Technical program manager Jobs in Oakville, ON

Position Summary

:Reporting to the Director, Portfolio Management, you will act as the primary client liaison to lead the implementation of projects and program workstreams within the Strategic Delivery Office of PointClickCare. You will support multi-year enterprise transformation programs and/or individual projects governed by the SDO, ensuring alignment with transformation strategy and portfolio-level objectives. This role will be responsible for managing both standalone projects and workstreams embedded within larger transformation programs, requiring strong collaboration with Program Directors, Business stakeholders, OCM partners, PO’s and Enterprise Architecture teams.

Key Responsibilities:

• Enterprise Project & Program Delivery Leadership
• Own end-to-end delivery of complex projects and embedded workstreams within enterprise transformation programs:
• Act as primary client liaison for SDO-governed projects and programs
• Lead standalone projects and workstreams within multi-year, cross-functional transformation programs
• Ensure alignment with transformation strategy, portfolio objectives, and program roadmaps
• Maintain momentum, cohesion, and clear ownership across all workstreams
• Manage day-to-day operational execution, including task definition and resource allocation
• Participate in integrated planning rhythms across SDO programs
• Governance, Planning & Financial Management
• Apply PMO best practices to deliver projects on time, on budget, and in alignment with SDO governance standards:
• Develop and maintain project plans using PMO methodologies tailored to stakeholder needs
• Ensure adherence to SDO intake, prioritization, governance, and reporting standards
• Manage project scope, budget, timelines, and resourcing
• Assess and manage scope changes, including impact analysis on budget, schedule, and capacity
• Drive benefits realization by ensuring scope and solutions align to intended business outcomes
• Stakeholder, Executive & Vendor Management
• Enable informed decision-making through strong stakeholder engagement, executive communication, and vendor oversight:
• Communicate project status, milestones, budget tracking, and risks to executive sponsors and business stakeholders
• Own escalation and change control processes, ensuring timely resolution
• Prepare and maintain all project management reports using SDO-standard formats
• Contribute to portfolio dashboards and integrated program reporting
• Coordinate with vendors from SOW development through delivery
• Manage vendor onboarding, accountability to contract, deliverables, and timelines
• Lead vendor calls and maintains productive vendor relationships
• Risk, Change & Data-Driven Decision Management
• Proactively manage risk, change, and delivery insights to protect outcomes and enable adoption:
• Identify, assess, and manage project risks and issues with appropriate urgency
• Facilitate problem-solving by bringing the right stakeholders together and driving closure
• Own accountability for decision-making at the appropriate organizational level
• Integrate Organizational Change Management into project planning
• Partner with Program Change Directors on readiness, impacts, communications, adoption, and collision risks
• Leverage data-driven metrics and AI-enabled insights for forecasting, risk identification, and stakeholder communication
• PMO Capability Building & Organizational Contribution
• Strengthen enterprise delivery maturity through PMO capability development and continuous improvement:
• Build deep understanding of business functions and technical needs
• Foster growth of project management capabilities within the PMO
• Share best practices, tools, and lessons learned across teams
• Contribute to the overall goals and objectives of the Project Management Office
• Support adoption of project metrics, dashboards, and AI-assisted delivery tools

Required Skills & Experience:

• Experience:
• 5–10 years of professional project management experience in complex environments
• Demonstrated experience leading agile projects or programs end‑to‑end, including scope, schedule, budget, and resources
• Experience working in matrixed organizations with cross‑functional teams and shared accountability
• Proven experience managing project risks, issues, dependencies, and escalations
• Core Skills & Capabilities:
• Strong project planning and execution using PMO best practices and governance standards
• Ability to manage scope changes and clearly communicate impacts to budget, schedule, and resourcing
• Excellent stakeholder and executive communication skills, including status reporting and escalation management
• Strong analytical and problem‑solving skills, including basic root cause analysis
• High attention to detail, organization, and time management
• Proven experience delivering agile and waterfall projects and programs/initiatives
• Tools & Ways of Working:
• Proficiency with project management and productivity tools (, MS Office, JIRA, Aha! or similar)
• Experience gathering, analyzing, and reporting project metrics and dashboards
• Comfort working in data‑driven environments and interpreting metrics to inform decisions
• Experience working with AI‑assisted delivery, forecasting, or analytics tools
• Strong business acumen with the confidence to drive accountability and decision ownership at senior levels

Preferred Experience:

• Experience managing projects in one or more of the following areas:
• Enterprise-wide transformation programs
• Technology modernization projects
• Multi-vendor delivery projects
• Cross-functional multi-team delivery initiatives
• Experience delivering workstreams within enterprise‑wide, multi‑year transformation programs
• Experience supporting digital transformation, enterprise information management, or Corporate Data Office initiatives
• Experience partnering with Organizational Change Management (OCM) teams to manage readiness, adoption, and change impacts
• Demonstrated ability to integrate change management activities into project delivery
• PMP, Agile, or equivalent certification preferred

$139,000 - $155,000 a yearAt PointClickCare, base salary is one of the many components that make up our total rewards package. The Canada base salary range for this position is $139,000 - $155,000 + bonus + benefits,non-overtime eligible. Our salary ranges are determined by job and level. The range displayed on each job posting reflects the target for new hire salaries for the position across all Canada locations. Within the range, individual compensation is determined by job-related skills and knowledge, relevant experience including professional and lived experience, and/or work location.