Leadership

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

Highly involved in the community, Dave is a member of the Board of Directors for CapeAbilities and the South Shore Economic Development Corporation. He is a former Board of Trustees member of the South Shore Hospital and former Board Member of the South Shore Chamber of Commerce, Cape Cod Young Professionals and the Community Leadership Institute.

A co-founder of the South Shore Young Professionals and recognized as a “40 Under 40” and “Rising Star 40 Under 40”, Dave sits on various advisory councils for insurance companies and is committed to helping young professionals enter and grow in the insurance industry.

Michael Robinson has been with RogersGray since 2003 and holds the title of Chairman. He 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 RogersGray, Robinson worked in finance and strategic planning for Spaulding Rehabilitation Hospital and Partners Health Care System in Boston, MA.

Recognized as a “40 Under 40” by Cape and Plymouth Business Magazine, Mike is the co-founder of the Cape Cod Young Professionals. Passionate about community involvement, he currently sits on the Board of Directors of the Cape Cod Museum of art, the Cape Cod YMCA, the Joshua A. Nickerson Society and is an Advisory Board Chair of A Baby Center. 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.

John Gaynier is Partner and Executive Vice President of RogersGray with a focus on Real Estate and Property, 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 has over a decade of experience in insurance across the US, with a specific concentration in commercial property and insures clients across the United States.

John is involved with the Boys and Girls Club of Plymouth, is a graduate of Western Michigan University and has been recognized by Insurance Business Magazine as a “Top Producer” in the United States.

Erin Schaaf, CPCU, is the Chief Operating Officer for RogersGray. Erin is responsible for overseeing all operational aspects of the agency including the service teams for personal insurance, business insurance, employee benefits and the business process team.

Erin has 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 RogersGray, she served as Assistant Vice President  Personal Lines Products, helping to set strategy for Massachusetts and Connecticut.

Erin 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).

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

Allison joined RogersGray 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 RogersGray, 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 – making her the ideal person to oversee the RG Academy.

Allison sits on the Board of Directors for Community Connections Inc., is a member of the Yarmouth Rotary Club, New England HR Association, and the Society for HR.

Lynn Mason-Small is the Chief Marketing Officer for RogersGray, responsible for the oversight of the marketing and business development team and the RogersGray Charitable Foundation.

She is a founding Board Member of the Cape Cod Young Professionals.  In addition to her years of leadership with the organization, she has served on Boards and Committees for local non-profits including the Big Brothers Big Sisters of the Cape & Islands, Community Visions, the Cape Cod Regional Technical High School, the Cape Cod Foundation, the United Way of Cape Cod and the Philanthropy Partners of Cape Cod & the Islands.

Lynn was recognized as a “40 Under 40” by Cape and Plymouth Business Magazine, is a Cape Cod native and graduate of the University of Massachusetts.

Jim Lopes is the Chief Financial Officer for RogersGray.  Over the course of his career he has held various roles in Public Accounting, Internal Audit, Planning and Analysis, Mergers & Acquisitions, Operational Analysis and Competitive Intelligence before finally joining RogersGray as Chief Financial Officer in 2012.

Prior to joining RogersGray, Jim began his insurance career at Liberty Mutual Insurance where he spent 17 years, in positions of increasing responsibility in the company’s Corporate, Commercial Market, International and Agency Market operations.

Jim, who is a Certified Public Accountant (CPA), received his BS from Bryant University and his MBA from Boston University.

Peter Cullivan is the Chief Information Officer for RogersGray, responsible for the Information Technology team at the agency.

Peter has over 25 years of professional experience in technology consulting.  Since the early 90’s, he has leveraged his leadership skills along with his strong technical background to build teams capable of designing and delivering complex technology solutions throughout the Northeast. As a technology leader, Peter led executives to make strategic technology decisions that align with their business goals.

Prior to joining RogersGray, Peter 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. Peter also 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.

Jeff Reilly is the Chief Sales Officer for RogersGray. Over the course of his career he has held various roles with companies like Gillette, Proctor and Gamble and most recently Symmons, where he was President. Jeff leads the charge on the continued development of our long-term strategy, mentorship program and growth of RG’s sales team.

Reilly holds an MBA from the Northeastern University, D’Amore-McKim School of Business and a BS from Stonehill College. He resides with his wife of 26 years and their four children in Hingham, where he is a youth athletics coach for both football and baseball.