Manager, Underwriting Enablement - Commercial Lines

Wawanesa; Toronto; Hybrid; CAD 130,000 - 155,000; Full time

Benefits offered by this job

Annual bonus plan

Leave of absence top-up

Generous vacation time

Personal days

Premium free benefits

Pension plan

Job summary

The Manager, Underwriting Enablement – Commercial Lines at The Wawanesa Mutual Insurance Company leads national initiatives to modernize underwriting capabilities. The role combines strong underwriting expertise with technology, learning, and capability development to deliver integrated solutions across talent, knowledge, tools and processes.

You will manage a high-performing team, drive adoption of new tools and processes, and partner with leaders across underwriting and operations to improve

Qualifications

• Minimum 10 years of experience in property and casualty underwriting, with at least 3 years in leadership.
• Post-secondary degree; 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.
• Strong background in process improvement, operational excellence and workflow design.
• Exceptional interpersonal, communication and stakeholder engagement skills.
• Analytical mindset with strategic execution capabilities.
• Excellent organization and time management skills; ability to manage multiple priorities.
• Proficiency in MS Office; familiarity with Power BI is an asset.
• Willingness and ability to travel.

Responsibilities

• Lead national initiatives that align with enterprise priorities and enhance underwriting operations.
• Monitor initiative performance, including efficiency gains through technology, automation, and digital capabilities.
• Drive adoption of improved tools, processes, insights, AI, automation, and digital capabilities for underwriting modernization.
• Serve as a trusted strategic partner to underwriting and operational leaders.
• Translate appetite, governance, workflow, and best-practice expectations into practical tools, training and processes.
• Coordinate resources across stakeholders to implement initiatives effectively.
• Lead a team delivering learning, communications, coaching, curriculum development, and knowledge management.
• Foster consistency in underwriting practices and decision-making across Commercial Lines.
• Promote continuous learning and professional development across the underwriting community.
• Leverage insights to identify trends and opportunities to improve tools, processes, and capability.
• Coordinate with Learning & Development, Technology and operations to ensure integrated talent, knowledge, tools, and technology.

Skills

Leadership

Stakeholder engagement

Analytics

Project management

Change management

Communication

Time management

Travel willingness

Problem solving

Education

Post-secondary degree

CIP and CRM or equivalent asset

Tools

Microsoft Office

Power BI

Job description

Location: North York - Toronto, ON (Hybr, CA

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.

• annual bonus plan


• leave of absence top-up programs


• generous vacation time


• personal days


• premium free benefits


• 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 [e-mail] .

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.