Remote Work jobs in Canada

Job ID: 9581

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: $90,000 - $120,000. Candidates with salary expectations outside of the range are still encouraged to apply.

At Wawanesa, we’re proud to 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; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; 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 3,600 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. 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.

The Product Innovation Strategist is responsible for identifying and validating future growth initiatives for Wawanesa’s Personal Lines business. This role explores emerging distribution models, including OEM, lender, digital, and data-driven partnerships. Evaluates new product concepts, designs pilot programs, and develops investment theses to support the product innovation pipeline. The position facilitates early-stage idea validation in collaboration with Strategy and Market Segment owners, and works cross-functionally with Pricing, Underwriting, Technology, Distribution, and Compliance to assess viability, measurability, and scalability. This role contributes to shaping the next generation of embedded, connected, and data-powered products.

• Opportunity Scouting: Identify and evaluate emerging innovation opportunities in connected insurance, embedded partnerships (OEMs, lenders, MGAs, digital platforms), and adjacent ecosystems (mobility, smart home, EV/ADAS).
• Strategic Fit & Economics: Assess potential partners and concepts for alignment to corporate strategy, financial viability, compliance posture, and data rights considerations.
• Business Case Development: Build investment theses and business cases for MVPs and pilot programs, including TAM sizing, expected LR/COR impact, operational complexity, and time-to-value.
• Pilot Design & Execution: Collaborate with Technology, Product Owners, and external partners to stand up proof-of-concepts and pilots; define success criteria, KPIs, and evaluation frameworks.
• Decision Support: Package findings into concise “go/no-go” recommendations for leadership, supported by evidence packs, financial models, and scenario analyses.
• Cross-Functional Integration: Partner closely with Pricing/Actuarial, Underwriting, Legal/Compliance, and Distribution to ensure new opportunities are executable within regulatory, pricing, and operational constraints.
• Market & Partner Intelligence: Maintain awareness of industry trends in embedded insurance, telematics, connected ecosystems, and digital distribution; benchmark against Canadian and global competitors.
• Storytelling & Influence: Translate complex analyses and pilot outcomes into clear, persuasive narratives that support decision-making at the executive and Board levels.

• 5+ years of experience in strategy, innovation, or business development within insurance, financial services, mobility, or technology sectors.
• Strong understanding of embedded distribution models, telematics, data ecosystems, and connected products (EV, IoT, ADAS).
• Demonstrated ability to develop business cases and translate conceptual opportunities into quantified recommendations.
• Excellent communication and storytelling skills; comfortable presenting to senior leadership.
• Proven ability to manage multiple concurrent projects and balance strategic and executional work.

Wawanesa is proud to be one of Manitoba’s Top Employers, a Kincentric Best Employer in Canada and a Forbes Best Employer in Canada recognizing an exceptional place to work!

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.

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