Rob MacCallum

A Decade of Expertise, Rooted in Service

Rob MacCallum is the principal owner of MacCallum Group and brings over ten years of experience in the insurance industry—along with a strong belief that personalized service still matters.

After earning his degree in Science and Business Administration from Nichols College, Rob began his career in sports management, where he led teams and honed his skills in leadership and client service. But it wasn’t long before he realized he wanted to make a different kind of impact—helping people protect what matters most.

He transitioned into insurance and began building his foundation at Liberty Mutual, completing their nationally recognized training program focused on personal insurance lines. Rob traveled across the country to learn directly from Liberty’s top professionals and developed a keen eye for matching clients with policies that truly fit.

His path then led him to the commercial side of insurance with Travelers, where he deepened his understanding of business policies and risk protection. Over time, Rob became a trusted resource for both individuals and business owners, combining deep product knowledge with real-world insight.

Why MacCallum Group?

After working at larger firms, Rob saw a clear gap in the industry: great products, but impersonal service. That realization drove him to seek out a smaller agency with a stronger local connection. He joined a South Shore-based private firm, quickly moving into leadership—first as a manager, then partner, and eventually as owner.

Today, Rob leads MacCallum Group with a clear mission: deliver high-quality insurance solutions, backed by a real relationship. He believes coverage should be clear, policies should fit your life, and service should always feel personal—whether you’re insuring your home, your business, or both.