Senior Director, Enterprise Project Management Office

Staples Canada•Richmond Hill, ON

31d•Hybrid

About The Position

The Senior Director, Enterprise Project Management Office leads the enterprise-wide project, program, and portfolio management function to translate corporate strategy into measurable execution across all business units and functions. Operating as a senior leader within the Office of the Chief Information Officer, this role provides the governance, standards, and enterprise prioritization needed to ensure capital, people resources, and organizational capacity are allocated to the initiatives that matter most. The Senior Director oversees the end-to-end strategic investment lifecycle intake, prioritization, planning, execution oversight, risk management, and benefit realization to ensure the organization delivers intended outcomes and payback on its strategic investments. This role creates transparency, alignment, and disciplined execution across both business-to-business and business-to-customer portfolios.

Requirements

Bachelor’s degree in Business, Information Systems, Engineering, or related field required
10 + years in enterprise program, portfolio, or transformation leadership roles
Experience leading enterprise Project Management Office functions or transformation offices
Demonstrated success influencing senior executives and providing Board‑level reporting
Track record managing multi‑year investment portfolios with measurable outcomes
Experience implementing or maturing Project Portfolio Management tools and enterprise dashboards
Knowledge of Agile at scale and Waterfall delivery models
Strong financial acumen: capital planning, business case evaluation, Return On Investment /payback modeling, forecasting, scenario analysis
Expertise in enterprise portfolio governance, prioritization, and benefits realization

Nice To Haves

Master’s degree in business administration or engineering preferred
Professional certifications preferred: Project Management Professional /Projects in Controlled Environments, Portfolio Management Professional, Scaled Agile Framework/Agile, Professional Science (or equivalent)

Responsibilities

Lead the enterprise portfolio governance framework, ensuring prioritization and approval of initiatives based on strategic alignment, expected value, capacity, and risk.
Partner with cross functional departments to integrate strategy, capital planning, and budget cycles into a single enterprise planning calendar.
Drive alignment between strategy refresh, Business Initiative Committee governance, financial planning, and annual business planning.
The role maintains direct, influential relationships across the full executive leadership team and stewards' enterprise‑level investment decisions, overseeing and guiding a strategic portfolio representing up to one hundred million dollars in total organizational spend.
Translate multi‑year strategic priorities into an executable, financially aligned enterprise portfolio.
Establish and enforce enterprise project, program, and portfolio management standards, including gating, quality controls, and reporting expectations.
Lead the enterprise benefits realization framework, including Knowledge Performance Indicator baselining, value tracking, and validation of realized benefits.
Conduct independent assurance reviews for high‑risk or enterprise‑critical initiatives and oversee corrective action plans.