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. Toronto (North York), ONWorking Business Language: English.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.

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.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.

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. 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.Post-secondary degree (completed CIP and CRM or equivalent Property and Casualty Industry Designation considered an asset).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.Excellent organization and time management skills, with the ability to manage multiple priorities in a fast-paced setting.Proficiency in Microsoft Office Suite (Excel, PowerPoint, Word); familiarity with data visualization tools (e.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.If you require accommodations during any stage of the recruitment process, please reach out in confidence to [email protected] Wawanesa job applicants are subject to Wawanesa's Privacy Policy.

📌 Manager, Underwriting Enablement - Commercial Lines (Winnipeg)
🏢 Wawanesa Insurance
📍 Winnipeg