Program Management Office Lead

Insight Global; Toronto; On-site; CAD 180,000 - 240,000; Full time

Job summary

Insight Global in Toronto seeks a Director, GIS PMO to lead day-to-day PMO operations and ongoing development, partnering with executives and delivery teams to drive portfolio execution, governance, financial management, and risk mitigation across large-scale transformation programs.

The role requires a proven track record delivering enterprise programs, building cross-functional teams, and communicating with executives to ensure predictable outcomes and alignment of strategy with execution.

Qualifications

• Undergraduate degree in Business, Science, Engineering or equivalent.
• 10+ years progressive project and program management experience.
• 5+ years in a PMO leadership role, managing enterprise programs and teams.
• Proven success leading large-scale transformations and cross-functional programs.
• Experience operating at the executive level and building high-performing teams.
• Strong financial and portfolio management including budgeting, forecasting and cost control.
• Experience leading PMO governance, risk management, reporting and controls.
• Executive communication, presentation, and influencing skills.
• Ability to balance enterprise strategy with operational execution.
• Strong stakeholder management across business, technology, leaders, and external vendors.
• People leadership including hiring, coaching, succession planning and retention.

Responsibilities

• Lead day-to-day operations and continued PMO development.
• Oversee portfolio execution, governance, and financial management.
• Plan resources, deliver projects, and manage PMO talent.
• Partner with executives, business leaders, delivery teams, and vendors to drive outcomes.
• Improve transparency, manage risk, and resolve delivery challenges.
• Drive predictable outcomes across large-scale transformation initiatives.

Skills

Leadership

Executive communication

Stakeholder management

Financial management

PMO governance

Portfolio management

Talent development

Cross-functional leadership

Risk management

Education

Undergraduate degree in Business, Science, Engineering

Job description

The Director, GIS Project Management Office will lead the day-to-day operations and continued development of the enterprise PMO, serving as a key member of the GIS Leadership Team. This individual will oversee portfolio execution, governance, financial management, resource planning, project delivery, and PMO talent. The role will partner closely with executives, business leaders, delivery teams, and external vendors to improve transparency, manage risk, resolve delivery challenges, and drive predictable outcomes across large-scale transformation and strategic initiatives

Required Skills & Experience

• Undergraduate degree in Business, Science, Engineering, or an equivalent field
• 10+ years of progressive project and program management experience
• 5+ years of experience in a PMO leadership role, managing enterprise-level programs and teams
• Demonstrated success leading large-scale transformations and complex, cross-functional programs
• Proven experience operating effectively at the executive level
• Experience building and leading high-performing, cross-functional teams
• Strong financial and portfolio management experience, including budgeting, forecasting, investment tracking, and cost control
• Experience leading PMO governance, delivery frameworks, risk management, reporting, and project controls
• Strong executive presence with excellent communication, presentation, negotiation, and influencing skills
• Ability to balance enterprise strategy with operational execution
• Strong stakeholder management skills across business, technology, leadership, and external vendor groups
• People leadership experience, including hiring, onboarding, coaching, talent development, succession planning, performance management, and retention

Nice to Have Skills & Experience

• PMP certification
• PgMP certification
• Agile certification or experience
• SAFe certification or experience
• Lean certification or experience
• Experience improving PMO operating models, methodologies, tools, processes, and delivery capabilities
• Experience developing executive dashboards and portfolio performance reporting
• Experience supporting audit-ready project and program practices
• Experience advising executives on delivery strategy, organizational readiness, prioritization, and delivery trade-offs

*We may use artificial intelligence tools to assist with the screening, assessment, or selection of potential applicants for this position.

Vacancy:

This posting is for a currently vacant role, and the successful candidate will be hired into an existing open position.