PMO Manager

Winslow Technology Group; Rhode Island; Hybrid; USD 125,000 - 150,000; Full time

Job summary

Winslow Technology Group seeks an experienced Professional Services PMO Manager to lead our Project Management team, balancing 60% PMO leadership with 40% direct customer delivery. You will ensure consistent PMO standards, oversee health across Professional Services and Co-Managed Services, and drive successful customer engagements.

The role requires 10+ years in project management in IT services, strong leadership, and a PMP/Prince2 credential.

Qualifications

• 5+ years of direct management of employees (PMs)
• 10+ years of project management experience in IT services
• Bachelor's degree or equivalent
• PMP or Prince2 certification
• At least one technical PM specialization

Responsibilities

• Lead, coach, and develop the Project Management team with regular 1:1s and performance reviews.
• Ensure consistent PMO processes, workflows, templates, and reporting.
• Oversee portfolio health, schedules, risks, and customer escalations.
• Own sales-to-delivery transitions and scope validation.
• Manage financials: change orders, billing milestones, and forecasting.
• Maintain customer satisfaction and continuity between projects and Co-Managed Services.
• Direct PMO and delivery for assigned engagements (40%).

Skills

Project management

Leadership

Stakeholder management

Communication

Education

Bachelor's Degree or equivalent experience

PMP or Prince2 Certification

Tools

Autotask PSA

Job description

Position Summary

The Professional Services PMO Manager is responsible for leading our Project Management team while directly managing customer projects and Co-Managed Services engagements. The role is approximately 60% PMO leadership and team management / 40% direct customer delivery. This position owns the consistency, visibility, and effectiveness of project delivery across Professional Services and Co-Managed Services, connecting Sales, Solutions Architecture, Engineering, Finance, customers, and Professional Services Leadership.

Primary Responsibilities

PMO & Team Leadership

• Lead, coach, develop, and hold accountable the Project Management team through regular 1:1s, performance management, training, and professional development.
• Monitor workload, productivity, utilization, time tracking, and overall execution.
• Establish and enforce consistent project management processes, workflows, templates, documentation, reporting, and communication standards.
• Provide oversight and quality assurance across projects managed by the PM team.
• Recruit and develop Project Management resources as needed.

Portfolio & Delivery Oversight

• Maintain visibility across the full Professional Services and Co-Managed Services portfolio, including project health, schedules, aging, dependencies, blocked work, resource conflicts, customer concerns, and delivery risk.
• Identify stalled engagements and drive appropriate escalation and corrective action.
• Provide leadership with clear, concise visibility into portfolio and customer health.
• Participate directly in customer escalations, project recoveries, and executive discussions when appropriate.
• Identify engineering delivery or accountability concerns and elevate through the appropriate leadership channels.

Sales-to-Delivery Transition

• Own the transition from Sales and Solutions Architecture into delivery through the internal kickoff process.
• Validate scope, assumptions, prerequisites, dependencies, resource requirements, schedules, and customer expectations before execution.
• Ensure unclear or incomplete requirements are addressed before they become delivery issues.
• Support a consistent transition from project implementation into ongoing Co-Managed Services.

Commercial & Financial Management

• Identify scope creep and initiate appropriate review and change-order activity.
• Oversee preparation and coordination of project change orders.
• Track and forecast milestone billing and trigger invoicing with Finance.
• Ensure Project Managers appropriately track contractual, financial, and delivery milestones.
• Escalate conditions that may negatively affect project completion, billing, or financial performance.

Customer & Co-Managed Services Delivery

• Maintain a regular pulse on customer satisfaction and communicate simple Red/Yellow/Green health indicators.
• Develop strong professional relationships with customers and WTG Account Executives.
• Ensure recurring Co-Managed Services activities, including monthly and quarterly health checks, are proactively scheduled and tracked.
• Maintain continuity between Professional Services projects and ongoing Co-Managed Services engagements.
• Identify opportunities to improve customer communication, responsiveness, and overall delivery experience.

Direct Project Management | Approximately 40%

• Personally manage an assigned portfolio of customer projects and Co-Managed Services agreements.
• Lead kickoff, status, planning, and service-delivery meetings.
• Coordinate engineering resources, customer responsibilities, schedules, dependencies, and deliverables.
• Maintain project status, action items, risks, milestones, and escalations.
• Manage scope changes, change orders, and billing triggers for assigned engagements.
• Recognize when technical, customer, or delivery issues require escalation and engage the appropriate resources.

Ideal Background

• Experience leading Project Managers in an IT solutions provider, VAR, MSP, systems integrator, consulting, or Professional Services environment.
• Experience managing multiple concurrent customer-facing technology projects.
• Strong understanding of project delivery, resource coordination, scope management, change orders, milestone billing, and customer escalation.
• Ability to recognize when a technical engagement is becoming stuck without needing to be the technical subject-matter expert.
• Strong organizational, communication, leadership, and customer relationship skills.
• Experience with PSA or Professional Services automation platforms, preferably Autotask/Datto PSA.

What Success Looks Like

• Projects are consistently managed, visible, and professionally communicated.
• Project Managers follow a common process and are actively coached and developed.
• Delivery risks and stalled activities are identified early.
• Customers experience a consistent transition from project delivery into ongoing services.
• Change orders and billing milestones are handled promptly.
• Leadership has clear visibility into portfolio health and delivery risk.
• The PMO Manager remains directly connected to customer delivery while continuously improving how the broader team operates.

Required Experience

• 5+ years of experience with direct management of employees, ideally Project Managers
• 10+ years of Project Management Experience, ideally in an IT Solutions Provider / Consultancy setting
• Bachelor’s Degree or equivalent experience
• PMP or Prince2 Active / Maintained Certification
• At least one (1) technical PM specialization and related experience with demonstrated practical application

Position Type: Full-Time/Regular

Location / Travel Requirements: Primarily remote (ideal candidate is located in CT/MA/RI), occasional in-office meetings (Waltham, MA) and other in-person events.

Work authorization: United States (required)

Salary: $125,000+ (commensurate with experience, capabilities, and certifications)

Winslow Technology Group is an Equal Opportunity/Affirmative Action Employer