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Job ID: 9600

Employment Type: New Role

Working Business Language: English; this role is considered a head‑office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is 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 are provided with generous vacation time, personal days, premium free benefits and a pension plan. The salary offered for this role is estimated to be within the $100,000–$130,000 range. Candidates with salary expectations outside of the range are still encouraged to apply.

About Us

At Wawanesa, 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: Winnipeg, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth, NS.

The Wawanesa Mutual Insurance Company ("Wawanesa Mutual") was founded in 1896 and is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Its National Headquarters is in Winnipeg, and it is the parent company of Wawanesa Life and Western Financial Group. Wawanesa serves more than 1.7 million members in Canada and employs over 3,300 people across the country. We give back to communities, donating more than $3.5 million annually to charitable organizations and supporting front‑line climate change efforts. We are proud to be recognized as one of Manitoba’s Top Employers. For more information, visit wawanesa.com.

We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and want diverse experience and advancement on a growing team.

The Underwriting Enablement Program Manager – Personal Lines is responsible for driving national initiatives that align with enterprise priorities and elevate underwriting operations through automation and technology integration. This role focuses on advancing digital transformation, streamlining workflows, and enhancing operational efficiency by reducing manual effort and optimizing processes. The position requires strong expertise in underwriting operations, process improvement, and technology adoption to deliver impactful solutions across the organization.

• Execute national initiatives that align with enterprise priorities and improve underwriting operations. Monitor initiative performance, measuring efficiency, accuracy, and speed improvements achieved through automation and digital enablement.
• Drive adoption of AI and automation technologies to optimize underwriting workflows and support data‑driven decision‑making.
• Partner with technology teams to identify, test, and implement digital tools that enhance productivity and performance.
• Analyze workflow challenges and recommend process improvements to simplify operations, reduce manual effort, and increase efficiency.
• Champion digital transformation by fostering awareness, understanding, and readiness across underwriting operations.
• Manage governance of Straight Through Processing (STP), including issue intake, tracking, resolution, and continuous workflow optimization.
• Support rollout of new products and pricing strategies by embedding underwriting best practices and ensuring operational readiness.
• Develop engaging educational materials and training programs that build AI literacy, technical fluency, and confidence in digital workflows. Create and deliver communications and resources that simplify complex topics and promote consistent adoption of underwriting standards and new processes.

• Minimum 10 years of experience in property and casualty underwriting; experience in leading initiatives or influencing change strongly preferred.
• Post‑secondary degree (CIP and CRM or equivalent Property and Casualty Industry Designation considered an asset).
• Demonstrated ability to influence and build trust across cross‑functional teams without direct authority; strong negotiation skills to gain alignment.
• Proven expertise in process improvement, operational excellence, and workflow design.
• Exceptional interpersonal and communication skills, with the ability to translate technical concepts for varied audiences.
• Advanced business acumen with strong analytical, 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.

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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 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 hiring leaders in compliance with all applicable legislation.