Program Manager, Business & Technology Transformation - Insurance client 3386

S.I. Systems Ltd.; Toronto, Winnipeg; Hybrid; CAD 90,000 - 130,000; Full time

Job summary

S.I. Systems Ltd. is seeking a Program Manager for Business & Technology Transformation for an Insurance client.

The role leads large, complex programs spanning multiple years, coordinating across business units, technology teams, and project managers to deliver strategic outcomes. Hybrid work arrangement (3 days on-site) in Toronto, London or Winnipeg, with a 12-month duration. Responsibilities include building governance, roadmaps, business cases, budgets, benefits realization, executive

Qualifications

• Extensive experience managing large projects and complex programs.
• Proven ability to deliver multiple related projects with significant business impact.
• Experience developing business cases, roadmaps and integrated plans with accountability for outcomes.
• Strong budgeting, cost management and resource allocation skills.
• Experience influencing senior/executive stakeholders and resolving conflicts.

Responsibilities

• Develop program strategies, roadmaps and business cases aligned with business goals.
• Lead delivery across related projects with governance and controls.
• Manage integrated plans, dependencies, priorities across scope/cost/schedule/resources.
• Own program budgets and coordinate with Finance on investments and reporting.
• Define and monitor benefits realization to maintain business value.
• Build relationships with senior leaders and delivery teams, resolve conflicts.
• Provide integrated executive reporting on progress, risks and outcomes.
• Collaborate with architecture teams to align with standards.
• Coordinate release readiness and change strategies across domains.
• Coach project managers and teams on delivery issues.

Skills

Large project management

Program governance

Stakeholder management

Budgeting and financial acumen

Decision making in ambiguity

Education

University or college education in Project Management or Business Administration

Job description

Program Manager, Business & Technology Transformation - Insurance client 3386

Program Manager, Business & Technology Transformation - Insurance client 3386

Duration: 12 Months

Location: Toronto, London or Winnipeg (Hybrid, 3x/week)

Overview:

Lead large, complex business and technology programs, often spanning multiple years and related projects. Coordinate delivery across business units, technology teams and project managers to achieve strategic objectives and benefits beyond those achievable through individual projects.

Responsibilities

• Develop program strategies, roadmaps and business cases aligned with business goals, ensuring each underlying project has a defined business case and contributes to program outcomes.
• Lead coordinated delivery across related projects, establishing governance, delivery standards, decision‑making structures and appropriate controls.
• Manage integrated plans, dependencies and competing priorities across scope, schedule, cost, resources, quality and risk.
• Own program budgets and resource planning. Partner with Finance on capital-versus-expense treatment of investments and accurate financial reporting.
• Define and monitor benefits realization, adjusting program priorities and delivery plans to maintain strategic alignment and business value.
• Build relationships with senior business and technology leaders, sponsors and delivery teams. Resolve stakeholder conflicts, cross-project issues and competing resource demands.
• Provide integrated executive reporting on program progress, financials, risks, decisions, outcomes and benefits.
• Assess impacts on people, processes, systems and products, including changes that require new approaches or departures from existing practices.
• Collaborate with enterprise, business and solution architecture teams to align delivery with architecture standards and information models.
• Coordinate release readiness, compatibility across delivery domains, system quality and organizational change strategies. Ensure stakeholder and customer issues are resolved.
• Coach project managers and multidisciplinary teams, provide guidance on complex delivery issues, and contribute to resource assignment, performance and development discussions.
• Adapt and improve program management practices, processes and tools while maintaining audit, compliance, risk and organizational governance requirements.

Must Haves

• Extensive experience managing large projects and complex programs. Ideal experience profile: 10+ years managing large projects, including 3+ years managing complex programs.
• Proven delivery of multiple related projects or workstreams with significant business impact and interdependent business and technology components.
• Experience developing business cases, program roadmaps, estimates and integrated plans, with accountability for business outcomes and benefits.
• Strong business, technical and financial acumen, including program budgeting, cost management and resource allocation.
• Experience influencing senior and executive stakeholders across business units, resolving conflicts and aligning teams with competing priorities.
• Strong understanding of program governance, risk assessment, controls and technical dependencies across systems and initiatives.
• Ability to make sound decisions with incomplete information, navigate ambiguity, constructively challenge established approaches and adapt to changing requirements.
• Experience adapting project/program management methodologies, coaching teams, supporting organizational change and improving delivery practices.
• University or college education in Project Management, Business Administration or a related field, or an equivalent combination of education and experience.

Nice to Haves

• Relevant industry certification such as PMP, PRINCE2 or PgMP.

Program Manager, Business & Technology Transformation - Insurance client 3386

Program Manager, Business & Technology Transformation - Insurance client 3386

Duration: 12 Months

Location: Toronto, London or Winnipeg (Hybrid, 3x/week)

Overview:

Lead large, complex business and technology programs, often spanning multiple years and related projects. Coordinate delivery across business units, technology teams and project managers to achieve strategic objectives and benefits beyond those achievable through individual projects.

Responsibilities

• Develop program strategies, roadmaps and business cases aligned with business goals, ensuring each underlying project has a defined business case and contributes to program outcomes.
• Lead coordinated delivery across related projects, establishing governance, delivery standards, decision‑making structures and appropriate controls.
• Manage integrated plans, dependencies and competing priorities across scope, schedule, cost, resources, quality and risk.
• Own program budgets and resource planning. Partner with Finance on capital-versus-expense treatment of investments and accurate financial reporting.
• Define and monitor benefits realization, adjusting program priorities and delivery plans to maintain strategic alignment and business value.
• Build relationships with senior business and technology leaders, sponsors and delivery teams. Resolve stakeholder conflicts, cross-project issues and competing resource demands.
• Provide integrated executive reporting on program progress, financials, risks, decisions, outcomes and benefits.
• Assess impacts on people, processes, systems and products, including changes that require new approaches or departures from existing practices.
• Collaborate with enterprise, business and solution architecture teams to align delivery with architecture standards and information models.
• Coordinate release readiness, compatibility across delivery domains, system quality and organizational change strategies. Ensure stakeholder and customer issues are resolved.
• Coach project managers and multidisciplinary teams, provide guidance on complex delivery issues, and contribute to resource assignment, performance and development discussions.
• Adapt and improve program management practices, processes and tools while maintaining audit, compliance, risk and organizational governance requirements.

Must Haves

• Extensive experience managing large projects and complex programs. Ideal experience profile: 10+ years managing large projects, including 3+ years managing complex programs.
• Proven delivery of multiple related projects or workstreams with significant business impact and interdependent business and technology components.
• Experience developing business cases, program roadmaps, estimates and integrated plans, with accountability for business outcomes and benefits.
• Strong business, technical and financial acumen, including program budgeting, cost management and resource allocation.
• Experience influencing senior and executive stakeholders across business units, resolving conflicts and aligning teams with competing priorities.
• Strong understanding of program governance, risk assessment, controls and technical dependencies across systems and initiatives.
• Ability to make sound decisions with incomplete information, navigate ambiguity, constructively challenge established approaches and adapt to changing requirements.
• Experience adapting project/program management methodologies, coaching teams, supporting organizational change and improving delivery practices.
• University or college education in Project Management, Business Administration or a related field, or an equivalent combination of education and experience.

Nice to Haves

• Relevant industry certification such as PMP, PRINCE2 or PgMP.