Date: Jul 9, 2026
Location: North York - Toronto, ON (Hybr, CA Ottawa, ON (Hybrid), CA Calgary, AB (Hybrid), CA Winnipeg, MB (Hybrid), CA Kitchener, ON (Hybrid), CA Dartmouth, NS (Hybrid), CA Vancouver, BC (Hybrid), CA Montreal, QC (Hybrid), CA Edmonton, AB (Hybrid), CA Moncton, NB (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 10173
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; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, 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: $90,000 - $110,000. 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
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.
Job Responsibilities
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.
Qualifications
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).
Working knowledge of Canadian P&C insurance dynamics, including awareness of regulatory bodies (e.g., FSRA, CCIR) and their impact on product design.
CIP designation or progress toward completion is an asset.
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.
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
[email protected] .
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.
