Director, PMO

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.

• 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…