Intermediate Commercial Claims Adjuster - Greater Toronto Area Remote


Location: Greater Toronto Area

“Times like this 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, located in Winnipeg MB, with additional offices in Halifax NS, London ON, and Regina SK.


We are looking to add an experienced Intermediate Commercial Claims Adjuster to our Claims team. This person will be responsible for the investigation and adjusting of commercial property claims within the greater Toronto area.

As a fully remote employee, it is important for the successful candidate to be customer focused, resourceful, and an independent self-starter, with flexibility regarding working hours and availability to travel extensively within the assigned region.

The position can be tailored to include liability claims if the successful candidate has the appropriate experience and background.

Key Accountabilities:

Investigate scope, confirm coverage, negotiate settlement and recovery, and conduct reporting and documentation on a task assignment basis for substantial and complex claims in accordance with established guidelines.

  • Conduct field investigations of claims through contact with insurers, claimants, witnesses, other carriers, physicians, contractors, lawyers, etc.
  • Secure loss location and evidence.
  • Evaluate, analyze, and interpret policy wordings, including recognizing policy exclusions, in order to assist with the determination of coverage applicable to the loss.
  • Determine and obtain the type of required documentation necessary to support claims in accordance with company policy, as well as federal, provincial, and local regulations.

Ensure the accurate and efficient payment of claims in accordance with legislative requirements.

  • Review available information and assist with the recommendation of appropriate reserves, payments or recovery, negotiation, or declination.

Develop relationships and work with other departments such as underwriting to meet business goals. This includes sending emails to underwriting notifying them of potential risks/hazards.

Understand and apply standard operating procedures towards compliance, internal control and operational risk controls in accordance with national and regulatory standards and policies.

Mentor and train less experienced claims and support staff.

  • Assist in the development and implementation of training programs.
  • Participate in the training and development of other claims staff members, and provide technical expertise and advice regarding products, systems, and processes.

Skill/Behavior Requirements:

  • Ability to understand and interpret relatively complex insurance contracts and changes in the interpretation as a result of case or statutory law.
  • Ability to demonstrate patience, empathy and understanding in dealings with customers.
  • Ability to provide prompt, efficient, and courteous service to all parties involved.
  • Ability to assess liability and understand case law developments in the jurisdiction.
  • Demonstrated negotiation skills.
  • Strong analytical, problem-solving skills, investigative, and decision-making skills.
  • Demonstrated report-writing skills, including an orientation toward detail and precision.
  • Able to plan, organize, and manage multiple demands and changing priorities.
  • Demonstrated ability to work well as a team player or independent contributor; Self-motivated.
  • Strong leadership skills and interpersonal skills.
  • Excellent communication (both oral and written) skills to explain processes and terms.


  • Minimum 5 years of relevant experience handling commercial property claims
  • Preference for candidates with a university or college degree, CIP designation completed or in process
  • Previous experience working in a remote environment (preferred)
  • On-going commitment to education and training
  • Strong analytical, assessment, decision-making, and organizational skills
  • Ability to balance investigative requirements with customer service expectations
  • Excellent oral and written communication skills
  • Valid driver’s license and an excellent driving record.
  • Must be self-motivated, team player with a positive attitude
  • Fluently bilingual (English / French) is a definite 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.

Wynward is proud to be an equal opportunity employer.

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