Winnipeg, MB


Location: Winnipeg, MB Head Office Branch

“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 a subsidiary of James Richardson & Sons Ltd and 100% Canadian owned, conducting business in all 10 provinces and 3 territories.  Our Head Office and Branch is located in Winnipeg MB, with additional offices in Halifax NS, London ON, and Regina SK.


We are looking for a bright, energetic person to assist in our policy issuance department who is meticulous, customer focused and has the ability to prioritize and consistently meet deadlines.

Reporting to the Underwriting Technical Assistant Supervisor, the Underwriting Technical Assistant will be responsible for processing clerical work for the Underwriting Department.


  • Data processing and assembling of Head Office new business, renewals, endorsements and cancellations of insurance policies.
  • A key focus will be on Next Wave Cannabis Coverage policy entry.
  • Entering policies accurately in a timely manner.
  • Providing coaching, mentorship and guidance to fellow Head Office Underwriting Assistants.
  • Reviewing and auditing of Head Office policy entries.
  • BOS Enterprise testing.
  • Scanning, printing, faxing and emailing documents.
  • Backup reception and mail room duties.


  • A minimum of 1 year of Commercial P&C Underwriting Technical Assistant experience required.
  • Enhanced ability with MS Office software as well as keyboarding and computer skills
  • Must have high attention to detail & able to perform work accurately
  • Excellent time management
  • Good communication skills, both oral & written
  • Able to establish and maintain positive working relationships with other team members
  • Completion of Grade 12 education

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 re-freshing, 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.  To encourage you to maximize your potential we provide continuing training and education opportunities. 

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


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