Director, Commercial Insurance Business Planning & Performance

Employment Type: New Role

Working Business Language: English. This role is a head‑office position and requires communication with internal and external stakeholders across Canada. The successful candidate must be fully proficient in English.

Salary: The salary offered for this role is estimated to be within the range $160,000 – $200,000. Candidates with salary expectations outside this range are still encouraged to apply. Salary is one component of a holistic offering that includes annual bonus, leave of absence top‑up, generous vacation, personal days, premium‑free benefits and pension plan.

About Us: At Wawanesa Mutual Insurance Company we offer a hybrid work environment with flexibility to balance office (2 days per week or 15 hours per week in office) and remote work. You may work from Winnipeg, Vancouver, Calgary, Edmonton, Toronto (North York), Kitchener or Ottawa. Founded in 1896, we are one of Canada’s largest mutual insurers, serving over 1.7 million members and employing more than 3,300 people.

The Director, Commercial Insurance Business Planning & Performance coordinates business strategy development, provides trusted advice, insights and performance management across Commercial lines, partners and broker stakeholders. This role supports the SVP & Chief Commercial Lines Officer by monitoring market developments, gathering performance metrics and business insights, and enabling informed decision‑making. With leadership of business planning and market monitoring teams, the role builds a performance‑focused, member‑centric culture and balances high‑level strategy with tactical execution to achieve commercial line goals.

• Serve as an advisor to the Chief Commercial Lines Officer, delivering confidential counsel and perspective on priorities.
• Coordinate the Commercial Lines strategic and tactical business planning process, gathering relevant reporting and monitoring inputs and ensuring alignment with enterprise planning.
• Collaborate closely with executive leadership to translate strategic objectives into measurable initiatives and performance indicators.
• Oversee the design and execution of executive reporting dashboards, business reviews and decision‑support analytics for the SVP and senior leadership.
• Monitor and analyze external competitor and market developments, industry benchmarks and risk to present actionable information and prepare the organization for change.
• Foster a collaborative environment that brings together sales operations, finance, compliance, legal and strategy to address performance and planning needs holistically.
• Create and manage agendas and execute logistics for Commercial Lines senior leadership meetings, communication forums (e.g., Townhalls, Ask Anything sessions) and track follow‑ups.

• Bachelor’s degree in business, insurance, actuarial science, analytics or a related field; MBA or equivalent advanced education is an asset.
• Minimum 8–10 years of experience in strategic or business planning, performance reporting in the insurance industry.
• Proven leadership experience managing cross‑functional teams and delivering results in a matrixed environment.
• Strong understanding of insurance operations and industry financial and non‑financial performance drivers.
• Demonstrated ability to translate strategy into action, drive execution and measure impact through structured performance frameworks.
• Excellent analytical, problem‑solving and organizational skills with comfort working with data, financials and reporting tools.
• Exceptional versatility, agility, situational awareness and composure; proven ability to handle multiple issues and prioritize critical work.
• Effective communicator and collaborator with strong presentation skills and ability to influence senior stakeholders.
• Deep alignment with Wawanesa’s values and purpose, passionate about supporting members and improving the way we work.
• Willingness to travel across regions and business units as needed.
• Agile business mindset focused on innovative problem‑solving and interdepartmental collaboration.

Wawanesa is committed to Diversity, Equity, Inclusion, and…