About Us At CAA Club Group, we are passionate about keeping our Memberssafe - whether they are on the road, at home, or travelling abroad.As atrusted Member-based organization, we provide products and services that are essential to Members’ safety and peace of mind. With over 2.6 million Members across Ontario and Manitoba, we advocate on issues such road safety and infrastructure, the workplace, seniors’ mobility, and consumer protection. Associates share in each other’s successes, drive change and support each other while cultivating a great working environment to deliver on what is best for our Members. CAA SCO Systems & Services Inc. is a member of the CAA Club Group of Companies.

About Us At CAA Club Group, we are passionate about keeping our Memberssafe - whether they are on the road, at home, or travelling abroad.As atrusted Member-based organization, we provide products and services that are essential to Members’ safety and peace of mind. With over 2.6 million Members across Ontario and Manitoba, we advocate on issues such road safety and infrastructure, the environment, seniors’ mobility, and consumer protection. Associates share in each other’s successes, drive change and support each other while cultivating a great working environment to deliver on what is best for our Members. CAA SCO Systems & Services Inc. is a member of the CAA Club Group of Companies.

Who We Are Are you ready to join an award-winning, purpose-driven culture? Welcome to the CAA Club Group of Companies (CCG), where purpose leads to passion!

At CCG, we are committed to delivering an exceptional Associate experience. We offer:

Work-life harmony with access to an award-winning holistic wellness program,

Continuous learning through our robust corporate curriculum and education reimbursement program,

Incredible rewards, travel incentives, and product and service discounts,

Pay-for-performance and best-in-class recognition programs, and

Competitive benefits that include a defined contribution plan, personal spending account, and so much more.

Join our growing team where everyone belongs!

Position Details What You Will Do

Own end-to-end delivery of digital, mobile, roadside, membership, travel,



and enterprise application initiatives

Establish and execute application roadmaps aligned with business objectives

Lead Development Managers and technical teams responsible for design, development, testing, deployment, and continuous improvement

Ensure high-quality delivery through strong governance, release management, and delivery practices

Lead production support and application operations across Club technology platforms

Establish service management processes including incident, problem, change, and release management

Define SLAs, operational KPIs, monitoring, alerting, and escalation procedures

Lead major incident management and executive communications during service disruptions

Lead modernization of legacy platforms and migration to cloud-native architectures

Promote adoption of modern technologies including cloud, containers, microservices, APIs, event-driven architectures, and AI-enabled capabilities

Guide application architecture decisions to ensure scalability, security, performance, and maintainability

Oversee modernization roadmaps, technical debt reduction, and platform lifecycle management

Provide strategic oversight for enterprise integrations, APIs, middleware, and event-driven solutions

Ensure integration platforms support business growth, reliability, and interoperability requirements

Ensure compliance with security, privacy, accessibility, and governance requirements.

Establish resource plans and portfolio investment strategies, developing and managing operating and capital budgets

Manage strategic vendor relationships, contracts, statements of work, and service providers

Ensure strong governance over external partners and managed service providers

Please note, salary range is not inclusive of total compensation.



The expected salary range for this position will be impacted by factors such as the successful candidate’s skills, experience and working location, as well as the specific position’s business line, scope and level. Candidates with salary expectations outside of the range are encouraged to apply.

Who You Are

Bachelor's degree in Computer Science, IT, Engineering, or a related discipline

Master's degree in IT, Business Administration, or related field is considered an asset

12+ years of progressive IT experience in application development, delivery, and support

5+ years of leadership experience managing managers and multi-disciplinary technology teams

Proven experience leading enterprise application portfolios

Experience managing digital platforms, mobile applications, APIs, integrations, and customer-facing solutions

Strong experience with cloud-native and container platforms such as OpenShift and Kubernetes

Experience with DevOps, CI/CD, observability, and automated testing

Experience managing technology budgets, vendor agreements, and transformation programs

Experience supporting business-critical 24x7 environments

Experience with modern development technologies including: React, Next.js, Java, Spring Boot, REST APIs, Microservices, BFF Architecture

Preferred Certifications

PMP, ITIL, SAFe or Agile certifications, Microsoft Azure Certifications, AWS or Google Cloud Certifications, TOGAF or Architecture certifications, CISSP or Security-related certifications

Our Commitment We are an equal opportunity employer and are committed to providing employment accommodation in accordance with all applicable Provincial Human Rights and Accessibility Legislation. CCG will provide accommodations to job applicants with disabilities throughout the recruitment process. If you require an accommodation, please notify us and we will work with you to meet your needs.

Please note that internal applicants are asked to formally express their interest by applying online no later than 10 business days of the position being posted.

Please note that we may use AI tools to help us through the recruitment process.

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📌 Director, Application Delivery & Support (Winnipeg)
🏢 CAA Club Group
📍 Winnipeg