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.

Working 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. Working under minimal direction,



this role contributes to Wawanesa’s success by ensuring the maintenance, support and enhancement of systems and applications. This role leads application delivery within Commercial Lines and Claims, providing AI and Guidewire solutions that benefit Wawanesa’s commercial property and auto lines of business as well as the Claims department.

This leader owns the implementation of enhancements, rate, and product changes, ensuring they are delivered accurately, on time, and with quality and efficiency across Canadian jurisdictions. The role manages a multi-layered team of developers and analysts, as well as delivery leaders who run their own delivery teams, and is accountable for coaching and growing that talent. A core part of the role is building and sustaining robust relationships with business stakeholders across pricing, product, and both broker and member experience, aligning delivery with business priorities while balancing speed, quality, and compliance.

Maintain accountability for the establishment of development and delivery plans with all the required stakeholders. Manage resources to ensure successful completion of work assignments. Ensure processes, methodologies, policies, and procedures are followed, and create or contribute to the creation of new processes, methodologies,



policies and procedures where appropriate.

Contribute to the building of, and execute against, the annual operational plan. Ensure continuous improvement in operational processes. Contribute to budget preparation and management to budget as forecasted. 5 years' experience in a senior IS role. ~ Completion of, or working towards, a recognized management certification. ~ Understanding of relevant analysis, design, system development and maintenance tools and techniques. ~ Ability to communicate, both verbally and in writing, in a persuasive and eloquent manner. ~ Advanced analytical and problem solving skills with the ability to manage and prioritize a busy workload and multiple projects. ~ Experience in the insurance/finance industry is considered an asset. #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] note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants.

📌 Manager, Application Delivery (Winnipeg)
🏢 Wawanesa
📍 Winnipeg