Associate Product Owner
Date: Oct 28, 2026
Location: Winnipeg, MB (Hybrid), CA Wawanesa, MB (Hybrid), CA North York - Toronto, ON (Hybr, CA Ottawa, ON (Hybrid), CA Edmonton, AB (Hybrid), CA Hybrid - Canada, CA Kitchener, ON (Hybrid), CA Vancouver, BC (Hybrid), CA Moncton, NB (Hybrid), CA Montreal, QC (Hybrid), CA Calgary, AB (Hybrid), CA Dartmouth, NS (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 10434
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: Winnipeg, MB; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Lethbridge, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Quebec City, QC, Moncton, NB; Dartmouth; NS.
Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is 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: $80,000 - $105,000. 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, fully owned by its more than 1.8 million members. Headquartered in Winnipeg, Wawanesa is the parent company of WSI™, a specialty insurer delivering tailored solutions built around unique needs; Wawanesa Life, a provider of life insurance products; and Western Financial Group, a leading national distributor of personal and commercial insurance.
Wawanesa is committed to helping communities thrive in a changing world. The company invests more than $4 million annually in charitable initiatives, including $2.5 million each year to support people and communities on the front lines of climate change. Learn more at wawanesa.com.
We are currently seeking dedicated, driven, and enthusiastic individuals who thrive in a dynamic environment, embrace change, and are eager to gain diverse experience while advancing their careers as part of a growing team.
Job Overview
As Associate Product Owner, you will play a key supporting role in the development and delivery of digital insurance solutions that align with strategic business goals and enhance member experience. Working closely with Product Owners and cross-functional teams, you will help translate high-level problem statements into actionable insights, maintain product backlogs, and ensure that system capabilities are fully understood and leveraged. This role is ideal for someone with strong analytical skills, a collaborative mindset, and a passion for continuous learning in the insurance technology space.
Job Responsibilities
- Shadow end users across business units to stay current on operational challenges, workflows, and member needs.
- Create and maintain content for bi-weekly and monthly product updates, ensuring clarity and alignment with strategic goals.
- Lead backlog grooming sessions and assist in prioritizing features and enhancements based on business value and member impact.
- Assist in the development of business cases and presentations that communicate product opportunities, risks, and benefits to stakeholders.
- Update and refine product metrics and requirements based on evolving problem statements and stakeholder feedback.
- Conduct thorough reviews of system capabilities to identify usage patterns, redundancies, and opportunities for optimization.
- Collaborate with Product Owners, developers, analysts, and business stakeholders to ensure alignment and transparency throughout the product lifecycle.
- Support roadmap planning by contributing insights on resource capacity, delivery timelines, and feature feasibility.
- Recommend enhancements and optimizations that improve member experience and operational efficiency.
- Track KPIs and assist in measuring benefits realized from product initiatives.
- Develop a strong understanding of insurance systems and processes to guide informed decision-making and support strategic outcomes.
- Other duties as assigned.
Qualifications
- 2+ years of experience in product support, business analysis, or operations within the insurance or financial services industry.
- Post-secondary education in Business, Technology, or a related field; insurance certifications (e.g., CIP) are an asset.
- Familiarity with Agile/Scrum methodologies and experience using tools like JIRA, Confluence, or similar platforms.
- Strong communication and documentation skills, with the ability to translate complex concepts into clear, actionable updates.
- Analytical mindset with a keen eye for identifying inefficiencies, redundancies, and improvement opportunities.
- Ability to work collaboratively across teams and build strong relationships with stakeholders.
- Experience supporting digital product development, especially in areas like underwriting, claims, or member engagement, is preferred.
Nice to Have:
- Experience in fraud prevention, regulatory compliance, or member retention strategies within insurance.
- Familiarity with omni-channel member experiences and digital transformation initiatives.
- Project management or Agile certifications (e.g., PMP, PMI-ACP).
- Background in data analytics or AI-driven product development.
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.