Director, Personal Lines, Business Planning & Performance

Wawanesa Insurance; Toronto; Hybrid; CAD 120,000 - 140,000; Full time

Benefits offered by this job

Annual bonus plan

Leave top-up

Generous vacation time

Personal days

Premium-free benefits

Pension plan

Job summary

The Wawanesa Mutual Insurance Company is seeking a Director, Personal Lines, Business Planning & Performance to coordinate strategy and performance across Personal Lines. You will provide trusted advice to the SVP and build dashboards and reports for executive leadership.

You will lead cross‑functional teams, monitor market developments, and translate strategy into measurable initiatives while aligning planning and execution with enterprise priorities.

Qualifications

• Bachelor’s degree in business, insurance, actuarial science, analytics, or related field.
• MBA or equivalent advanced education is an asset.
• 8–10 years in strategic or business planning, performance reporting, or leadership in the P&C insurance industry.
• Proven leadership delivering results in a matrixed environment.
• Strong understanding of insurance operations and risk management.

Responsibilities

• Serve as advisor to the Chief Personal Lines Officer on planning and performance.
• Coordinate Personal Lines strategic and tactical planning.
• Translate objectives into measurable initiatives and dashboards for executives.
• Monitor external market developments and provide actionable insights.
• Foster collaboration across sales, operations, finance, compliance, legal, and strategy.
• Drive cross-functional initiatives and deliver results through influence.
• Prepare agendas and logistics for Senior Leadership meetings and town halls.

Skills

Leadership

Cross-functional

Strategic thinking

Analytics

Communication

Presentation

Education

Bachelor’s degree in business/insurance/analytics

MBA or equivalent

Job description

Job ID: 10365
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; Calgary, AB; oronto (North York), ON; Kitchener.
Working Business Language: 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: $120,000 - $140,000. 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, 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. Learn more at wawanesa.com.
We are currently seeking dedicated, driven, and enthusiastic individuals who thrive in a dynamic environment, embrace change, and are eager to gain diverse experience while advancing their careers as part of a growing team.

Job Overview

The Director, Personal Lines, Business Planning & Performance is responsible for coordinating business strategy and planning development, providing trusted advice, insights and performance management across the Personal lines of business and key business partners.
This role provides critical support to the SVP & Chief Personal 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. This role also brings together pertinent information (performance metrics, business insights and market data) into a cohesive view and narrative for the Line of Business for Executive and Board reporting. With direct leadership of cross functional business planning and market monitoring, 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 in the coming years.

Job 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 across the line of business.


• Coordinate the Personal 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.


• Drive cross-functional initiatives and deliver results by executing through influence, effectively navigating a matrixed structure without direct authority.


• Create and manage agendas and execute logistics for Personal Lines Senior Leadership meetings (including strategy and offsite sessions), Personal 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, 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, including analyzing complex issues from multiple angles and provide sound counsel among competing priorities.


• 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, including experience in financial literacy and quantitative analysis, with the ability to distill actionable insights.


• Effective communicator and collaborator, with strong storytelling and 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.


• Flexibility to travel within Canada and work variable hours, including overtime, as required.


• Agile business mindset with a focus on innovative problem-solving and interdepartmental collaboration.


• Exceptional written and verbal communication skills, including executive-level correspondence.

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 [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.