The Role:
This role serves as the operational leader for CentralSquare's Professional Services organization, reporting to the VP of Professional Services. The Director is responsible for establishing, implementing, and enforcing a Project Management Office (PMO) that drives consistency, accountability, and excellence across 50+ Project Managers delivering customer implementations.
The Director owns the PMO framework including standardized methodologies, tools, templates, and governance processes that ensure projects are delivered on time, on budget, and with quality. This role establishes the operational cadence that provides leadership with visibility into delivery performance, resource utilization, and project health—and holds the PM organization accountable to those standards.
This is a hands-on leadership role that combines strategic thinking with disciplined execution, managing a team of Business Operations Managers and Resource Planners while building the systems and processes that enable a high-performing Services organization.
Job Duties Include:
PMO Establishment & Governance
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Establish and lead the Professional Services PMO, defining the standards, processes, and governance that drive consistent project delivery
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Develop and enforce standardized project management methodologies, tools, and templates across 50+ Project Managers
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Define project lifecycle stages, gate criteria, and approval processes for project initiation, planning, execution, and closure
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Establish and enforce standards for project documentation, status reporting, risk management, and change control
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Lead regular project reviews and audits to ensure compliance with PMO standards and identify coaching opportunities
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Drive adoption of PMO practices through training, communication, and change management
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Continuously improve PMO frameworks based on lessons learned, industry best practices, and organizational feedback
Operational Reporting & Metrics
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Design, implement, and continuously improve operational reporting that provides leadership with clear visibility into Professional Services performance
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Develop and maintain executive-level dashboards and reports including revenue recognition tracking, delivery pipeline status, project health, and resource utilization
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Track and report on implementation milestones, go-live schedules, and post-go-live items that impact revenue unlock
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Aggregate and analyze operational data from Salesforce, Power BI, and other systems to identify trends, blockers, and opportunities for improvement
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Partner with Services leadership to translate complex operational data into clear narratives that drive decision-making
Delivery Operations & Cross-Functional Coordination
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Establish and maintain the operational rhythm for Services leadership reviews, ensuring consistent preparation, documentation, and follow-through
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Track delivery blockers and coordinate with Product, Cloud, Development, and Customer Support teams to resolve cross-functional dependencies
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Facilitate issue resolution by escalating dependencies and ensuring follow-through on committed actions from other functional areas
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Provide operational support for customer escalations requiring Services intervention
Resource Planning & Capacity Management
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Oversee resource planning processes to ensure appropriate staffing for implementation projects
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Monitor utilization rates and capacity to support Services financial targets
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Partner with Services leadership on capacity planning and forecasting for annual operating planning
Process Improvement & Automation
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Lead initiatives to automate manual reporting processes, reducing preparation time and improving data accuracy
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Direct technical resources (internal or vendor) in building automated dashboards and reporting tools
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Benchmark operational performance against industry standards and recommend improvements
Team Leadership
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Lead and develop a team of approximately 5 Business Operations Managers and Resource Planners
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Set clear expectations, provide coaching, and conduct performance management for direct reports
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Ensure team members have the skills, tools, and support needed to deliver high-quality operational support
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Build team capacity to support the growth and evolution of Services operations
Requirements:
- Bachelor's degree in Business, Finance, Operations, or related field; MBA preferred
- 10+ years of experience in operations, program management, or PMO leadership, with at least 5 years in a leadership role
- PMP, PRINCE2, or equivalent project management certification required
- Proven experience establishing and running a PMO, including defining methodologies, governance, and standards
- Experience enforcing project management standards across a large PM organization (40+ project managers)
- Background in Professional Services operations, preferably in a software/SaaS environment
- Strong proficiency in Salesforce reporting, Power BI, and Microsoft Office Suite (particularly Excel and PowerPoint)
- Experience with PPM tools and project portfolio management practices
- Experience with operational metrics and KPIs including utilization, revenue recognition, and project delivery metrics
- Proven ability to translate complex data into clear executive communication
Top Skills
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