Director, Commercial Insurance - Business Planning & Performance

Wawanesa Insurance; Toronto; Hybrid; CAD 160,000 - 200,000; Full time

Job summary

A leading mutual insurance company in Toronto is seeking a Director, Commercial Insurance to lead strategic planning and performance management initiatives in the insurance industry. This role will involve advising senior leadership, coordinating business strategies, and analyzing market developments. The ideal candidate will have 8-10 years' experience in strategic planning and proven leadership skills. Join a company committed to values of service and community support while working in a hybrid environment.

Benefits

Annual bonus plan

Generous vacation time

Pension plan

Flexible hybrid work environment

Qualifications

• 8–10 years of experience in strategic or business planning in the insurance industry.
• Proven leadership experience managing cross-functional teams.
• Strong understanding of insurance operations and performance drivers.

Responsibilities

• Coordinate strategic and tactical business planning processes.
• Collaborate with executive leadership on measurable initiatives.
• Monitor external market developments to support decision-making.

Skills

Strategic planning

Leadership

Analytical skills

Communication

Problem-solving

Education

Bachelor’s degree in business or related field

MBA or equivalent advanced education

Tools

Reporting tools

Job description

Job ID: 9641

Employment Type: New Role

Working Business Language: English. This role is considered a head‑office role and will be required to communicate with internal and external stakeholders across Canada where the primary business language for this role is English. As such, the successful candidate must be fully proficient in 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 are provided with generous vacation time, personal days, premium free benefits and a pension plan. The salary offered for this role is estimated to be within the following range: $160,000 – $200,000. Candidates with salary expectations outside of the range are still encouraged to apply.

About Us

At Wawanesa, 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.

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 3,300 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. We are also proud to be recognized as one of Manitoba’s Top Employers. 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.

Job Overview

The Director, Commercial Insurance – Business Planning & Performance is responsible for coordinating business strategy development, providing trusted advice, insights and performance management across the Commercial lines of business, business partners and broker stakeholders. This role provides critical support to the SVP & Chief Commercial Lines Officer by monitoring market developments and gathering internal and external performance metrics and business insights to enable informed decision‑making, identifying opportunities for improvement, and ensuring enterprise‑level alignment in planning, reporting, and execution.

With direct leadership of business planning and market monitoring teams, this role is instrumental in building a performance‑focused and member‑centric culture. This role requires balancing high‑level strategic work with tactical execution, ensuring focus on achieving Wawanesa’s critical goals for Commercial Lines in the coming years.

In all responsibilities, this leader champions Wawanesa’s purpose. Helping communities thrive in a changing world is modeled through our values of Service, Respect, Performance, Teamwork and Openness ensuring they are reflected in planning, performance measurement, and regulatory accountability.

Responsibilities

• Serve as an advisor to the Chief Commercial Lines Officer, delivering confidential counsel and perspective on matters of priority to Commercial Lines planning and performance.
• Coordinate the Commercial Lines strategic and tactical business planning process, gathering the relevant operational reporting / performance monitoring inputs, ensuring alignment with enterprise planning processes and priorities.
• 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 to support decision‑making and prepare the organization to adapt effectively and proactively to changes.
• 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 (including strategy and off‑site sessions), Commercial Lines communication forums (e.g., Townhalls, Ask Anything sessions, etc.) and track follow‑ups.

Qualifications

• 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 well‑structured performance frameworks.
• Excellent analytical, problem‑solving, and organizational skills, with a high degree of comfort working with data, financials, and reporting tools.
• Exceptional versatility, agility, situational awareness, and composure. Proven ability to navigate multiple issues concurrently and prioritize critical work.
• Demonstrated ability to analyze complex issues from multiple angles and provide sound counsel among competing priorities.
• Effective communicator and collaborator, with strong presentation skills and the ability to influence senior stakeholders.
• Deep alignment with Wawanesa’s values and purpose, with a passion for supporting people, protecting members, and improving the way we work.
• Willingness to travel as needed across regions and business units.
• Agile business mindset with a focus on innovative problem‑solving and interdepartmental collaboration.

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 racialised 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].

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.