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About the Role

The Director, Personal Lines, Business Planning & Performance is responsible for coordinating business strategy and planning development, providing trusted advice, insights, and performance management across Personal Lines of business and key business partners. This role supports the SVP & Chief Personal Lines Officer by monitoring market developments and gathering performance metrics to enable informed decision-making and identify opportunities for improvement.

Responsibilities

Serve as an advisor to the Chief Personal Lines Officer, delivering confidential counsel and perspective on matters of priority to Personal Lines planning and performance.
Coordinate the Personal Lines strategic and tactical business planning process, ensuring alignment with enterprise planning processes and priorities.
Collaborate 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.
Monitor and analyze external competitor and market developments, industry benchmarks, and risk to present actionable information.
Foster a collaborative environment to address performance and planning needs holistically.
Drive cross-functional initiatives and deliver results by executing through influence in a matrixed structure.
Create and manage agendas and execute logistics for Personal Lines Senior Leadership meetings and communication forums.
Track follow-ups for leadership meetings and forums.

Requirements

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, operational leadership, or regulatory compliance in the P&C insurance industry.
Proven leadership experience managing cross-functional teams and delivering results in a matrixed environment.
Strong understanding of insurance operations, risk management, 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.
Ability to analyze complex issues from multiple angles and provide sound counsel among competing priorities.
Experience in financial literacy and quantitative analysis, with the ability to distill actionable insights.
Exceptional written and verbal communication skills, including executive-level correspondence.
Flexibility to travel within Canada and work variable hours, including overtime, as required.

Skills

Analytical skills
Problem-solving skills
Organizational skills
Working with data, financials, and reporting tools
Versatility
Agility
Situational awareness
Composure
Prioritization
Storytelling skills
Presentation skills
Influencing senior stakeholders
Agile business mindset
Innovative problem-solving
Interdepartmental collaboration

Location

Winnipeg, MB
Calgary, AB
Toronto (North York), ON
Kitchener

Work Type

Hybrid work environment
Full-time
Part-time

Experience Level

8-10 years of experience
Leadership experience

Education Level

Bachelor’s degree in business, insurance, actuarial science, analytics, or a related field
MBA or equivalent advanced education is an asset

Salary/Compensations

$120,000 - $140,000

Benefits

Annual bonus plan
Leave of absence top-up programs
Generous vacation time
Personal days
Premium free benefits
Pension plan

About the 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.

Equal Opportunity

Wawanesa is committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believes 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.
All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.
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.