Wynward : Everything you need to know

Wynward: Everything you need to know
Founded: 1920

Type of services: Commercial property & casualty insurance

Offices: Winnipeg, MB; Regina, SK; London, ON; Halifax, NS

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
1920: Wynward is founded as Grain Insurance & Guarantee

2013: Wynward rebrands to reflect diverse product and service offerings

2015: James Richardson & Sons acquires Wynward Insurance Group

2017: Wynward partners with Next Wave Insurance and enters the cannabis insurance space

2019: Wynward Insurance Group maintains its support of the Broker Identity Program (BIP) at the Full Partner level

Key people as of 2019
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, when the company won the award in 2016. “To be recognized for a third year in a row 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