Senior Underwriter (New Business) - Manitoba Remote

Senior Underwriter (New Business)

Location: Winnipeg Branch – Manitoba Region

“Times like these call for a PERFECT FIT”

Wynward Insurance Group is a progressive company known for developing innovative insurance products and services for Canadian business and our broker partners from coast to coast.

Founded in 1920, we are proud to be 100% Canadian owned, conducting business in all 10 provinces and 3 territories. Our Head Office is located in Winnipeg MB, with additional offices in Halifax NS, London ON, and Regina SK.


We are looking for a self-motivated insurance professional who is business minded, results driven and customer focused.

Reporting to the Regional Director, BC, AB, MB, NW Ontario, the Business Development Representative will be responsible for the profitable growth of Wynward Insurance Group’s position within the Manitoba region with an identified portfolio of brokers through a combination of sound underwriting and business development skills.

This individual will be based in Manitoba, preferably the Winnipeg area. Office attendance is not required and this individual can be fully remote. However, there is an opportunity to enjoy the benefits of an office culture in downtown Winnipeg when desired.


  • Identify and drive a distribution strategy which supports long term growth and profitability in a new market, by working collaboratively with the Underwriting and Sales leadership team
  • Quote and negotiate incremental business via selecting, assessing and pricing risk with proven underwriting techniques
  • Provide exceptional service to identified broker partners targeted for growth
  • Develop and maintain strong broker relationships through regular visits and communication
  • Work closely with the Loss Prevention team to understand risk management trends
  • Collaborate with Branch Management in the development and coaching of junior underwriting team members
  • Liaison with the Marketing/Business Development team in gathering and communicating competitive market intelligence
  • Represent Wynward Insurance Group at various industry or trade functions to drive brand awareness.


  • 7 – 10 years of Commercial Underwriting experience
  • Completion of, or working towards CIP / CRM designations
  • A proven track record of exceeding sales and development targets
  • Ability to work independently
  • An entrepreneurial spirit and a desire to succeed
  • Well organized, self-starter with excellent time management skills

We pride ourselves in working collaboratively with our team members in creating a workplace rooted in the principles of integrity, passion and hard work. Our team members describe Wynward as refreshing, progressive, and innovative with an engaging team-first environment.

Wynward Insurance Group offers a competitive salary, an exceptional benefits package including health and dental benefits, an educational reimbursement plan and a competitive pension plan. We support and reward high performance with a competitive bonus policy. This position also provides a car allowance. To encourage you to maximize your potential we provide continuing training and education opportunities.

To learn more about our award-winning organization, please visit