• Skip to main content
  • Skip to secondary menu
  • Skip to primary sidebar
  • Skip to footer
  • Contact Us
  • Post A Job

Agency Checklists

Massachusetts Insurance News & Job Opportunities

  • AC Interviews
  • Agency M&A
  • Career News
  • CAR News
  • DOI News
  • Coverage Cases
  • Innovation
  • InsurOp-Eds
  • AC Podcast
You are here: Home / Agency Perpetuations, Valuations & Sales / Agency Mergers & Acquisitions / Risk Strategies Acquires California’s Winter Group, Inc.

Risk Strategies Acquires California’s Winter Group, Inc.

July 16, 2019 by AC Editor

Massagents insurance acquisitions, Risk StrategiesThe Boston-based brokerage firm’s buying spree continues

Risk Strategies continues its national expansion with another acquisition this summer in San Diego. The Boston-based brokerage firm announced the acquisition of Winter Group, Inc., a specialty insurance program manager focused on the trucking industry, particularly in cross-border transportation risks. Further terms of the agreement were not disclosed.

“Strong, continued economic growth is driving rapid expansion in the U.S. transportation sector at a time when technological and road safety advances are creating new opportunities for differentiation and specialization,” said Matthew Power, Senior Managing Director (Wholesale) of Risk Strategies. “More than ever, brokers serving this industry need more than access, they need a specialist like Winter Group on their side.”

A presence in eight states

A beneficial addition to Risk Strategies growth within the transportation industry, Winter Group serves over 17,000 through its office locations in eight states: California, Texas, Florida, Washington, South Carolina, Atlanta, North Carolina and Ohio. In addition to its national presence, the Group also is considered a market leader with respect to NAFTA transportation risk management and compliance and acts as a program administrator for several national trucking associations

“Risk Strategies is a highly collaborative and innovative firm,” said Phillip Winter, Managing Director of Winter Group. “Its focus on distinctly differentiated niche areas of our industry, and an acquisition strategy centered on specialty wholesale organizations, is a perfect foundation on which our team, customers and stakeholders can grow and thrive.”

Risk Strategies’ financial backing from private equity firm fuels growth

Founded in 1997, Risk Strategies has grown over the last 18 years to become one of the top 20 largest insurance brokerage firms in the U.S. The privately-held Risk Strategies focuses on middle and upper-middle market commercial and high-net-worth clients with its vertical industry expertise including healthcare, higher education, manufacturing, professional liability, construction, entertainment, fine arts, private equity, private client and real estate.

In October of 2014 Risk Strategies acquired the DeWitt Stern Group, greatly expanding its Private Client practices into New York City, Chicago, Los Angeles, and Sacramento. In July 2015, it went on to acquire the Burlingame, California-based MacCorkle Insurance Services giving it a foothold in the San Francisco area. In October 2015, the firm established a new Private Client practice in the Southern states of Tennessee, Georgia, and Alabama via its previous acquisition of the Crow Friedman Group.

In November 2015, Kelso & Co., one of the oldest and most established firms in the private equity industry as well as a leading investor in the insurance sector, announced that it had acquired a majority stake in Risk Strategies.

Primary Sidebar

Job Board

  • NEW! Commercial Insurance Manager (SalemFive)
  • NEW! FAST Auto Appraiser III (N&D)
  • NEW! REMOTE: Senior Marketing Representative (N&D)
  • BOSTON: Commercial Lines Account Manager (LORE)
  • WOBURN: Sr. Personal Insurance Account Manager (Salem Five)
  • QUINCY: AVP Sales & Marketing (Arbella)
  • YARMOUTH: Commercial Lines Account Manager (Pioneer)
  • SOUTHBOROUGH: President & CEO (Hospitality Insurance Group)
  • SOUTHBOROUGH: Commercial Lines Small Business Account Manager (Fitts)
  • WAKEFIELD: Account Manager – Personal Lines (Hartshorne & Curley)
  • WOBURN: Senior Commercial Lines Account Manager (SalemFive)
  • HOLYOKE: Commercial Lines Account Manager Insurance (Chase Clark Stewart & Fontana Agency)

Career News

Professional headshot of a smiling man in a blue suit against a dark gray background.

Jeffrey C. Johnston Named NAIC Chief Executive Officer 

Patriot Growth Insurance Services appoints Chi Vo as Senior Vice President of Operations to lead agency integration and growth strategy

Chi Vo Joins Patriot Growth Insurance Services as Senior Vice President of Operations

Arbella Insurance leadership transition Bob Bizak retirement Andrew O’Donoghue promotion

Arbella Insurance Group Announces Retirement of Bob Bizak, Executive Vice President of Sales & Marketing 

Risk Strategies founder Michael Christian

King Risk Partners Announces Addition of Michael Christian to Its Board of Directors

View All

Listen Now

Sponsor

Interviews

From Nuptials, Tickets, and Taxes to Trusted Advisor: One Agency’s Unique Path to P&C Success

A Conversation with Evan Silverio, President & CEO of Silverio Insurance Group

Deland, Gibson Celebrates 125 Years: A Conversation with CEO Chip Gibson

The Fourth-Generation Family-Owned Agency is Based in Wellesley

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual | Agency Checklists

Talking with Richard Welch: Growth and Innovation at Hospitality Mutual

Mr. Welch is CEO of Massachusetts-based Hospitality Insurance Group

Born and Bred in the Bay State: The Special Agent Story

Our Latest Agency Interview is with the Founder & President of Special Agent

A Conversation with Daniel C. Bridge – The 2023 Insurance Professional of the Year

Daniel Bridge is Board Chair, President, and CEO of Vermont Mutual Insurance Group

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Making The Leap From Corporate to Entrepreneur: Nadeen Vella On Building NaVella Insurance From Scratch

Our latest Agency Interview is with Nadeen Vella, the founder and owner of a virtual scratch independent agency.

View All

InsurOp-Eds

InsurOp-Ed: Understanding The Insurance Supply Chain

By Peter MacDonald

Agency Checklists, MA Insurance News, Mass. Insurance News, Mass. Insurance Coverage disputes

InsurOp-Ed: 3 Sources of Coverage Gaps That Lead to Claim Disputes

By Bill Wilson

InSurOp-Ed: Another Cautionary Tale of Underinsurance

InSurOp-Ed: Another Cautionary Tale of Underinsurance

By Bill Wilson

InsurOp-Ed: Time to Make Government Action Exclusions More Equitable?

By Bill Wilson

View All

In Memoriam

Eric Cioppa was Maine's Superintendent of Insurance from 2011 until 2022.

In Memoriam: Eric Cioppa, 1958-2026

In Memoriam: David H. Knight, 1936-2026

In Memoriam: David H. Knight, 1936-2026

In Memoriam: Saul F. Feingold, 1932-2026

In Memoriam: Saul F. Feingold, 1932-2026

Footer

Contact us

We offer a variety of ways to get help promote your company or product.

Announcements
Email Sponsorships
Partnerships
Custom Collaborations

*Affiliate Disclosure

Please note that any of Agency Checklists’ articles might contain one or more affiliate links. This means that any subsequent purchase resulting from these links may result in a commission for us, but at no additional cost to you. For example, as an Amazon Associate, Agency Checklists earns a commission from all qualifying purchases. By working with affiliates we can continue to keep Agency Checklists subscription free. Thank you for your support.

Explore Our Archives

Copyright © 2026 · Agency Checklists · All rights reserved.

Loading Comments...