Commercial Underwriter / Business Systems Analyst

Wynward Insurance Group - Winnipeg, MB (30+ days ago)

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Location: Winnipeg, MB

“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 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, with the ability to prioritize and consistently meet deadlines.

Reporting to the Manager, Underwriting & Business Processes, the Commercial Underwriter / Business Systems Analystis a Head Office position that will be responsible for assisting and supporting the project team in the scoping and configuration efforts surrounding the implementation of our new back office system (BOS). The primary areas of focus include underwriting and issuing processes as they relate to the BOS implementation.


  • A key member of the BOS Project Team when it comes to requirement gathering, configuration, quality assurance testing, training and implementation
  • Actively participates in the design and build phases to provide clarification and support for the approved project requirements
  • Works with colleagues and the BOS Project Team to meet established target dates and completion of activities/deliverables under changing conditions
  • Assists the BOS Project Team in executing the project in accordance to the established project and governance plans
  • Works with the BOS Project Team to ensure information gathering and business processes are in line with business requirements and best practices


  • A minimum of 5 years of Commercial Property & Casualty underwriting experience
  • Familiarity with risk management and quality assurance control
  • Ability to coordinate multiple activities while keeping deadline oriented
  • Strong analytical, assessment, decision-making, and organizational skills
  • Excellent oral and written communication skills
  • Strong aptitude in both business and technology
  • Completion of or working towards a CIP or FCIP designation an asset
  • University or College Degree, preferably in a business or analytical discipline an asset

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

Job Type: Full-time


  • Insurance: 5 years