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Role overview

The Director of PMO will oversee Upshop’s Project Management Office and play a central role in delivering strong customer results through disciplined execution, portfolio oversight, operational leadership, financial rigor, and people development. This position blends strategy with day-to-day ownership, ensuring work is completed on schedule, within scope and budget, and at a level that supports excellent customer experience. The role also focuses on making Professional Services more scalable, efficient, and profitable over time.

The leader in this position will manage a team of Project Managers and set the bar for delivery practices, governance, staffing plans, forecasting, reporting, and operational maturity. They will work closely with teams across Implementation, Customer Success, Product, Engineering, Sales, Finance, and senior leadership to support successful customer deployments and drive ongoing improvement across the business.

The strongest fit will bring deep experience in SaaS implementations, PMO leadership, commercial and financial judgment, and a genuine interest in helping retailers improve operations through technology.

PMO leadership and governance

Direct the PMO function, including portfolio oversight, delivery methods, operating standards, reporting, tools, and core processes.
Build and refresh PMO policies, templates, dashboards, KPI tracking, governance models, and best-practice frameworks.
Set clear delivery expectations and ensure consistent execution across all customer workstreams.
Maintain a clear view of portfolio status, staffing allocation, risks, interdependencies, and strategic priorities.
Act as the main escalation contact for delivery issues and coordinate cross-functional resolution.

Team leadership and people development

Hire, coach, develop, and retain a strong group of Project Managers and PMO professionals.
Set performance objectives and provide ongoing feedback, mentoring, and career growth support.
Encourage a culture built on accountability, customer orientation, collaboration, and continuous learning.
Make sure Project Managers follow the established delivery approach and governance requirements.
Strengthen team engagement, development plans, and overall organizational capability.

Delivery excellence

Oversee customer implementation work to ensure timelines, scope control, risk handling, issue resolution, communication, and escalation management are effective.
Lead high-priority or highly visible internal initiatives when needed.
Create and refine repeatable implementation approaches that raise delivery quality and speed up deployment.
Work with Implementation, Product, Engineering, and Customer Success to improve customer outcomes and shorten time-to-value.
Use retrospectives, lessons learned, and operational data to drive continuous improvement.

Professional services operations and financial management

Work with Professional Services leadership to improve utilization, forecast accuracy, backlog management, delivery efficiency, and profitability.
Oversee capacity planning and resource allocation so projects are properly staffed.
Track portfolio performance using financial and operational measures such as budgets, utilization, forecasts, margins, and delivery health.
Support governance for statements of work, change requests, implementation planning, and delivery commitments.
Create executive-level dashboards and reporting that provide clear insight into PMO and Professional Services performance.

Customer and executive leadership

Develop strong relationships with customer executives, sponsors, and other key stakeholders.
Serve as an executive escalation point for strategic customer accounts.
Partner with Customer Success leadership to support satisfaction, retention, and growth goals.
Communicate regularly with executive leadership on priorities, risks, resourcing needs, and business opportunities.
Present portfolio status, major initiatives, and operating performance in governance and executive forums.

Business process, systems, and innovation

Own the PMO tooling strategy and drive adoption across the organization.
Promote effective use of tools and systems such as Wrike, Salesforce, Jira, reporting platforms, and resource-planning software.
Spot opportunities to automate and streamline Professional Services processes.
Encourage the use of AI-enabled tools and workflows that improve delivery efficiency, reporting quality, and visibility.
Regularly assess systems and processes to increase scalability and operational effectiveness.

Required qualifications

A 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.
Strong track record leading customer-facing SaaS implementation teams and enterprise software rollouts.
Experience designing and managing PMO governance structures, standards, methodologies, and operating processes.
Background in portfolio management, budgeting, forecasting, capacity planning, and performance measurement.
Excellent executive communication, stakeholder management, and leadership abilities.
Ability to collaborate effectively across Professional Services, Product, Engineering, Customer Success, Sales, and Finance.
Proven experience managing several complex customer initiatives at the same time.

Preferred qualifications

Experience in grocery retail, food retail, convenience retail, restaurants, store operations, merchandising, or supply chain is highly desirable.
Experience delivering SaaS solutions to enterprise retail customers.
Background in customer-facing consulting or implementation leadership.
PMP certification is an advantage.
Experience leading globally distributed delivery teams.
Experience building or expanding PMOs in fast-growing SaaS companies.
Strong understanding of Agile, hybrid delivery approaches, and modern cloud implementation practices.
Knowledge of Professional Services metrics such as utilization, forecasting, margin management, backlog planning, and capacity management.
Experience creating centers of excellence and leading operational transformation programs.
Comfort with delivery platforms and systems such as Wrike, Salesforce, Jira, Microsoft Project, CRM tools, resource planning systems, and reporting dashboards.
Experience using automation, workflow improvement, and AI-enabled delivery capabilities.

Additional notes

This role is based in Toronto, Ontario, Canada and is a full-time onsite position. No salary or stipend details were provided in the source.

Director, PMO

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