Wynward Insurance Group

Integrity. Passion. Respect.

Do you share the same values? Find your perfect career fit with us.

Great results come from great teamwork.

Collaboration is the key element in producing great results. We foster an environment of teamwork where everyone can feel that they are an integral part of the process. Through passion and hard work and integrity, we strive to create a sense of pride in everything we do.

A refreshing environment.

At Wynward Insurance we offer a refreshing, progressive and innovative environment. We provide an engaging atmosphere that inspires our employees. With a focus on team dynamics, there are ongoing opportunities for new ideas and a spirit of excitement about projects and initiatives. We also encourage you to keep growing by offering many training and education opportunities.

Award-Winning Workplace

Wynward is honoured to rank second among Canada’s 175 licensed property and casualty insurers on Insurance Business Magazine’s annual list of Five-Star Carriers! We have also been recognized as one of Canada’s Top 100 Small and Medium Employers for 3 consecutive years, as well as Best 25 Employers of Manitoba.

Career Opportunities:

Wynward Insurance Group | Wynward Insurance Group | Wynwardinsurance

We have a lot to offer.

There are many benefits at Wynward Insurance. Our employees enjoy a well-rounded and vibrant workplace that offers opportunities for health and well-being as well as incentives for achievement.

Competitive Benefits

At Wynward Insurance we offer a competitive salary and comprehensive benefits, including dental and health coverage, as well as a pension plan. We also cover 100% of the tuition and materials for our employees to take training related to their professional development.

Work/Life Balance

We encourage our employees to have a healthy work/life balance in order to stay engaged and productive. It’s a great way to facilitate a lifestyle that allows time for all the important things that happen in all aspects of your life.

Performance Incentives

Excellence in achievement is not only encouraged at Wynward Insurance, it’s rewarded! We recognize that everyone on our team plays an important role in the success of our business. Therefore, all employees share in our competitive bonus program that rewards high-performance.

Enjoying life at work.

Imagine a workplace where you feel a sense of camaraderie with your colleagues. At Wynward Insurance, we enjoy a comfortable business casual atmosphere, and proudly embrace diversity. We encourage open communication and support a progressive approach to professional development.