Director of PMO Transformation & Strategy

Role Overview

The Director of PMO Transformation & Strategy will build and lead Woodcraft Rangers' first formal Project Management Office, establishing the systems, standards, and governance structures that enable the organization to deliver its strategic priorities with consistency and visibility. Reporting directly to the Senior Director of Operations and serving as a key member of the operations leadership team, this role is equal parts strategic advisor, operational architect, and delivery leader. The Director will oversee a growing PMO team, partner with department heads across the organization, and serve as the connective tissue between organizational strategy and on-the-ground execution.

Responsibilities

• PMO leadership & strategy
• Design, launch, and continuously improve Woodcraft Rangers' PMO, including its charter, methodology, governance model, and service offerings
• Build and maintain a portfolio dashboard that gives executive leadership real-time visibility into the health of strategic initiatives
• Develop the project intake and prioritization process, ensuring organizational resources are directed toward the highest-impact work
• Chair or co-chair the PMO steering committee in partnership with the Senior Director of Operations; prepare and present quarterly portfolio reviews to operations and executive leadership
• Define and track PMO KPIs — including on-time delivery rate, budget variance, and stakeholder satisfaction — and report on them transparently
• Establish and promote adoption of project management standards, templates, and processes across the organization, including project charters, RAID logs, status reporting, and stage gates
• Define decision rights, escalation paths, and approval workflows for projects of all sizes
• Develop a tiered governance model that applies appropriate oversight to projects based on size, complexity, and strategic importance
• Maintain the PMO charter and ensure it remains current as the organization's strategy evolves
• Lead or support high-priority cross-functional initiatives during the PMO’s early build phase to establish standards and demonstrate value
• Transition ownership of initiatives to operational leaders as PMO systems and capabilities mature
• Work with the AD of Strategic Operations to pilot projects that demonstrate the value of PMO standards and generate proof points for broader organizational adoption
• Identify and resolve cross-project resource conflicts, risks, and blockers; escalate to the Senior Director of Operations when executive decisions are required
• Ensure lessons learned from completed projects are captured and fed back into evolving PMO standards
• Build a PMO team structure appropriate to the organization’s stage, scaling roles and specialization over time. Partner with the Associate Director of Strategic Operations to define clear lanes of ownership; leverage their institutional knowledge and organizational relationships during the PMO's build phase
• Coach project managers across the organization, raising overall PM maturity and capability over time
• Build a culture of accountability, continuous improvement, and psychological safety within the PMO
• Partner closely with the Senior Director of Operations to align initiative prioritization, resource allocation, and execution support with broader operational strategy and capacity
• Build trusted relationships with department heads, program leaders, and executive sponsors across the organization
• Develop and execute an internal communications strategy that helps the broader organization understand the PMO's value and how to engage with it
• Proactively identify and manage PMO skeptics; convert reluctant stakeholders through demonstrated value rather than compliance
• Serve as a strategic thought partner to the COO on organizational priorities, capacity, and execution risk
• Build and maintain the organization’s execution systems, including project intake, portfolio tracking, and reporting tools
• Ensure alignment between project management systems and broader operational infrastructure
• Continuously improve tools and workflows that support cross-department coordination and execution
• Analyze cross-functional workflows to identify inefficiencies and improve how work is coordinated and executed across teams

Qualifications/Skills

• 8+ years of progressive experience in project management, strategic operations, or a related field, with at least 3 years in a leadership role
• Strong track record of delivering complex, cross-functional initiatives on time and within budget
• Exceptional stakeholder management skills; proven ability to influence senior leaders and hold teams accountable without direct authority
• Strong data fluency — comfortable building and interpreting portfolio dashboards, KPI tracking, and resource utilization analysis
• Excellent written and verbal communication skills
• Experience designing governance models, decision-rights frameworks, and portfolio reporting structures
• Ability to build and maintain a portfolio dashboard that gives executive leadership real-time visibility into the health of strategic initiatives
• Experience developing and implementing project management standards, templates, and processes across the organization
• Experience resolving cross-project resource conflicts, risks, and blockers; escalating to the Senior Director of Operations when executive decisions are required
• Experience capturing and feeding back lessons learned from completed projects into evolving PMO standards
• Experience building and maintaining a PMO team structure appropriate to the organization’s stage, scaling roles and specialization over time
• Experience coaching project managers across the organization, raising overall PM maturity and capability over time
• Experience building and maintaining a culture of accountability, continuous improvement, and psychological safety within the PMO
• Experience partnering closely with the Senior Director of Operations to align initiative prioritization, resource allocation, and execution support with broader operational strategy and capacity
• Experience developing and executing an internal communications strategy that helps the broader organization understand the PMO's value and how to engage with it
• Experience proactively identifying and managing PMO skeptics; converting reluctant stakeholders through demonstrated value rather than compliance
• Experience serving as a strategic thought partner to the COO on organizational priorities, capacity, and execution risk
• Experience building and maintaining the organization’s execution systems, including project intake, portfolio tracking, and reporting tools
• Experience ensuring alignment between project management systems and broader operational infrastructure
• Experience continuously improving tools and workflows that support cross-department coordination and execution
• Experience analyzing cross-functional workflows to identify inefficiencies and improve how work is coordinated and executed across teams