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Wawanesa Insurance

Manager, Application Delivery

Toronto, ON, Canada
AB, Canada
Winnipeg, MB, Canada
Kitchener, ON, Canada
Vancouver, BC, Canada
Calgary, AB, Canada
North York - Toronto, ON (Hybr, ON, Canada
Edmonton, AB (Hybrid), AB, Canada

Experience: 5 years’ experience in a senior IS role.
Working hours: 15 hours per week
Posting language: English
Posted: Sep 29, 2026

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Original job description

Job ID: 10372

Employment Type: Existing Role

Work Environment: 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.

Working Business Language: 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 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 - $180,000. Candidates with salary expectations outside of the range are still encouraged to apply.

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.

Wawanesa proudly serves more than 1.8 million members and we are 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. Learn more at wawanesa.com.

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.

Job Overview

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 strong relationships with business stakeholders across pricing, product, and both broker and member experience, aligning delivery with business priorities while balancing speed, quality, and compliance.

Job Responsibilities

Maintain accountability for the establishment of development and delivery plans with all the required stakeholders.
Manage resources to ensure successful completion of work assignments.
Communicate plans, progress and deliverables to all required stakeholders.
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.
Oversee and coach a team to ensure work environment is respectful, challenging, and rewarding and employees are maximized to their full potential while contributing to the achievement of the company's goals.
Contribute to budget preparation and management to budget as forecasted.
Perform other duties as assigned.

Qualifications

5 years’ experience in a senior IS role.
Post-secondary degree/certificate or equivalent experience.
Completion of, or working towards, a recognized management certification.
Experience with relevant methodologies and technologies.
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.
Strong Leadership skills with the ability to build, develop, lead, and support a diverse team.
Ability to develop effective plans that define activities, resources, timelines and cost estimates.
Ability to make well justified decisions in complex and high pressure situations.
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.

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.

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More about this job

Responsibilities

This role leads application delivery for Commercial Lines and Claims, overseeing the maintenance and enhancement of systems including AI and Guidewire solutions. The manager is responsible for coaching a multi-layered team and building strong relationships with business stakeholders to align delivery with organizational priorities.

Requirements

Candidates must have at least 5 years of experience in a senior IS role and possess a post-secondary degree or equivalent experience. Strong leadership, analytical, and communication skills are required, along with the ability to manage complex projects and budgets.

Skills

Application delivery
Team leadership
Project management
Stakeholder management
Strategic planning
Budget management
Coaching
Process improvement
Analytical skills
Problem solving
Commercial lines insurance
Claims systems
Guidewire
Artificial intelligence

Benefits

Annual bonus plan
Leave of absence top-up programs
Generous vacation time
Personal days
Premium free benefits
Pension plan

Visa sponsorship

Not detected in the job text

Keywords

Application Delivery
Commercial Lines
Claims
Guidewire
Artificial Intelligence
Software Development
System Maintenance
Project Management
Budgeting
Operational Planning
Stakeholder Management
Insurance
Finance
Leadership
Coaching
Process Improvement
Change Management
Compliance
Risk Management
Strategic Planning

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