Solutions
  • Serves as a Committee Member for Signature Healthcare Mission Possible Campaign
  • Resides in Franklin, MA with her husband Chuck


Jessica Bennett

Account Executive, CPIA

Rui Pereira

Account Executive

Tami Lepage

Account Executive, CISR

Blair Breton

Account Executive, CLU, LUTCF

Jeff Griot

Account Executive

Linda May

Account Executive, CIC, CISR

Peter Caldera

Account Executive

Commercial Lines – Brockton

Shannon Gallagher

Account Manager – Commercial Lines, AINS

Lee Simes

Marketing Specialist – Commercial Lines

Trevor Hart

Administrative Assistant

Personal Lines – Brockton

Diane Resendes

Account Manager – Personal Lines, CISR

Cindy Carey

Account Manager – Personal Lines, CISR

Personal Lines – Lakeville

Linda St. Don

Manager- Personal Lines, LIA, CISR

Dorine Charamba

Account Manager – Personal Lines, AAI, CPIW, CISR, CPPL, LIA

Joseph Miller

Account Manager – Personal Lines, AAI, CPI

Christopher O’Leary

Marketing Specialist – Personal Lines

Commercial Lines – Lakeville


Josalyn Caradimos

Account Manager – Commercial Lines, CISR

Victoria Pereira

Commercial Lines Assistant

Personal Lines – Marion

Lee Green

Account Manager – Personal Lines

katie stephenson

Account Manager – Personal Lines

Commercial Lines – Marion

Elise Fiano

Account Manager – Commercial Lines,  CISR Elite

Personal Lines – Weymouth

Maureen Finnerty

Account Manager – Personal Lines

Dave Auchmoody

Account Manager – Personal Lines

Commercial Lines – Weymouth

Brian Finnerty

Account Executive – Commercial Lines

Group Benefits

Katie Connolly

Group Benefits


Sarah Kirby


Catherine Johnson

Receptionist/Administrative Assistant – Brockton


Client Circle Testimonials

Been with them for a long time back to when it was Gammons Insurance. Always friendly and helps with any concerns.

Kelly H, Google Review - Lakeville

Had a very positive experience with Sandra Macedo.
She went above and beyond to assist me in taking care of my situation. She was very pleasant, full of patience, great follow ups on her phone calls and had such a great willingness to help. She made my day.

Lisa G, Google Review - Brockton

Great service. Well worth the call.

Tony Z, Google Review - Brockton

Jessica was amazing ! Great agent awesome customer services ! Offers best rates. Also gets questions or concerns taken care of in a timely manner.

Stephanie M, Google Review - Brockton

Attentive and efficient service, even well after the account is first established. Highly recommend this company to anyone who wants an agent that is on top of their insurance needs.

Jennifer D, Google Review - Brockton

Linda May, my agent at RK&S, goes above and beyond to help with questions, research and to compare rates among carriers for the best cost and coverage. She is super responsive and also very informative on what you need and also don’t need. She has years of experience in the field and really knows the ins and outs of the industry! Katie in the Marion office is very helpful too, and also very responsive.

Cathy B, Google Review - Marion

Roger Keith & Sons

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