Manager, Underwriting Enablement in Toronto

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.

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.

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.

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.