Date: Aug 26, 2026
Location: Winnipeg, MB (Hybrid), CA Dartmouth, NS (Hybrid), CA Moncton, NB (Hybrid), CA Vancouver, BC (Hybrid), CA Edmonton, AB (Hybrid), CA Hybrid - Canada, CA Montreal, QC (Hybrid), CA Calgary, AB (Hybrid), CA North York - Toronto, ON (Hybr, CA Kitchener, ON (Hybrid), CA
#job-location.job-location-inline { display: inline; }
Company: Wawanesa Insurance
Job ID: 10275
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; Wawanesa, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Lethbridge, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Quebec City, QC, Moncton, NB; Dartmouth; NS.
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 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: $90,000 - $115,000. 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, this role contributes to Wawanesa's success by designing, building, supporting, and enhancing cloud-based business applications, operational platforms, and automation solutions. The role combines application development, cloud engineering, DevOps, and technical leadership to improve operational efficiency, system reliability, and developer productivity.
This position serves as a senior technical resource within the Application Delivery team, acting as a subject matter expert for cloud platforms, enterprise integrations, operational automation, and production support. The role leverages modern technologies, including AI-assisted solutions, to improve incident diagnosis, operational processes, system observability, and team effectiveness while ensuring secure, scalable, and resilient business systems.
Job Responsibilites
Design, develop, test, and support software solutions across cloud platforms, integrations, operational tooling, and business applications.
Lead technical design discussions and provide guidance on architecture, cloud solutions, system integrations, and development best practices.
Prepare technical specifications and solution designs from business and technical requirements.
Design and implement automation solutions that streamline operational processes, reduce manual effort, and improve service reliability and efficiency.
Leverage AI-enabled technologies to enhance incident diagnosis, troubleshooting, operational support, knowledge discovery, and developer productivity.
Configure, maintain, and enhance cloud-based application environments and supporting platform services.
Design and implement integrations across AWS services and enterprise platforms using APIs and modern integration patterns.
Develop and maintain cloud-native solutions using AWS services and modern DevOps practices.
Implement and maintain monitoring, logging, alerting, and observability solutions to support operational excellence and production support.
Troubleshoot and resolve application, integration, infrastructure, and operational incidents while ensuring the performance, security, stability, and availability of business systems.
Participate in planning, retrospectives, and continuous improvement activities while promoting development, security, and operational best practices.
Create and maintain technical documentation, operational procedures, and knowledge-sharing materials.
Mentor Application Developers, promote knowledge sharing, and provide technical leadership across the team.
Research and recommend emerging technologies, tools, and practices that improve operational effectiveness and application delivery.
Perform other duties as assigned.
Qualifications
Completion of a post-secondary degree or diploma in Computer Science, Software Development, Computer Engineering, Information Technology, or equivalent experience.
7+ years of practical experience in software development, cloud engineering, DevOps, or enterprise application delivery.
Strong experience designing, developing, and supporting enterprise applications and integrations.
Experience working with APIs, web services (REST/SOAP), relational databases, and SQL.
Strong programming skills in one or more modern languages such as Java, Python, JavaScript, or TypeScript.
Experience working in AWS environments and cloud-native architectures.
Experience implementing automation solutions, DevOps practices, and operational tooling.
Experience with monitoring, logging, observability, and production support practices.
Understanding of AI and Generative AI technologies, including practical application of AI tools to improve operational efficiency, troubleshooting, automation, and developer productivity.
Strong analytical, problem-solving, and troubleshooting skills.
Excellent communication, collaboration, and stakeholder engagement skills.
Demonstrated ability to mentor, coach, and provide technical leadership to development teams.
Experience with Guidewire InsuranceSuite or Guidewire Cloud platforms, including configuration, integrations, cloud operations, or development practices.
Experience integrating enterprise platforms such as ServiceNow, Jira, Splunk, Datadog, or similar technologies.
Experience with cloud operations, platform engineering, or Site Reliability Engineering (SRE) practices.
Experience building AI-powered operational tools, automation frameworks, or internal productivity solutions.
AWS, Guidewire, or other relevant cloud certifications.
Experience working within the insurance industry.
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.
