Director, PMO

Role overview

Upshop is looking for a PMO Director to lead its Project Management Office and strengthen the way customer projects are delivered. This position blends strategic leadership with hands-on execution, with accountability for delivery quality, portfolio oversight, financial discipline, and team growth. The objective is to ensure work is completed on schedule, stays within budget and scope, and delivers a strong customer experience while improving the efficiency, scalability, and profitability of Professional Services.

The role oversees project managers and sets the standard for delivery governance, planning, reporting, forecasting, and operational maturity. You will work closely with Implementation, Customer Success, Product, Engineering, Sales, Finance, and executive leaders to drive successful customer rollouts and broader organizational improvement.

The ideal professional brings extensive SaaS implementation background, PMO leadership expertise, commercial awareness, and a strong drive to help retailers modernize operations through technology.

Core responsibilities

• Run the PMO function, including governance, delivery methods, reporting routines, tools, templates, and operating processes.
• Create and maintain PMO policies, dashboards, KPIs, standards, and best-practice frameworks.
• Set clear delivery expectations so customer engagements are executed consistently.
• Track portfolio status, staffing allocation, project risks, dependencies, and key priorities.
• Act as the main escalation contact for delivery issues and coordinate cross-functional resolution.
• Hire, coach, develop, and retain a high-performing group of project managers and PMO team members.
• Set goals, provide feedback, and support career development and capability building.
• Encourage accountability, collaboration, customer orientation, and continuous learning within the team.
• Make sure project managers follow the approved delivery approach and governance requirements.
• Lead important customer implementations by managing timelines, scope, risks, issues, communications, and escalations.
• Take ownership of strategic or high-visibility internal initiatives when needed.
• Build repeatable implementation approaches that improve speed and quality of delivery.
• Work with Implementation, Product, Engineering, and Customer Success to improve outcomes and shorten time-to-value.
• Use lessons learned, retrospectives, and performance data to drive continuous improvement.
• Partner with Professional Services leadership to improve utilization, forecasting, backlog control, delivery efficiency, and profitability.
• Oversee capacity planning and resource assignment so projects are properly staffed.
• Monitor budget, utilization, forecast accuracy, margins, and overall delivery health across the portfolio.
• Support governance for statements of work, change requests, implementation plans, and delivery commitments.
• Prepare executive-level reporting and dashboards for PMO and Professional Services performance.
• Build strong relationships with customer executives, sponsors, and key stakeholders.
• Serve as an executive escalation point for important customer engagements.
• Work with Customer Success leadership to support satisfaction, retention, and expansion goals.
• Keep executive leadership informed on priorities, risks, staffing needs, and business opportunities.
• Present portfolio status, initiatives, and operational performance in governance and leadership forums.
• Own the PMO technology strategy and drive organization-wide adoption.
• Promote effective use of systems such as Wrike, Salesforce, Jira, reporting tools, and resource planning platforms.
• Look for automation and process improvement opportunities across Professional Services.
• Encourage use of AI-enabled tools and workflows to improve efficiency, reporting, and visibility.
• Continuously assess systems and processes to improve scale and operational effectiveness.

Required qualifications

• Bachelor’s degree in Business Administration, Information Systems, Technology, Project Management, or a related discipline.
• At least 10 years of experience in project, program, PMO, or delivery leadership roles.
• Proven track record leading customer-facing SaaS implementation teams and enterprise software rollouts.
• Experience creating and running PMO governance models, methodologies, standards, and operating processes.
• Background in portfolio management, budgeting, forecasting, capacity planning, and operational performance tracking.
• Strong executive communication, stakeholder management, and leadership abilities.
• Ability to work across Professional Services, Product, Engineering, Customer Success, Sales, and Finance.
• Experience handling several complex customer initiatives at the same time.

Preferred background

• Experience in retail grocery, food retail, convenience retail, restaurants, store operations, merchandising, or supply chain is highly desirable.
• Experience delivering SaaS products to enterprise retail customers is a plus.
• Customer-facing consulting or implementation leadership experience is preferred.
• PMP certification is preferred.
• Experience leading project teams across multiple geographies is an advantage.
• Experience scaling or building PMOs in fast-growing SaaS companies is valuable.
• Knowledge of Agile, hybrid delivery methods, and modern cloud implementation practices is helpful.
• Familiarity with Professional Services metrics such as utilization, forecasting, margin, backlog, and capacity management is preferred.
• Experience creating Centers of Excellence and leading operational change initiatives is a plus.
• Comfort with platforms such as Wrike, Salesforce, Jira, Microsoft Project, CRM tools, resource planning systems, and reporting/dashboard software is beneficial.
• Exposure to automation, workflow optimization, and AI-enabled delivery capabilities is an asset.

Work context

This is a full-time onsite role based in the Greater Toronto Area, Canada.

Additional notes

No salary, stipend, start date, application deadline, number of openings, or internship duration was specified in the source information.