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About the Role
The Manager, Underwriting Enablement – Commercial Lines leads national initiatives to enhance underwriting operations by integrating expertise, technology, learning, and modernization. This role focuses on identifying opportunities, connecting stakeholders, and translating business needs into practical solutions for talent, learning, knowledge, tools, and technology.
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.
Requirements
- Minimum 10 years of experience in property and casualty underwriting.
- At least 3 years in a leadership capacity preferred.
- Proven leadership ability to influence, build trust, and lead cross-functional teams without direct authority.
- Strong negotiation skills to gain alignment.
- Strong background in process improvement, operational excellence and workflow design.
- Exceptional interpersonal, communication and stakeholder engagement skills.
- Ability to translate technical concepts for varied audiences.
- Advanced business acumen with demonstrated analytics, problem-solving, and strategic execution capabilities.
- Excellent organization and time management skills.
- Ability to manage multiple priorities in a fast-paced environment.
- Willingness and ability to travel.
Skills
- Microsoft Office Suite (Excel, PowerPoint, Word)
- Data visualization tools (e.g., Power BI) is an asset
Location
- Toronto (North York), ON
Work Type
- Hybrid
- Remote
- Onsite
Experience Level
- 10+ years of experience in property and casualty underwriting
- 3+ years in leadership capacity preferred
Education Level
- Post-secondary degree
- CIP and CRM or equivalent Property and Casualty Industry Designation considered an asset
Salary/Compensations
- $130,000 - $155,000
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, 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 is 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.
- 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.
Equal Opportunity
- 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.