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, CPCU

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, CISR, CPIA

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.

What You Can Expect from Us

We are committed to providing an insurance experience defined by exceptional service, accountability, and genuine care.

We prioritize paying attention to every detail of your life.

We make the insurance process easy for you.

We pride ourselves in providing consistent, responsive service.

We stay ahead of your risks and manage them proactively.

We are always available to provide thoughtful, personalized advice.

We are invested in building lifelong, collaborative partnerships.

Hear From Our Clients

What Makes the Bailey Howes Insurance Experience Different?

    
 
 
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   Lee-Ann Norman 
 8 September 2025
 
 
 Trustindex verifies that the original source of the review is Google. Catherine Washington is excellent to work with!  She has helped me with my personal insurance questions as well as preparing to open a business questions.
  
 
      Posted on Google  
   
   Anders Beer 
 26 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. I have had nothing but good experiences with Howes insurance group. Greg Howes, Traci Madigan, and Mike Umano were all really responsive and articulate when it came to finding the right insurance and answering questions regarding home, umbrella, and auto policies.

I have had plenty of questions for all of the people I named, and every one of them has been really insightful and articulate. Most recently I asked about those consumer insurance policies that are often sold by retailers and what differentiates them from the coverage under our homeowners policy. Mike was kind enough to go into detail about it and I really appreciated his objective breakdown on how the coverage works.

Keep up the fine work, Howes Insurance Group :)
  
 
      Posted on Google  
   
   Robert Stemple 
 18 August 2025
 
 
 Trustindex verifies that the original source of the review is Google. Over 30 years of helpful, quick answers. They treat you as friends not customers😀👍👍👍
  
 
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   Roger Beatty 
 4 December 2024
 
 
 Trustindex verifies that the original source of the review is Google. Howes is a small agency staffed with highly knowledgeable insurance professionals -- they're large enough to attract and retain experienced pros, and small enough to ensure personal contact in all business interactions. No voice mail maze, no call center, no chatbots -- they'll answer the phone directly, or call you back same day. When I call, I usually reach somebody I already know on my first attempt. I've been with them for years, and they've always done a great job.
  
 
      Posted on Google  
   
   Irwin Hipsman 
 26 November 2024
 
 
 Trustindex verifies that the original source of the review is Google. We have both our home and auto with Howes Insurance. Recently, we had a very challenging purchase of an auto and damage to our house. In both situations they were incredibly helpful and reassuring. Highly recommend the team and a special shout out to Traci.
  
 
      Posted on Google  
   
   Gregory Ladd 
 30 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The personalized service and breath of offerings really makes a difference!
  
 
      Posted on Google  
   
   Steve Neff 
 3 October 2024
 
 
 Trustindex verifies that the original source of the review is Google. The Howes team has been a valued services and support team. They are knowledgeable, proactive and we have a comprehensive umbrella policy for multiple properties, cars etc. Also a big shout out to our Account Manager Jennifer Drasser.
  
 
      Posted on Google  
   
   Jack 
 23 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. From the moment I placed a call to Greg Howes, I knew I was in good hands. He took the time to explain every detail of the half dozen properties and autos I wanted to insure and came in less than other quotes at a higher level of coverage! Jennifer continued the process with countless phone conversations and emails. She's knowledgeable, patient, helpful, empathetic, experienced and extremely affable. I can't say enough and am grateful to have found Howes Insurance Group. You will be too!
  
 
      Posted on Google  
   
   Sylvia Diaz 
 6 September 2024
 
 
 Trustindex verifies that the original source of the review is Google. It's' a comfort for me to know that I have The Howe's Insurance Group behind me to help me navigate the complex business of insurance.

The Howe's Insurance Group is very responsive to my questions and needs. Together, we review, my family's insurance needs every year.