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Regional Underwriter And Trainer

Posted on March 6, 2026 by Westland Insurance Group

  • Full Time

Regional Underwriter And Trainer
We’re searching for a Dedicated Regional Underwriter and Trainer. Are you searching for new possibilities?
Expected Compensation: The expected hourly hiring range for this role is $29.00 to $36.50 based on a 35-hour work week. Actual offered salary will depend on the successful candidate’s qualifications and experience, as well as market conditions for the role, and internal equity.
Westland is committed to continuous learning where employees can grow their potential and write the stories of their careers. Financial assistance is available for approved work-related training/development courses leading to certification, and programs that offer professional development, including seminars and conferences.

Discover what’s possible, with Westland.
The Westland story is all about growth, and that means plenty of possibility for everyone on our team. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. As we continue to open new doors, we're inviting amazing people like you to join us.
As a Regional Underwriter and trainer, you inspire and guide teams to support our clients, increase retention, and expand our growth across Canada.
Interested in learning more?

Why you'll love Westland:
  • An open, flexible and welcoming workplace
  • Plenty of opportunities to grow and learn
  • Autonomy to own your own success
  • Be part of our inclusive culture, alongside an extraordinarily talented community of people with a wide variety of backgrounds
  • Total rewards program that takes care of your financial, physical, and mental health
  • Flexible paid Commemorative Days to celebrate days important to you
  • Amplifying Communities, a program to support causes that matter most to our employees
Why we’ll love You:
  • Self-starter with strong analytical skills and a sharp eye for the details
  • Solid communications skills with a natural ability to build authentic relationships
  • Strong background in underwriting principles and working knowledge of insurance software (Acturis, WIP and WIES)
  • Effective trainer with the ability to create and adapt to a variety of presentation settings and cohorts
  • Minimum two years’ experience in Regional Underwriting with a Insurance Broker Level 2 license
Once here, you'll:
  • Work collaboratively with Branch Managers and Insurance Advisors to provide crucial product training to support our growth strategy
  • Coach advisors to continually improve overall underwriting quality and increase sales
  • Provide support for Acturis and WIES processing and invoicing inquiries
#LI-VH1
#LI-Hybrid

Want to get to know each other better? Send your resume our way.

You belong here
We strive to be much more than a great place to work. Here, you join a collective of incredibly vibrant, purpose driven, and open-minded people. Every day, Westland proves that building a great business means taking care of communities, clients, and each other with equal commitment. You will be supported and respected for who you are and for the voice you add to the conversation.

At Westland, you will feel the power of community. Westland Insurance Ltd. is an inclusive organization that values diversity in its workforce. We listen, champion equity and diversity, and create safe welcoming spaces where everyone has a voice and is free to be themselves. Westland Insurance Ltd. encourages applications from all qualified individuals and will accommodate applicants' disability-related needs, up to the point of undue hardship, throughout all stages of the recruitment and selection process.

If you require a disability-related accommodation in order to participate in the recruitment process, please contact the recruitment team by email at careers@westlandinsurance.ca

Advertised until:
April 5, 2026


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