Group Benefits Contract Specialist

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Date: Jan 22, 2026

Location: Kitchener, ON (Hybrid), CA Dartmouth, NS (Hybrid), CA Wawanesa, MB (Hybrid), CA Calgary, AB (Hybrid), CA Moncton, NB (Hybrid), CA North York - Toronto, ON (Hybr, CA Edmonton, AB (Hybrid), CA Ottawa, ON (Hybrid), CA Winnipeg, MB (Hybrid), CA Vancouver, BC (Hybrid), CA

Company: Wawanesa Insurance

 

Job ID: 9697 


Employment Type: Existing Role

Working Business Language: English
 

Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan. 
 

The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $58,000 - $68,000. Candidates with salary expectations outside of the range are still encouraged to apply. 

About Us
At Wawanesa, we offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Moncton, NB; Dartmouth; NS. 
 

The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,300 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. We are also proud to be recognized as one of Manitoba’s Top Employers. To learn more visit wawanesa.com. 


We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.
 

Job Overview

Reporting to the Manager, Group Insurance, the Group Contract Specialist is responsible for supporting the preparation, maintenance, and updating of group insurance contracts, booklets, and related documentation. Working closely with internal teams such as Legal, Compliance, Claims, Product, Sales, and Underwriting, this role ensures that insurance provisions are clearly, accurately, and consistently communicated to Plan Sponsors. The Group Contract Specialist also responds to routine contract-related inquiries from internal partners and external stakeholders, escalating complex matters as required.
 

Job Responsibilities

  • Prepare, update, and review and audit group benefits contracts, booklets, and related documentation using approved templates and standard wording to ensure accuracy, consistency, and compliance with established legal, regulatory, and company requirements.
  • Collaborate with legal and compliance teams to incorporate required changes and clarifications into contract and booklet language.
  • Maintain contract-related records, amendments, and document versions to ensure materials are current, accurate, and properly archived.
  • Support updates to benefit provisions, eligibility criteria, and standard clauses as directed.
  • Apply regulatory and compliance updates to contracts and booklets as communicated by legal or compliance teams, ensuring alignment with applicable legislation and internal policies.
  • Liaise with internal partners including Legal, Compliance, Sales, Underwriting, Claims, and Product teams to support accurate contract documentation and interpretation.
  • Respond to routine contract‑related inquiries from Plan Sponsors, brokers, and field staff, escalating complex or non‑standard issues as appropriate.
  • Assist with documentation updates related to benefit plan changes, renewals, and new product initiatives, ensuring assigned timelines and deliverables are met.
  • Perform quality checks on contracts and booklets to ensure accuracy, completeness, and adherence to document standards.
  • Develop and maintain working knowledge of group insurance products and contract structures, including health, dental, life, and disability benefits.
  • Provide basic guidance to internal partners regarding standard contract wording, documentation processes, and interpretations.

Qualifications

  • Relevant post‑secondary education in a related field.
  • 3+ years of experience in the group insurance industry or a related role.
  • Ability to accurately interpret and apply group insurance contract and booklet wording in accordance with benefit provisions, regulatory requirements, and company guidelines.
  • Working knowledge of group insurance products, including health, dental, life, and disability benefits.
  • Strong attention to detail with the ability to accurately interpret and apply contract terms.
  • Demonstrated excellent written and verbal communication skills with  internal and external stakeholders.
  • Demonstrated critical thinking, problem solving, and analytical skills.
  • Strong deadline and time management within a fast-paced environment.
  • Ability to work independently while contributing effectively within a team simultaneously.
  • Bilingual in French is considered an asset.


Diversity Equity, Inclusion & Belonging

At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.

We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas. 
 

We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to jobs@wawanesa.com.
 

All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.

Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.