Please ensure Javascript is enabled for purposes of website accessibility
Our Agency

Steering & Securing Your Course for Insurance Since 1877 

HISTORY

Located on Route 28, off exit 12 on I-495, the residents of Southeastern Massachusetts have enjoyed over 140 years of professional and trustworthy customer service. Established in 1877, our agency has always been a family-owned business. T.M. Ryder Insurance was founded by Thomas M. Ryder and succeeded by his nephew, Charles Ryder at the turn of the century. Ralph W. Maddigan went to work for Charles in the early 1900’s and bought the agency from him in 1917. Ralph W. Maddigan Jr. joined the agency after serving in WWII. In 1972, Ralph W. “Skip” Maddigan III joined the agency, and it was incorporated in 1973. Like his father and grandfather, Skip valued customer service and integrity. Kira and Kristi (both Skip’s daughters) joined the agency in 2011 and 2015, respectively and continue to carry on that tradition while bringing the business into the 21st century. Both are 4th generation in the family to be in the business. In 2017, T.M. Ryder celebrated 100 years of ownership and management in the Maddigan family.

OUR TEAM

Judi

info@tmryder.com

Judi, the incumbent president, is Skip’s surviving spouse and has been an officer of the agency for the past 3 decades. She is the mother of 3, including daughters Kira and Kristi. Judi and is an avid fan of the ballet and loves spending time with family, especially her grandchildren.

Kira – Principal/CFO

Kira is the oldest daughter of Skip and the fourth generation of her family to work at the agency. She joined the team in January 2011 and brings a strong background in marketing and sales. A proud Babson College alumna, she was a multi‑sport athlete, playing soccer, rugby, and ice hockey.

Kira lives locally with her two children, two dogs, and two sugar gliders. She loves reading, traveling, great food, and still enjoys playing soccer—she even helps run the local women’s league. Deeply involved in the community, Kira participates in business networking on behalf of the agency, volunteers with the Middleboro YMCA, and coaches for FreeLake United Youth Soccer. She is a licensed producer with extensive experience in commercial lines.

Kristi – Principal/CMO

Kristi joined our team in November 2015. She is also the daughter of Skip and 4th generation in the family to work at the agency. A Saint Leo University alumna, she also has a background in marketing/sales. Kristi enjoys living in beautiful Onset with her husband, daughter, and dog. She is an avid New England Sports fan and enjoys playing all sports, including soccer and golf. Kristi is also a licensed producer and works closely with the personal and commercial sales/service teams. Kristi is also involved in her community, including business networking, serving on the board for the Cape Cod Canal Region Chamber, and volunteering with the Onset Bay Association.

John – Director of Operations

Since entering the insurance industry in 2003, John has built a career focused on operational excellence and personal risk management. He joined the T.M. Ryder team in 2025, providing expert guidance and strategic support to the agency. John balances his professional life with a love for family and community; he lives in the area with his wife, three kids, and their dog. When he isn’t working, he is often coaching youth baseball, playing golf, or attending concerts.

Matthew – Licensed Agent Personal Lines

Matthew is a Personal Lines Insurance Producer that specializes in helping individuals and families protect what matters most. Matt works closely with clients to understand their unique needs, clearly explain coverage options, and create customized insurance solutions for auto, home, renters, umbrella, and recreational policies.

 

Matt is passionate about building long-term relationships, providing proactive service, and making insurance simple, transparent, and stress-free. Whether it’s finding the right coverage, identifying gaps, or adjusting policies as life changes, Matt’s goal is to be a trusted resource his clients can rely on.

Danielle – Licensed Agent Commercial Lines

Danielle is a Commercial Lines Insurance Agent with over five years of experience at T.M. Ryder, focused on helping businesses find the right coverage without the hassle. She enjoys working closely with clients to understand how their business operates and making sure everything is properly protected. Her goal is to make the process as easy as possible and is always available to answer any questions along the way.

Outside of work, Danielle enjoys cooking, baking, and going to Seekonk Speedway with her husband and son. Danielle is also a member of a military vehicle collector club, where she participates in local parades driving vintage military vehicles.

Matt is passionate about building long-term relationships, providing proactive service, and making insurance simple, transparent, and stress-free. Whether it’s finding the right coverage, identifying gaps, or adjusting policies as life changes, Matt’s goal is to be a trusted resource his clients can rely on.

Kelly – Personal Lines Client Service Specialist (A-L)

Kelly has been a proud member of the T.M. Ryder team since 2000, with over four decades of experience in the insurance industry, having started her career in 1980. She has remained committed to providing attentive and friendly service to her clients.

Outside of work, Kelly enjoys spending quality time with her three children and especially three grandsons, who keep life fun and busy. She also loves crafting and shopping in her free time.

Jenny – Personal Lines Client Service Specialist (M-Z)

Jenny has been with the agency since 2014 where she utilizes her extensive experience from the auto industry. She is dedicated to building lasting relationships and helping clients understand their coverage. When she is not in the office, Jenny enjoys nothing more than spending time with family, friends, and being at the beach.

AGENCY AFFILIATIONS

 

  • Cranberry Country Chamber of Commerce
  • Cape Cod Canal Region Chamber of Commerce
  • Networking Group USA
  • Power Hour Networking Group
  • Massachusetts Association of Insurance Agents
  • Professional Insurance Agents
  • Independent Insurance Agents & Brokers of America, Inc.

OUR COMMUNITY

T.M. Ryder has been giving back and supporting the community that we insure for decades. Below is a list of several charities and causes we have donated to most recently. Please don’t hesitate to inquire with one of the members of our marketing team above. Thank you.

Giving & Community Involvement:

Middleboro Krazy Days

Middleboro Youth Building

Old Colony YMCA – Middleboro

Oak Point Homeowners Scholarship Association

Wareham Gatemen Baseball

Freetown Lakeville Youth Soccer

Middleboro High School Athletics

Wareham High School DECA

Onset Bay Association

Freetown Lakeville Women’s Soccer League

St. Vincent de Paul Food Pantry

Lakeville Police Association

Middleboro Firefighters

S.E.A.L. Foundation

~ Steering & Securing Your Course for Insurance Since 1877 ~

– T.M. Ryder Insurance

Get a free quote to create your desired insurance.

Contact us

Drop files here or
Max. file size: 1 GB.