Job Description

Overview

We are seeking a highly experienced

Senior Project Manager

to lead the planning and preparatory activities for a major, multi-year technology modernization initiative. This role is dedicated exclusively to the

planning phase

--laying the strategic, technical, and organizational foundation required for a successful future transformation program.

The program aims to modernize a legacy application portfolio by transitioning into a secure, cloud-based, scalable, and supportable environment. The Senior Project Manager will drive planning efforts that reduce technical debt, enhance service delivery, and align with enterprise digital transformation and sustainability objectives.

This role does

not

include implementation responsibilities. Instead, the focus is on leading comprehensive planning, strategic assessments, readiness activities, and cross-organizational coordination.

Key ResponsibilitiesStrategic Planning & Program Readiness

Develop detailed project plans, governance frameworks, and planning roadmaps. Coordinate strategic, technical, and operational readiness assessments. Support the development of modernization strategies, cloud transition pathways, and supporting frameworks.

Data Analysis & Decision Support

Collaborate with technical teams to gather and analyze data to inform strategic decision-making. Interpret assessment findings and provide recommendations on technical and financial preparedness for future execution phases.

Stakeholder Engagement & Change Readiness

Facilitate stakeholder consultations, workshops, and readiness sessions. Lead change management planning to ensure organizational preparedness for upcoming transformation activities. Manage sensitive situations with political acuity and ensure alignment with enterprise-level objectives.

Cross-Functional Coordination

Work across teams to ensure infrastructure, software, security, and support models align with modern standards and cloud-first strategies. Coordinate inputs from IT, business units, architecture, and governance teams to ensure integrated planning.

Qualifications & ExperienceMust-Have Requirements

10+ years of experience

in project management within complex, multi-year technology programs. Expertise in applying project management theory, methodologies, and techniques to plan and guide enterprise-scale initiatives. Experience developing and managing complex projects, including resource estimation and preparation/presentation of submissions for approval. Demonstrated

political acuity

, with ability to manage sensitive issues and collaborate effectively with government stakeholders. Knowledge of

IT systems, tools, and databases

used to develop comprehensive implementation plans, specifically including

Azure, cloud migration, and on-premise to cloud modernization

.

Nice-to-Have Experience

Previous experience within the

Ontario Public Service (OPS)

or similar government environment. Experience with

Corporate Governance

,

Treasury Board Submissions

, or executive-level reporting.

Skills & CompetenciesProject Management (40%)

Advanced knowledge of project management methodologies, governance, risk/issue management, and change management. Ability to lead large, multi-disciplinary planning initiatives.

Leadership & Political Acuity (20%)

Strong leadership to guide cross-functional teams through planning stages. Ability to manage multiple complex issues simultaneously. Skilled in navigating politically sensitive situations and aligning projects with government priorities.

Analytical & Strategic Thinking (20%)

Strong analytical skills and ability to examine trends, organizational context, and data to shape strategy. Ability to think holistically and horizontally across programs and functional areas.

Communication & Relationship Management (20%)

Excellent communication, negotiation, and facilitation skills. Ability to build strong relationships with internal and external stakeholders. Skilled at preparing briefing notes, presentations, planning documents, and reports. Strong proficiency with

Office 365, MS Teams, MS Project, Word, Excel, PowerPoint, and Visio

.
Job Types: Full-time, Fixed term contract
Contract length: 12 months

Pay: From $75.00 per hour

Application question(s):

How many years of experience do you have applying project management theory, methodologies, and techniques to lead complex enterprise projects? How many years of experience do you have developing and managing complex projects, including resource estimation and preparing/presenting submissions for approval? How many years of experience do you have working in environments that require high political acuity, including engaging with government stakeholders and managing sensitive situations? How many years of experience do you have working with IT systems, tools, and databases to develop implementation plans--specifically involving Azure, cloud migration, or on-premise-to-cloud modernization?
Location:

Toronto, ON (preferred)
Work Location: Hybrid remote in Toronto, ON