Who We Are

Thirty-five years ago, William J. Cleary III and his father, William J. Cleary Jr., started an insurance agency built on a simple premise: the best policy is the one that actually protects you when you need it. Cleary Insurance is a Boston-based independent insurance brokerage.

Today, Cleary is a mid-sized team of licensed insurance professionals serving businesses and individuals throughout Massachusetts and New England.

Our History

Cleary Insurance was founded in 1991, opening its first office on Boston’s Portland Street with a small team and a clear focus: hire the most experienced professionals in the industry and invest in their ongoing development. That commitment to expertise over volume has defined the agency ever since.

Over the past three decades, Cleary has grown from one office to three — adding locations in Quincy and Peabody through a combination of organic growth and the 2017 acquisition of Wedgewood and Crane Insurance — and from a handful of staff to 36 employees, including a dedicated Claims department.

Today, Cleary represents more than 50 carriers across commercial property & casualty, personal lines, life, and group benefits, including medical, dental, and related coverages. Most agencies specialize in only property/casualty or group benefits; Cleary does both, which means clients get a genuinely integrated view of their risk and coverage needs under one roof.

What Makes Us Different

Insurance agents who work for a single company can only offer that company’s products. Cleary is independent, which means we represent more than 50 carefully selected carriers. When you need coverage, we compare the market and recommend the best option to fit your situation.

What We Offer

Cleary provides coverage in four areas:

• Commercial Insurance — general liability, workers’ compensation, commercial auto, professional liability, cyber, and more for Massachusetts and New England businesses of all sizes
• Personal Insurance — homeowners, auto, renters, condo, umbrella, valuable articles, boat, and motorcycle coverage for Massachusetts and New England residents
• Life Insurance — term, whole life, disability, long-term care, and key employee coverage
• Group Benefits — health, dental, vision, disability, and voluntary benefits for Massachusetts employers, managed by a single dedicated contact

Our Approach

At Cleary, we believe life is worth the risk. Our role is to make sure you’re ready for it. Backed by a network of trusted carriers, we take the time to understand your business and your unique situation—building customized insurance solutions that protect what you’ve built and support what’s next.