Wynward : Everything you need to know

Wynward: Everything you need to know

Headquarters address

1240 One Lombard Place, Winnipeg, Manitoba R3B 0V9, Canada

Year established


Size (employees)

Office locations Winnipeg, MB; Regina, SK; London, ON; Halifax, NS
Underwriting expertise Commercial property & casualty insurance
Key people Darryl Levy (president & CEO)
Financial strength rating A (Excellent) – A.M. Best

About Wynward

Wynward Insurance Group is a commercial P&C carrier headquartered in Winnipeg, Manitoba. The company got its start in 1920, when a group of prairie grain companies that were unhappy with the premiums they were being charged for fire insurance on their grain elevators decided to found their own insurance company, in the hope of pressuring underwriters to reduce premiums. While the strategy didn’t work, the group identified a key need in the marketplace, and so, Grain Insurance & Guarantee was born.

Over the past century, Wynward has expanded its business, and today serves customers in all provinces and territories via a strong broker network. The carrier rebranded itself in 2013 to address the fact that it now provides far more than grain insurance, and is also a wholly-owned subsidiary of Winnipeg-based James Richardson & Sons Limited, as of 2015.

Wynward’s expertise ranges from the amusement industry to faith-based organizations, manufacturing to wellness and fitness, while solutions address a variety of risks, from cyber to equipment breakdown, though Wynward is also focused on preventing disasters where possible through risk management and loss control.

Wynward in the news

2015: James Richardson & Sons acquires Wynward Insurance Group
2015: Wynward Insurance: the obvious solution for Canadian franchise owners
2016: Fun is a serious business: Wynward is a leader in the amusement industry
2016: Wynward Insurance Group wins honour third year running
2017: Wynward Insurance continues to support broker identity network
2017: Gregg Hanson becomes Chairman of Wynward Insurance Group
2019: Wynward Insurance Group maintains its support of the Broker Identity Program (BIP) at the Full Partner level
2019: Wynward CEO discusses why disruption “is actually a good thing for incumbent legacy insurers in Canada”
2021: Wynward Insurance Group remains a full partner of IBAC’s broker advertising campaign
2022: Wynward Insurance Group affirms support for IBAC's national broker campaign

Key people

Darryl Levy, president and chief executive officer
Levy had a diverse career before coming to Wynward, working at telecom titan Rogers and the United Way of Winnipeg. He’s been at the company for more than eight years as president and CEO, jumping on board in 2011.

Gregg Hanson, chairman of the board of Wynward Insurance Group
Hanson is an experienced insurance executive, having served as president and chief executive officer of Wawanesa Insurance. He is also a director of Wynward Insurance Group, as well as Wynward’s parent company, James Richardson & Sons. He joined Wawanesa in 1979 and made his way through the company ranks, before being made president and chief executive officer of Wawanesa in 1992. He held this position until retiring in 2007. Hanson has served on many charitable organization boards, including being chairman of The Winnipeg Foundation, chairman of finance for the 1999 Pan American Games in Winnipeg, and several United Way of Winnipeg committees, alongside others.


Wynward has consistently been named one of the nation’s best places to work, after being recognized multiple years in a row as one of Canada’s Top 100 Small & Medium Employers by Mediacorp Canada Inc.

“Our people are what make the difference at Wynward,” said Levy. “To be recognized… is an outstanding achievement for all of our Wynward team members across Canada.  It is a testament to their passion, hard work and daily commitment to providing innovative and best-in-class broker and customer solutions.”

Wynward : In the news