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

For 3 consecutive years, Wynward Insurance has won the award as one of Canada’s Top 100 Small and Medium Employers. We have also been recognized among the best 25 Employers of Manitoba in 2016.

Wynward is a very rewarding company to work for. Wynward is a company that values their employees as well as their customers and broker partners. We are continually growing and evolving in the industry. I feel honored and proud to be a part of such an amazing company. You feel like you are part of a family – a work family.

Michelle Anderson, Commercial Underwriter Regina Branch - Wynward Insurance Group

I love my job. I am excited to come to work each day. The Senior Leadership Team’s guidance and positive re-enforcement makes coming to work enjoyable. Wynward = teamwork. Advice is as close as the person sitting next to you. Everyone wants to help you succeed. The culture here at Wynward is welcoming, warm and friendly. You truly feel like you are part of a great team, because you are.

Greg Bowey Manager, Loss Prevention - Wynward Insurance Group

What I enjoy most about working at Wynward is the amazing team of people. I have made lifelong friends with some who I frequently see outside of work. I’ve grown up here - I’ve gotten married, had children and plan on being here for a long time. It’s refreshing to see the new changes we are implementing to make us a front runner in our industry. I get the chance to laugh, share stories, work as a team, laugh some more, and of course work hard.

Amanda Scaletta, Claims Examiner - Wynward Insurance Group

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. This is promoted by offering flex time. 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.

Innovation, Growth and Forward Thinking

Our people make us stronger in everything we do.

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.

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