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Wawanesa Insurance

Manager, Underwriting Enablement - Commercial Lines

Toronto, ON, Canada
North York - Toronto, ON (Hybr, ON, Canada

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Job details

Working hours: 15 hours per week
Posting language: English
Posted: Oct 1, 2026

Original job description

Job ID: 10336

Employment Type: New 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: Toronto (North York), ON

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: $130,000 - $155,000. 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, 100% owned by its members, with more than $4.1 billion in annual revenue and $12.5 billion in assets. Headquartered in Winnipeg, Wawanesa is the parent company of Wawanesa Life, which provides life insurance solutions throughout Canada, and Western Financial Group, a leading national distributor of personal and business insurance. In March of 2026, Wawanesa entered into an agreement to acquire Everest Insurance Company of Canada to strengthen its commercial insurance capabilities and advance its long-term growth strategy.

Wawanesa proudly serves more than 1.8 million members and we are home to more than 3,000 employees across Canada. The company actively gives back to organizations that strengthen communities, donating more than $4 million annually to charitable organizations, including more than $2 million each year in support of people on the front lines of climate change. Learn more at 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 Manager, Underwriting Enablement – Commercial Lines is responsible for leading national initiatives that align with enterprise priorities and elevate underwriting operations by bringing together deep underwriting expertise, technology integration, learning and capability development, and execution of modernization initiatives. The Manager will lead a high-performing team focused on identifying opportunities, connecting appropriate stakeholders, and translating business needs into practical solutions that ensures an integrated approach to talent, learning, knowledge, tools, and technology.

Job Responsibilities

Lead the execution of national initiatives that align with enterprise priorities and enhance underwriting operations.
Monitor initiative performance, including improvements in efficiency, accuracy and speed achieved through technology, automation, and digital capabilities.
Drive the adoption of improved tools, processes, insights, AI, automation, and digital capabilities that enhance the underwriting experience, data-driven decision making and support Commercial Lines modernization objectives.
Serve as a trusted strategic partner to underwriting and operational leaders by identifying opportunities to strengthen underwriting effectiveness and support business priorities.
Support Commercial Lines underwriting effectiveness by translating appetite, governance, workflow, and best-practice expectations into practical tools, training, coaching, and process improvements that strengthen consistency, capability, and adoption across underwriting teams.
Translate business needs into practical solutions by connecting the appropriate resources, coordinating across stakeholders, and supporting effective implementation of initiatives.
Lead a team that builds sustainable underwriting capability through targeted learning, communications, coaching, curriculum development, knowledge management, and resources that simplify complex topics.
Drive greater consistency in underwriting practices, decision-making, and application of appetite across Commercial Lines.
Foster a culture of continuous learning and professional development across the underwriting community.
Leverage operational and underwriting insights to identify trends, opportunities, and areas for improvement in tools, processes, knowledge, and capability.
Coordinate with Learning & Development, Technology, operational leaders, and other supporting teams to ensure an integrated approach to underwriting talent, learning, knowledge, tools, and technology.

Qualifications

Minimum 10 years of experience in property and casualty underwriting, with at least 3 years in leadership capacity preferred.
Post-secondary degree (completed CIP and CRM or equivalent Property and Casualty Industry Designation considered an asset).
Proven leadership ability to influence, build trust, and lead cross-functional teams without direct authority, combined with strong negotiation skills to gain alignment.
Strong background in process improvement, operational excellence and workflow design.
Exceptional interpersonal, communication and stakeholder engagement skills, with the ability to translate technical concepts for varied audiences.
Advances business acumen with demonstrated analytics, problem-solving, and strategic execution capabilities.
Excellent organization and time management skills, with the ability to manage multiple priorities in a fast-paced environment.
Proficiency in Microsoft Office Suite (Excel, PowerPoint, Word); familiarity with data visualization tools (e.g., Power BI) is an asset.
Willingness and ability to travel.

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 jobs@wawanesa.com.

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.

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More about this job

Responsibilities

Lead national initiatives that modernize Commercial Lines underwriting operations, improve efficiency and consistency, and promote adoption of technology, automation, AI, and digital capabilities. Manage a team that develops underwriting tools, learning, coaching, communications, and knowledge resources while partnering with business, technology, and learning stakeholders to implement practical improvements.

Requirements

Requires at least 10 years of property and casualty underwriting experience; leadership experience of at least three years is preferred. A post-secondary degree is required, while completed CIP and CRM or an equivalent property and casualty industry designation is an asset; strong leadership, process improvement, communication, analytical, organizational, and Microsoft Office skills are also sought.

Skills

Commercial Lines Underwriting
Leadership
Cross-Functional Collaboration
Stakeholder Engagement
Process Improvement
Operational Excellence
Workflow Design
Strategic Execution
Business Acumen
Analytics
Problem-Solving
Negotiation
Learning And Development
Knowledge Management
Change Adoption
Microsoft Office

Benefits

Annual Bonus Plan
Leave Of Absence Top-Up Programs
Vacation Time
Personal Days
Premium-Free Benefits
Pension Plan

Visa sponsorship

Not detected in the job text

Keywords

Property And Casualty Insurance
Commercial Lines
Underwriting
Underwriting Enablement
Underwriting Appetite
Underwriting Governance
Workflow Design
Process Improvement
Operational Excellence
Underwriting Modernization
Artificial Intelligence
Automation
Digital Capabilities
Data-Driven Decision-Making
Learning And Development
Curriculum Development
Coaching
Knowledge Management
Stakeholder Engagement
Cross-Functional Leadership
Performance Monitoring
Microsoft Excel
Microsoft PowerPoint
Microsoft Word
Power BI
CIP
CRM

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