Product Owner, Direct Venture

Wawanesa; Winnipeg; Hybrid; CAD 95,000 - 135,000; Full time

Benefits offered by this job

Annual bonus

Leave top-up program

Generous vacation time

Personal days

Pension plan

Job summary

The Wawanesa Mutual Insurance Company is seeking a Product Owner to lead the success, strategy, and evolution of an assigned insurance product within its Direct-to-Member business. You will act as the primary business owner and SME, driving roadmaps, member experience, performance, and delivery outcomes in a venture-style environment.

You will partner with Business Analysts, technology, pricing, underwriting, claims, operations, and other stakeholders to keep products competitive, compliant, and

Qualifications

• 5+ years of product management or ownership experience in insurance; Property & Casualty preferred.
• Experience leading product initiatives from concept through implementation in Agile environments.
• Experience evaluating product performance and using data to make decisions; digital or direct-to-consumer delivery is an asset.

Responsibilities

• Develop and communicate product strategies, roadmaps, and priorities that translate business objectives into actionable delivery plans.
• Identify and prioritize enhancements that improve member experience, conversion, growth, retention, and efficiency.
• Partner with Business Analysts to translate priorities into user stories, requirements, and acceptance criteria, and guide delivery teams throughout development.
• Make trade-off decisions balancing member experience, business value, timelines, and risk.
• Establish, monitor, and report product KPIs and OKRs.
• Own and improve the end-to-end digital member journey, including quote, purchase, self-service, and retention, using research and test-and-learn experimentation.
• Serve as product subject matter expert across coverages, underwriting guidelines, processes, and member journeys, ensuring delivered solutions reflect product intent.
• Maintain product documentation, requirements, and reference materials.
• Ensure compliance with legal, regulatory, and governance requirements; assess legislative and industry changes and support risk, audit, quality, and control activities.
• Build partnerships across Pricing, Underwriting, Claims, Operations, Customer Experience, Marketing, Analytics, Compliance, and Technology to align objectives and priorities.
• Communicate product priorities, decisions, performance, risks, and opportunities to stakeholders and leaders.
• Promote member-centricity, accountability, innovation, and continuous improvement.
• Guide, coach, and provide escalation support to Associate Product Owners.
• Perform other duties as assigned.

Skills

Product strategy

Roadmap planning

Agile / Scrum

Stakeholder management

Data-driven decision making

Education

Post-secondary degree in a related discipline

CIP or equivalent Property & Casualty designation

Job description

Select how often (in days) to receive an alert:

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

Job ID:10407

Employment Type: New 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: $95,000 - $135,000 . 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

The Product Owner is accountable for the success, performance, and evolution of an assigned insurance product or capability within Wawanesa’s Direct-to-Member (D2M) business. As the primary business owner and subject matter expert, they lead product strategy, digital member experience, performance, roadmaps, priorities, and delivery outcomes.Working in a venture-style environment, the Product Owner combines strategic thinking, hands‑on delivery support, member discovery, and business decision‑making.

They partner with Business Analysts, technology, pricing, underwriting, claims, operations, customer experience, and other stakeholders to keep products competitive, compliant, effective, and aligned with D2M objectives. They own product priority, scope, and intent and make product decisions on behalf of the business.

Job Responsibilities

• Develop and communicate product strategies, roadmaps, and priorities that translate business objectives into actionable delivery plans.
• Identify and prioritize enhancements that improve member experience, conversion, growth, retention, and efficiency, informed by member insights, data, industry trends, regulation, and competition.
• Partner with Business Analysts to translate priorities into user stories, requirements, and acceptance criteria, and guide delivery teams throughout development.
• Make trade‑off decisions balancing member experience, business value, timelines, and risk.
• Establish, monitor, and report product KPIs and OKRs.
• Own and improve the end‑to‑end digital member journey, including quote, purchase, self‑service, and retention, using research and test‑and‑learn experimentation.
• Serve as product subject matter expert across coverages, underwriting guidelines, processes, and member journeys, ensuring delivered solutions reflect product intent.
• Maintain product documentation, requirements, and reference materials.
• Ensure compliance with legal, regulatory, and governance requirements; assess legislative and industry changes and support risk, audit, quality, and control activities.
• Build partnerships across Pricing, Underwriting, Claims, Operations, Customer Experience, Marketing, Analytics, Compliance, and Technology to align objectives and priorities.
• Communicate product priorities, decisions, performance, risks, and opportunities to stakeholders and leaders.
• Promote member‑centricity, accountability, innovation, and continuous improvement.
• Guide, coach, and provide escalation support to Associate Product Owners.
• Perform other duties as assigned.

Qualifications

• 5+ years of product management or ownership experience in insurance; Property & Casualty preferred.
• Experience leading product initiatives from concept through implementation in Agile environments.
• Experience evaluating product performance and using data to make decisions; digital or direct‑to‑consumer delivery is an asset.
• Post‑secondary degree in a related discipline and/or Chartered Insurance Professional (CIP) or equivalent Property & Casualty designation preferred.
• Strong knowledge of Property & Casualty products, coverages, underwriting principles, and operations.
• Strong analytical and problem‑solving skills, including sound decisions based on complex, incomplete, or evolving information.
• Experience developing product strategy, roadmaps, and priorities.
• Strong stakeholder management, communication, presentation, and facilitation skills.
• Strong planning, organization, and prioritization skills, balancing strategy with day‑to‑day execution.

#LI-AF1 #LI-Hybrid

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 [e-mail].

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.