Date: Jul 10, 2026
Location: North York - Toronto, ON (Hybr, CA Hybrid - Canada, CA Vancouver, BC (Hybrid), CA Edmonton, AB (Hybrid), CA Calgary, AB (Hybrid), CA Kitchener, ON (Hybrid), CA Ottawa, ON (Hybrid), CA Toronto, ON, CA, M2P-2B7 Winnipeg, MB (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 10176
Employment Type:
New 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; Ottawa, ON.
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 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 dat a, 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: $110,000 - $120,000. 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 supervision, the Senior Digital Transformation Specialist leverages insurance experience and strong analytical skills to translate business requirements into technology-enabled solutions aligned with Wawanesa's transformation vision and strategic priorities. This role is central to our ongoing efforts to modernize business processes, systems, and member experiences, acting as a bridge between business and technology teams to identify and implement digital transformation initiatives, automation opportunities, and AI-driven solutions. The role supports people readiness, adoption, and change management activities to help individuals and teams successfully navigate change. As a trusted advisor, the incumbent builds strong stakeholder relationships, drives process improvement, and enables business outcomes through the effective implementation of technology and digital solutions.
Job Responsibilties
Lead the evaluation and resolution of business requests using insurance expertise and knowledge of Wawanesa's systems to develop business requirements, develop and confirm business acceptance criteria, and optimize business process in alignment with Wawanesa's strategy, vision, and themes.
Lead requirements gathering sessions with stakeholders and document the results.
Lead the creation of test case acceptance criteria based on requirements documentation and defect resolutions.
Build and maintain trusted relationships with internal and external stakeholders, fostering collaboration and acting as a trusted advisor.
Lead cross-functional meetings and deliver presentations, including to executive audiences, to share insights, drive alignment, and establish work plans.
Apply system standards, strategic themes, and team methodologies while championing continuous improvement.
Coach, mentor and train team members including peer review of documentation.
Lead communication, engagement, training, and resistance management strategies, including training needs assessments and development of supporting materials.
Leads the development and use of performance metrics to define, measure and report on the progress and success of change and impacts to people on projects.
Act as a subject matter expert leading strategic initiatives, process optimization, reporting, product development, and broker, employee, and member experience improvements, including business case development.
Work with teams to maintain existing documentation so that it reflects up to date and accurate information.
Qualifications
Minimum five years' experience in property and casualty insurance or business analysis.
Completion of post-secondary degree/certificate or equivalent experience.
CIP/CPCU designation or actively working towards completion of designation.
Advanced analysis and conceptual thinking skills with the ability to conduct detailed analysis of information, and to select and implement best solutions.
Excellent communication, presentation and negotiation skills, with the ability to communicate in a clear and concise manner with style fitting for the audience and message.
Advance attention to detail skills to with the ability to develop relevant information, produce quality deliverables and identify potential impacts.
Excellent planning, organizing and time management skills, with the ability to develop and implement plans by prioritizing and multitasking.
Proven ability to work collaboratively in a team environment.
Effective leadership skills to provide support and guidance to team members.
Proficient with Microsoft Office Suite.
Demonstrate knowledge in agile practices, scrum, kanban and continuous delivery; e xperience in programming languages is considered an asset.
Willing and able to travel as required including to the United States/Canada.
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
[email protected] .
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.
