Who We Are

Why Bailey Howes Insurance?

We Care About Protecting Your Whole Life

For more than thirty years, Bailey Howes Insurance Group has provided tailored insurance solutions and trusted risk management guidance to individuals and families across Concord, Massachusetts, and beyond.

Our holistic, consultative approach begins with understanding each client’s unique circumstances, from family and career to community involvement, financial goals, and future aspirations. By seeing the whole picture, we are able to design comprehensive strategies that help our clients confidently manage risk and safeguard what matters most.

Meet Your Leadership Team

We are dedicated to developing insurance and risk management solutions that protect every facet of your life.

Greg Howes

Founder and CEO

Greg Howes began his insurance career as a property claim adjuster at Great American Insurance Company, but his entrepreneurial spirit soon led him in a new direction. In 1993, Greg and his father acquired a small agency in Acton, Massachusetts, and launched The Howes Insurance Group. By the late 1990s, Greg purchased his father’s interest and relocated the agency to Concord, Massachusetts, where it continues to grow and thrive today.

Concord is more than just a business address—it’s home. Greg raised his family here, built enduring relationships, and devoted over 15 years to public service in town government. That deep local connection continues to shape our reputation for integrity and a truly client-focused approach.

Over the years, the agency has become a respected risk management advisory and insurance group, known for its expertise, thoroughness, responsiveness, and signature “can-do” approach. Under Greg’s leadership, the team continues to ensure that client service stays paramount, solutions are personally crafted, and relationships are built on clarity and care.

Kristin Bailey

Co-Owner and President

Kristin Bailey joined Greg Howes in 2017 after a successful 15-year career with Bank of America Merrill Lynch. Raised in Carlisle, Massachusetts, she comes from a family whose ties to the Boston insurance industry date back to 1957.

Kristin brought a rare blend of financial acumen, business leadership, and deep personal connection to our community that quickly made her an invaluable part of our agency. She transitioned from client service to operations leadership, earning a promotion to vice president and chief operating officer.

In 2020, Kristin became an agency partner and was named president. Under her direction, our firm has continued to grow and evolve, culminating in the 2025 rebranding to Bailey Howes Insurance Group. Her commitment to building lasting client relationships, nurturing strategic partnerships, and upholding the agency’s legacy of personalized service ensures that our reputation for integrity will continue for generations to come.