Lead technology modernization at WSIB as an IT Project Director, guiding complex portfolios across applications, infrastructure, data, and cybersecurity.

This 12-month temporary individual contributor role reports to the Senior Director, IT Portfolio & Project Management. You will translate a five-year technology heatmap and remediation roadmap into executable projects. Success requires senior program leadership, dependency management, governance, and stakeholder alignment.

Key Responsibilities

Lead concurrent technical projects across multiple technology domains

Translate modernization priorities into sequenced delivery plans

Manage dependencies, risks, issues, constraints, and competing priorities

Provide governance, reporting, escalation, and senior leadership communication





Coordinate technical resources and address delivery constraints

Requirements

Seven to ten-plus years of senior project management experience

Experience leading complex, interconnected technology initiatives

Experience delivering applications, infrastructure, data, or cybersecurity projects

Experience managing significant budgets, ideally five million dollars or more

University degree or equivalent relevant experience; PMP certification is an asset

Bring technology delivery, governance, and modernization leadership to WSIB’s complex multi-year remediation portfolio.

📌 Senior IT Program Director Modernization (Winnipeg)
🏢 Workplace Safety and Insurance Board (WSIB)
📍 Winnipeg