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Rogers & Gray was named the “Best Agency to Work For” in the Nation in 2015 by Insurance Journal Magazine, the industry’s top trade publication.

People, culture, strong leadership, respect, profitability, growth and community involvement are all hallmarks of the Rogers & Gray employee experience.  Our working environment is outstanding, our corporate culture is strong, our benefits package is highly competitive and our future is bright.  Visit our Careers page to learn more about working at Rogers & Gray.

Michael C. Robinson
Chairman of the Board | Partner

Michael Robinson holds a Bachelor’s degree in Health Care Administration from Ithaca College in New York and a Masters in Business Administration from the University of Massachusetts.

Prior to joining Rogers & Gray Insurance, Mr. Robinson worked in finance and strategic planning for Spaulding Rehabilitation Hospital and Partners Health Care System in Boston, MA.

Michael has been employed by Rogers & Gray Insurance Agency since 2003, is one of 3 principals, and currently holds the position of Chairman of the Board.

Michael is current member of the Board of Directors of the Cape Cod YMCA and is a co-founder of the Cape Cod Young Professionals. He is a past board member of the Hyannis Chamber of Commerce, Rotary Club of Harwich-Dennis, and has served on various committees at the Rehab Hospital Cape & Islands, Cape Cod Playhouse, & Cape Cod Foundation.

Michael resides in Dennis, MA with his wife and daughters.


David T. Robinson
President & CEO | Partner

A graduate of Tabor Academy and the University of Colorado at Boulder, David Robinson joined the agency in 2004, is one of 3 agency principals and holds the position of President & CEO.

David sits on various advisory councils for insurance companies and is a Trustee on the South Shore Hospital Board of Trustees.

He is the co-founder of the South Shore Young Professionals and current Board Member of the South Shore Chamber of Commerce and CapeAbilities. His past community involvements include the Cape Cod Young Professionals  and the Community Leadership Institute.

David currently lives in Norwell with his wife and their children.


Bizak_RobertRobert Bizak
Executive Vice President | Partner

Robert Bizak joined Rogers & Gray in 2001 and holds the position of Executive Vice President. Mr. Bizak has over 25 years of insurance experience, both on the carrier and agency sides of the business and currently oversees the Commercial Insurance Department for the agency.

A graduate of Suffolk University, Robert holds a Massachusetts Insurance Brokers License and has served on many insurance carrier advisory boards including as Regional Chairman for the Peerless, CNA and National Grange advisory councils and as National Chairman of the Main Street America Council. Additionally, Bob served on an industry board for the Utility Contractors Association of Massachusetts.

He is currently serving as the President of the Plymouth Agents Association, member of the South Shore Chamber of Commerce Economic Development Committee and Vice Chairman of the YMCA – Mill Pond Board of Directors.

Bob resides in Hanover, with his wife and daughter.


John Gaynier
Executive Vice President | Partner

John Gaynier joined Rogers & Gray in 2012 and holds the position of Executive Vice President. John has more than a decade of insurance across the U.S., with a specific concentration in commercial property, focusing primarily on real estate, hospitality, transportation and construction insurance needs.

He holds an AAI designation – Accredited Advisor of Insurance, and was a member of the MarshBerry MAPLYT program, a mentorship and apprenticeship program established for emerging young leaders in the industry by the nation’s top industry consulting firm.

John is a graduate of Western Michigan University and lives in Sandwich with his wife and son.


Frommeyer_Allison (2)Allison McEachern
Chief People Officer, Senior Vice President

Allison McEachern is responsible for Rogers & Gray’s most trusted asset – its people. As Chief People Officer, Allison oversees the agency’s hiring and training functions.

Allison joined Rogers & Gray in 2011 as an Account Executive in our Employee Benefits division, and most recently held the role of Director of Employee Benefits. Prior to joining Rogers & Gray, Allison’s past Human Resources experience included positions at Frito Lay, Inn Seasons Resorts and The Black Dog.

Allison holds a Bachelors Degree from Stonehill College and is Massachusetts licensed as a Life & Health Producer. Allison is also MA licensed as a Middle School and High School teacher and prior to beginning her HR career she taught Social Studies on and off Cape Cod.

Allison currently lives in South Yarmouth with her husband and their children.


Mason-Small, LynnLynn Mason-Small
Chief Marketing Officer, Senior Vice President

Lynn Mason-Small is the Chief Marketing Officer for Rogers & Gray Insurance Agency, where she oversees Business Development, Corporate Communications, the Rogers & Gray Charitable Foundation and the Corporate Giving policies for the Agency.

Mason-Small is a founding Board Member of the Cape Cod Young Professionals. She has also served on boards and committees for local non-profits including Philanthropy Day on Cape Cod, the Big Brothers Big Sisters of the Cape & Islands, Community Visions, the Cape Cod Regional Technical High School, the United Way and the Cape Cod Foundation.

Prior to joining Rogers & Gray, Lynn held previous positions in marketing, strategic program development and event planning.  Lynn is a graduate of the University of Massachusetts and lives with her husband, Nathan Small and 2 sons in South Yarmouth.


Jim Lopes
Chief Financial Officer, Senior Vice President

Jim Lopes received his Bachelors Degree from Bryant University in Rhode Island and Masters Degree from Boston University and is the Chief Financial Officer at Rogers & Gray Insurance. He joined Rogers & Gray in 2012 after many years with a national insurance carrier.

He is a licensed CPA and has over 15 years of industry experience including in; Mergers & Acquisitions, Financial Reporting, planning and analysis, Competitive Intelligence and Operational Analysis.

Jim resides in Mansfield with his wife and sons and enjoys being involved in his children’s sporting activities.



Peter Cullivan
Chief Information Officer, Senior Vice President

Peter Cullivan is the Chief Information Officer for Rogers & Gray Insurance Agency. As CIO, Cullivan oversees the technological capabilities and advancements of the agency as they relate to client experience, internal efficiencies and support services.

Prior to joining Rogers & Gray, Cullivan worked for All Covered, a division of Konica Minolta. He joined All Covered in 2001 as lead engineer for the technology team and transitioned into several roles including Vice President of Technology and Service, Director of Service Delivery, Managing Director and most recently as Strategic Account Management. Previously, Cullivan held positions at Dimension Data, where he was responsible for the engineering team and its successful design and integration of enterprise class networks, and Brown Brothers Harriman, where he was a lead engineer.

Peter lives in Weymouth, MA with his wife and their four children.


Erin Schaaf
Chief Operating Officer, Senior Vice President

Erin Schaaf is the Chief Operating Officer for Rogers & Gray Insurance Agency. As COO, Schaaf oversees the business operations of the agency and works with senior management and the divisional directors to design and implement business strategies, plans and procedures.

Schaaf joined Rogers & Gray with nearly three decades of experience in the insurance industry. Most recently, she served at Arbella Mutual, where she held various leadership roles in personal lines products, underwriting and fraud detection. Prior to joining Rogers & Gray, she served as Assistant Vice President Personal Lines Products, helping to set strategy for Massachusetts and Connecticut.

Schaaf received a BS in Mathematics at Bridgewater State University and a Masters of Science in Insurance Management from Boston University. She also holds a CPCU Designation (Chartered Property Casualty Underwriter). She has volunteered with local Father Bill’s & MainSpring homeless shelters for many years.