Lead cloud modernization and digital transformation for an insurance organization in the Greater Toronto Area. Guide scalable application platforms and delivery.

This IT Director provides strategic oversight across application development, operations, support, and enterprise technology portfolios. The role advances cloud-native architecture, technical debt reduction, and software delivery excellence. It also develops technology leaders while managing vendors, budgets, and transformation programs.

Key Responsibilities

Lead cloud modernization and technical debt reduction initiatives

Drive digital transformation and software delivery excellence

Build, mentor, and develop technology leaders and teams

Ensure security, governance, compliance, reliability, and scalability

Manage vendors,



technology budgets, and transformation investments

Requirements

12+ years of progressive IT experience

5+ years leading managers and multidisciplinary technology teams

Cloud-native architecture expertise with OpenShift and Kubernetes

Experience with Java, Spring Boot, microservices, and BFF architecture

Enterprise portfolio and large-scale transformation management experience

Lead cloud-native modernization while connecting governance, transformation, application delivery, and operational performance across enterprise technology.

📌 IT Director Cloud Transformation (Winnipeg)
🏢 Michael Page Canada
📍 Winnipeg