Manager, Application Delivery

Wawanesa; Winnipeg; Hybrid; CAD 130,000 - 180,000; Full time

Benefits offered by this job

Annual bonus plan

Leave of absence top-up

Generous vacation time

Premium-free benefits

Pension plan

Job summary

The Wawanesa Mutual Insurance Company is seeking a senior IS leader to deliver AI and Guidewire solutions across Commercial Lines and Claims. You will own enhancements, rate and product changes, ensuring timely, high-quality delivery while coaching a multi-layered delivery organization across Canada.

You will build strong relationships with pricing, product and broker/member stakeholders, balancing speed, quality and compliance in a hybrid work environment with offices across Canada.

Qualifications

• Five years of experience in a senior IS role.
• Post-secondary degree or equivalent required.
• Completion of, or working towards, a recognized management certification.
• Experience with relevant methodologies and technologies.
• Strong communication, both written and verbal, and persuasive skills.
• Advanced analytical and problem solving abilities with ability to manage multiple projects.
• Proven leadership to build, develop and lead a diverse team.
• Ability to plan activities, resources, timelines and costs.
• Experience in insurance/finance is an asset.

Responsibilities

• Establish development and delivery plans with stakeholders.
• Manage resources to complete work assignments.
• Communicate plans, progress and deliverables to stakeholders.
• Ensure processes and policies are followed and improve where appropriate.
• Contribute to the annual operational plan and budget.
• Drive continuous improvement of processes.
• Coach a team to maximize potential and align with company goals.
• Assist in budget preparation and forecasting.

Skills

Communication

Leadership

Analytical thinking

Budgeting

Stakeholder management

Strategic planning

Education

Post-secondary degree or equivalent

Management certification (in progress)

Tools

Guidewire

AI technologies

Job description

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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.

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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 [e-mail].

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.