Program Manager – Senior

Job Title: Program Manager - Senior

Location: Toronto, Ontario, Canada

Work Model: Hybrid

Duration: 12 months

Extension: 1 Time

Must Haves

• 15+ years of demonstrated experience leading and overseeing program digital strategy definition from inception through to project close-out and any required transition to operations, business planning, benefits identification and organization funding requests for I&IT programs.(HM looking for strategic experience)
• 10+ years of demonstrated experience understanding and articulating I&IT executive expectations and translating into program deliverables
• 15+ years experience directing, managing and leading multidisciplinary project teams including multiple Project Managers, each responsible for an element of the project and associated matrix team members
• 15+ years experience providing a program/portfolio view of project inter-dependencies and external project dependencies, monitoring and reporting on exposure levels
• Significant experience with change management and transformation principles and best practices

Description / Responsibilities / Skills

Description

• Senior Program Manager to provide senior-level oversight, coordination and delivery management across multiple workstreams that support Modernization Programme.
• Ensure integrated planning, disciplined execution, timely escalation of issues and risks, and sustained alignment across internal and external partners.
• Provide program management leadership and expertise of large scale, highly complex, high profile and high-risk initiatives that may be multi-jurisdictional and/or enterprise-wide.
• Ensure accountability for the program's centralized group of projects and their successful full life cycle delivery.
• Ensure programs are delivered cost effectively and efficiently, and in compliance with organization's methodologies, standards and frameworks.

Desired Skills

• Deep experience with Agile, SAFe, or product operating models; ability to shift teams from project mindset product mindset.
• Proven ability to identify and execute cost savings and efficiency opportunities; experience with technology rationalization.
• Using data to drive decisions (KPIs, OKRs, transformation metrics); comfort with data strategy, governance, and analytics enablement.

Rated Criteria

• Demonstrated experience leading complex digital transformation with effective use of AI, automation, data, and enabling technologies to improve delivery and operational efficiency.
• Demonstrated experience preparing high-quality briefing notes, presentations, reports, and decision materials for executive audiences.
• Demonstrated ability to lead portfolio-level process improvements, operational optimization, and implementation of new delivery models.
• Demonstrated experience working within public sector or health system environments, with understanding of governance, accountability, policy, and funding structures.

Deliverables

• Define program strategy and roadmap, including implementation plan, to ensure strategic choices drive a harmonized approach to concurrent workstreams
• Design program governance and oversee regularly scheduled touchpoints with both workstream leads, Director Sponsors and Senior Leaders
• Author policies, standards, guidelines and procedures to support implementation of the work
• Develop and oversee change management strategy to ensure awareness, desire, knowledge, ability and reinforcement objectives are met
• Define monitoring and measurement framework to assess health of program efforts, processes and outcomes
• Conduct facilitated workshops, engagement sessions and other key activities to support employees and leaders in making progress against defined goals

Experience & Skill Set Requirements

Rated Criteria

• Demonstrated experience leading and coordinating complex digital transformation and multi-workstream initiatives with multiple stakeholders, including the effective use of AI, automation, data, and enabling technologies to improve delivery, decision-making, and operational efficiency. Experience developing integrated workplans, clarifying roles and priorities, managing dependencies and risks, and ensuring alignment and coordinated delivery across concurrent initiatives and governance structures. 20 Points
• Demonstrated experience preparing high-quality briefing notes, presentations, reports, and decision materials for executive audiences. Proven ability to facilitate discussions, build consensus, and drive alignment and decisions across business, clinical, policy, vendor, and delivery stakeholders for digital transformation. 20 Points
• Demonstrated ability to lead portfolio-level digital transformation process improvements, operational optimization, and implementation of new delivery models, including the application of formal change management methodologies to support adoption and implementation across complex programs. 20 Points
• Demonstrated experience working within public sector or health system environments, with an understanding of governance, accountability, policy considerations, and funding structures that influence program and delivery decisions. 20 Points

Desired Skills Transformation & Strategic Leadership

• Ability to define and drive multi-year transformation roadmaps aligned to business outcomes
• Experience with operating model redesign (product-centric vs project-based, platform models)
• Clear linkage between technology investments and measurable value (ROI, OKRs)

Desired Skills Cloud & Modern Architecture Fluency

• Solid understanding of cloud platforms (Azure/AWS/GCP) and migration patterns (rehost, refactor, replatform)
• Knowledge of modern architectures: microservices, APIs, event-driven, data platforms
• Familiarity with FinOps and cloud cost governance
• Ability to guide application rationalization and tech stack consolidation

Desired Skills AI & Automation Enablement

• Practical understanding of AI/ML use cases (not just theory) and where they drive value
• Experience accelerating AI adoption (governance, responsible AI, data readiness)
• Identifying and scaling automation opportunities (RPA, workflow automation, copilots)
• Balancing innovation vs. risk, ethics, and compliance

Desired Skills Delivery Excellence (Product + Agile at Scale)

• Deep experience with Agile, SAFe, or product operating models
• Driving value-based delivery (prioritization tied to outcomes, not just outputs)
• Strong execution rigor: planning, RAID management, governance, metrics
• Ability to shift teams from project mindset product mindset

Desired Skills Financial & Operational Optimization

• Proven ability to identify and execute cost savings and efficiency opportunities
• Experience with technology rationalization (apps, vendors, platforms)
• Strong grasp of business cases, funding models, and benefits tracking
• Vendor and partner management (including SI oversight)

Desired Skills Stakeholder & Influence Skills (Critical differentiator)

• Executive communication-translating tech into business impact
• Influencing across business + IT + external partners without direct authority
• Navigating complex org dynamics and competing priorities

Desired Skills Data & Decision-Making Mindset

• Using data to drive decisions (KPIs, OKRs, transformation metrics)
• Comfort with data strategy, governance, and analytics enablement

Required Skills (non-duplicate)

• 10+ years of progressive leadership experience in the capacity of coach and developer of all levels of talent