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More About Us

We take our commitment to our customers in earnest, served by our family of dedicated employees and the trusted insurance companies we represent. Crossroads Insurance committed to ensuring that you and your family are protected. We work with you to understand your insurance requirements, helping you to identify and analyze your exposure to loss, and then selecting the best methods possible for dealing with those exposures. We find providers who offer you the broadest possible coverage for your needs. Should a loss occur, we represent you during the claims process as your advocate, ensuring that you and your family are properly cared for and receive the benefits you're owed. The value of an insurance product is not based solely on its price – it's also reflected in the service you receive, how losses are covered, and if your expectations are met.

Our Mission

We are here to support our clients as they take steps towards protecting what matters to them. We set ourselves apart by committing to personal relationships so our clients will never feel like “just a number”. Our focus is providing the best customer experience. We accomplish this through simplifying insurance by educating, guiding and providing choice.

Meet The Team

T.J. McRedmond, CAIB


T.J. started his career in the insurance industry with Crossroads Insurance in 1988 after attending the Universities of Winnipeg and Manitoba. He obtained his Canadian Accredited Insurance Broker designation in 1996. In 1997, T.J. purchased the shares of Crossroads Insurance and became President. Over the years T.J. has been very involved with the Insurance Brokers Association of Manitoba serving on various committees including Past Chair of the Young Broker Network as well as serving as a Director on the IBAM Board. T.J. lives in East St. Paul with his wife and children.

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Tony McRedmond

Vice President

In 1967 Tony immigrated to Canada from Waterford Ireland.  At the age of 27 he founded Crossroads Insurance, working out of his home with his wife Dianne.  Tony has 4 children, 8 grand children and 3 great grandchildren.  Now that he is semi-retired he gets to enjoy his favourite hobbies such as golfing, gardening, reading and music.   

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Nella DiGirolamo, CAIB

Residential Insurance Manager

After completing her diploma in Business Administration at Red River Community College in 1994, a friend approached Nella to see if she wanted to work at a little agency on Corydon and on January 2nd, 1995 she began her career in the Insurance Industry. For the past 16 years Nella has enjoyed her time at Crossroads Insurance (her words, not ours!). Within this time she contributed to all the different elements of the business.

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The Crossroads Insurance Advantage

We shop for you so you can be confident you are receiving the most competitive rates.

Convenient locations in the north and south of Winnipeg

Family owned, Manitoban company

24-Hour claim service

Multi-cultural team that can do business 10+ languages

We offer choice and guidance above all else

40+ years in the business

Support and advocacy in the event of a claim