Director, Commercial Lines - Property

Wawanesa Insurance; Toronto; Hybrid; CAD 180,000 - 210,000; Full time

Job summary

A leading Canadian insurance provider is seeking a Director, Commercial Lines Property Insurance in Toronto. The role requires 10+ years of commercial property insurance experience, including 5 years in leadership. Responsibilities include developing underwriting strategy, monitoring market trends, and managing broker relationships. The ideal candidate will have strong analytical and communication skills, and a Bachelor's degree. The position offers a hybrid work environment with a competitive salary of CAD 180,000 - 210,000.

Benefits

Annual bonus

Generous vacation time

Premium free benefits

Pension plan

Qualifications

• 10+ years experience in commercial property insurance.
• 5+ years in a leadership role.
• Deep knowledge of Canadian insurance markets.

Responsibilities

• Lead underwriting strategy for commercial property lines.
• Monitor market trends and inform pricing decisions.
• Manage relationships with brokers and reinsurers.

Skills

Leadership

Analytical skills

Communication

Relationship-building

Strategic planning

Education

Bachelor’s degree in Business or related field

CIP, FCIP, CRM designations

Job description

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: $180,000 - $210,000. 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; Montreal, QC; Quebec City, QC; Moncton, NB; Dartmouth, NS.

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.

Opportunity

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 Lines Property Insurance, is a strategic leader responsible for driving underwriting excellence, portfolio performance, and product innovation in commercial property insurance. This role partners closely with the VP, Commercial Insurance—Products & Pricing to ensure alignment with Wawanesa’s purpose, values, and business objectives, while fostering a culture of integrity, collaboration, and continuous improvement.

Responsibilities

• Lead the development and execution of underwriting strategy, appetite, and governance for commercial property lines, ensuring decisions reflect Wawanesa’s commitment to prudent risk management and sustainable growth.
• Monitor market trends, loss ratios, leading indicators and emerging risks to inform pricing and product decisions that support our members and communities.
• Champion initiatives to enhance profitability, retention, and growth, collaborating with product, actuarial, and claims teams to deliver innovative solutions.
• Manage third‑party relationships, including reinsurance for mechanical breakdown, ensuring performance and exploring new opportunities to strengthen our offerings.
• Oversee accumulation management strategies, including CAT perils, to safeguard Wawanesa’s financial strength.
• Mentor and develop a high‑performing team of technical underwriting specialists, fostering accountability, professional growth, and a member‑first mindset.
• Develop and maintain underwriting guidelines, policy wordings, and risk selection criteria.
• Provide technical guidance and referral support for complex or high exposure accounts.
• Ensure underwriting practices comply with internal standards, reinsurance contracts and regulatory requirements.
• Identify opportunities for continuous improvements to underwriting systems, workflows, and processes.
• Oversee underwriting audits and ensure adherence to quality assurance standards.
• Support enterprise risk management and strategic planning initiatives.
• Build and maintain strong relationships with brokers, reinsurers, industry associations and internal departments (e.g., Claims, Risk Services, Actuarial).
• Work with Commercial operational VPs to ensure alignment and profitability within these segments. Act as a trusted advisor on relevant transformation initiatives.
• Represent the company in industry forums and conferences to reinforce thought leadership.
• Support business development efforts through strategic broker engagement and account planning.

Qualifications

• Minimum 10+ years of experience in commercial property insurance, with at least 5 years in a leadership role or head office experience.
• Bachelor’s degree in Business, Risk Management, or related field; advanced degrees or designations (CIP, FCIP, CRM) preferred.
• Deep knowledge of Canadian commercial insurance markets, regulatory frameworks, and distribution channels.
• Proven ability to lead teams, manage complex portfolios, and deliver profitable growth.
• Strong analytical, strategic planning, and decision‑making skills.
• Excellent communication, negotiation, and relationship‑building abilities.

Preferred Attributes

• Experience with underwriting automation and digital transformation initiatives.
• Familiarity with environmental and specialty property risks.
• Ability to interact with executive leadership and influence strategic direction.

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 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.