Director, PMO

Upshop•Toronto, ON

About The Position

The PMO Director is responsible for leading Upshop’s Project Management Office and driving successful customer outcomes through operational excellence, portfolio governance, strategic leadership, financial discipline, and team development. This role serves as both a strategic leader and hands-on operator, ensuring projects are delivered on time, within budget, within scope, and with exceptional customer satisfaction while continuously improving the scalability, efficiency, and profitability of Professional Services. The PMO Director will lead a team of Project Managers and oversee project delivery standards, governance, resource planning, forecasting, reporting, and operational maturity. This leader will partner closely with Implementation, Customer Success, Product, Engineering, Sales, Finance, and Executive Leadership to ensure successful customer implementations and continuous improvement across the organization. The ideal candidate combines deep SaaS implementation experience, PMO leadership expertise, strong business and financial acumen, and a passion for helping retailers transform operations through technology.

Requirements

Bachelor’s degree in Business Administration, Information Systems, Technology, Project Management, or related field.
10+ years of experience in project, program, PMO, or delivery leadership roles.
Proven success leading customer-facing SaaS implementation teams and enterprise software deployments.
Experience developing and managing PMO governance frameworks, methodologies, standards, and operational processes.
Experience managing project portfolios, budgeting, forecasting, capacity planning, and operational performance metrics.
Strong executive communication, stakeholder management, and organizational leadership skills.
Demonstrated ability to collaborate across Professional Services, Product, Engineering, Customer Success, Sales, and Finance organizations.
Experience managing multiple complex customer initiatives simultaneously.

Nice To Haves

Retail grocery, food retail, convenience retail, restaurant, store operations, merchandising, or supply chain experience strongly preferred.
Experience delivering SaaS solutions to enterprise retail organizations.
Customer-facing consulting or implementation leadership experience.
PMP certification preferred.
Experience leading globally distributed project delivery teams.
Experience building or scaling PMOs in high-growth SaaS organizations.
Strong knowledge of Agile, hybrid delivery methodologies, and modern cloud software implementation practices.
Experience with Professional Services operational metrics including utilization, forecasting, margin management, backlog planning, and capacity management.
Experience creating Centers of Excellence and leading operational transformation initiatives.
Familiarity with project and services delivery platforms including Wrike, Salesforce, Jira, Microsoft Project, CRM platforms, resource planning solutions, and reporting/dashboard tools.
Experience leveraging automation, workflow optimization, and AI-enabled delivery capabilities.

Responsibilities

Lead and manage the Project Management Office, including portfolio governance, project methodologies, delivery standards, reporting, tools, and operational processes.
Develop and maintain PMO policies, templates, dashboards, KPIs, governance frameworks, and best practices.
Establish and enforce delivery standards that ensure consistent execution across customer engagements.
Maintain visibility into project portfolio health, resource allocation, risks, dependencies, and strategic priorities.
Serve as the primary escalation point for project delivery concerns and work cross-functionally to drive timely resolution.
Recruit, mentor, develop, and retain a high-performing team of Project Managers and PMO professionals.
Establish performance goals and provide regular coaching, feedback, and career development support.
Promote a culture of accountability, customer focus, collaboration, and continuous learning.
Ensure Project Managers consistently follow established delivery methodologies and governance requirements.
Drive team engagement, development planning, and organizational capability growth.
Ensure successful execution of customer implementation projects by overseeing schedule management, scope control, risk mitigation, issue resolution, stakeholder communication, and escalation management.
Lead strategic or high-visibility internal programs when appropriate.
Develop and promote repeatable implementation methodologies that improve delivery quality and implementation speed.
Partner with Implementation, Product, Engineering, and Customer Success teams to improve customer outcomes and accelerate time-to-value.
Drive continuous improvement initiatives based on lessons learned, project retrospectives, and operational metrics.
Partner with Professional Services leadership to improve utilization, forecasting accuracy, backlog management, delivery efficiency, and profitability.
Oversee capacity planning and resource allocation to ensure appropriate staffing across all projects.
Monitor portfolio performance through financial and operational metrics, including project budgets, resource utilization, forecasting, project margins, and delivery health.
Support governance around Statements of Work, change requests, implementation planning, and delivery commitments.
Develop executive-level reporting and dashboards that provide actionable insights into PMO and Professional Services performance.
Build trusted relationships with customer executives, business sponsors, and key stakeholders.
Serve as an executive escalation point for strategic customer engagements.
Partner with Customer Success leadership to support customer satisfaction, retention, and expansion objectives.
Interface regularly with executive leadership regarding project priorities, risks, resource needs, and business opportunities.
Communicate project portfolio status, key initiatives, and operational performance through executive reporting and governance forums.
Own PMO tooling strategy and adoption across the organization.
Drive effective use of project and operational systems, including Wrike, Salesforce, Jira, reporting platforms, and resource planning tools.
Identify opportunities for automation and process optimization across Professional Services.
Promote adoption of AI-enabled tools and workflows that improve delivery efficiency, reporting accuracy, and organizational visibility.
Continuously evaluate processes and systems to improve scalability and operational effectiveness.