Group Benefits Service Associate

Date: Jul 10, 2026

Location: Kitchener, ON (Hybrid), CA North York - Toronto, ON (Hybr, CA

Company: Wawanesa Insurance

Employment Type

Existing Role

Work Environment: 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: Toronto (North York), ON; Kitchener, ON.

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: $70,000 - $85,000. Candidates with salary expectations outside of the range are still encouraged to apply.

About The Wawanesa Mutual Insurance Company

Founded in 1896, The Wawanesa Mutual Insurance Company is one of Canada’s largest mutual insurers, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.

Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at 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

We are seeking a dedicated Service Associate to provide direct support to our Regional Sales Manager as the primary point of contact for brokers, plan sponsors, education and enforcing Group Benefits administrative rules and guidelines across our service model. There would also be occasional special handling with members to resolve escalated issues. This role is designed to provide seamless, ongoing post-sale support that enhances client satisfaction, streamlines issue resolution, and strengthens trusting relationships between brokers and Wawanesa Life. By acting as a single, knowledgeable resource, you will ensure comprehensive and efficient communication between external stakeholders, underwriters, and internal departments across the Group Benefits organization.

Job Responsibilities

Serve as the main liaison for brokers, plan sponsors, and occasionally members after the sale of a policy, overseeing and managing the administration of specific client Group Benefit plans according to established rules and guidelines, ensuring seamless and ongoing communication.

Provide comprehensive support to the sales team through all post-sale activities, including assistance with policy amendments and renewals.

Identifies process and documentation needs, assisting in their development and maintaining internal process manuals, decision documentation and administrative documents for plan administrators and business partners.

Building and maintaining strong client relationships through excellent service and Group Benefits expertise.

Review renewals, providing additional information to advisors where appropriate, supporting the negotiation to retain business.

Assist with generating detailed reports and analyzing data for internal and external stakeholders, supporting performance monitoring and informed decision-making.

Act as the central coordination point between external contacts and internal teams (such as underwriters, claims, and administration), ensuring that information is promptly and accurately transferred.

Coordinate and manage inquiries, issues or escalations by promptly assessing their urgency and ensuring that critical concerns are routed to the appropriate internal teams. This responsibility involves monitoring incoming client matters, determining priority based on impact and deadlines, and facilitating timely resolution while maintaining clear and consistent communication with stakeholders.

Collaborate closely with Regional Group Managers (RGMs) to streamline communication and support efficient post-sale processes.

Qualifications

Post-secondary education in a related field.

Minimum of 5+ years’ experience in a service or support role related to group benefits, insurance, or account management.

In-depth understanding of Group insurance principles and benefit plans, including health, dental, Life and disability insurance.

Maintain a high level of knowledge of product offerings, contracts and administrative policies and practices.

Excellent communication and interpersonal skills, with the ability to communicate at the right level for the intended audience, including internal and external customers.

Demonstrates strong attention to detail, with the ability to identify key information, solve problems effectively, make sound decisions, and manage time and tasks efficiently.

Ability to work independently and in a team environment.

Candidates must be willing and able to travel throughout their assigned region and across multiple provinces, including occasional overnight stays, as required.

Bilingualism is an asset.

Strong Microsoft Office skills are required.

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 View email address on ca.workus.org .

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.