MSP Project Management Leader

This role oversees day-to-day project operations, develops project managers, manages project priorities, and partners closely with Engineering, Service Desk, Client Success, Sales, and Billing to deliver an exceptional customer experience. The Project Management Leader is responsible for leading Cortavo's Project Management team and ensuring the successful delivery of customer implementations and professional services projects.

Job Overview:


The Project Management Leader is responsible for leading Cortavo's Project Management team and ensuring the successful delivery of customer implementations and professional services projects. This role oversees day-to-day project operations, develops project managers, manages project priorities, and partners closely with Engineering, Service Desk, Client Success, Sales, and Billing to deliver an exceptional customer experience.
This is a hands-on leadership position. The Project Management Leader is expected to coach the team, remove roadblocks, improve operational processes, monitor project health, and serve as the escalation point for customer implementations. While they may occasionally manage strategic projects, their primary responsibility is building a consistent, scalable project delivery function through their team.

The Project Management Leader reports directly to the Chief of Staff and indirectly to the CEO.

Responsibilities:
Team Leadership

• Lead, coach, and develop the Project Management team through regular 1:1s, performance feedback, and career development
• Set clear expectations, priorities, and performance goals for Project Management team
• Conduct hiring, onboarding, performance evaluations, and corrective action as needed
• Foster a culture of ownership, accountability, collaboration, and continuous improvement
• Balance workloads and ensure projects are appropriately assigned

Project Delivery

• Oversee the successful execution of customer projects, including:
• New client onboarding
• Microsoft 365 and Azure migrations
• Infrastructure upgrades
• Security implementations
• Office relocations
• Hardware deployments
• Network projects
• Professional services engagements
• Serve as the primary escalation point for implementation issues
• Ensure customer expectations are managed appropriately throughout delivery
• Monitor the health of the project portfolio and proactively identify risks
• Review project plans, milestones, budgets, and resource assignments
• Conduct post-project reviews to identify lessons learned and process improvements.
• Remove blockers and escalate issues when appropriate
• Standardize project documentation, templates, and workflows
• Drive adherence to established project management processes and SOPs
• Partner with leadership on resource planning and project forecasting

Cross-Functional Collaboration
Partner closely with:

• Sales
• Review project scope during handoffs
• Identify implementation risks before project kickoff
• Improve sales-to-delivery transitions
• Engineering
• Coordinate technical resources
• Resolve scheduling conflicts
• Improve implementation quality
• Client Success
• Ensure successful customer transitions
• Support expansion opportunities following project completion
• Finance & Billing
• Ensure projects are ready for billing
• Improve project profitability
• Track change orders and scope adjustments

Process Improvement

• Continuously improve the effectiveness of the project management team by:
• Identifying operational bottlenecks
• Improving project templates and documentation
• Streamlining project workflows
• Increasing resource utilization
• Reducing implementation delays
• Improving cross-functional communication
• Recommend improvements to leadership based on project performance data

Reporting & Metrics

• Maintain visibility into department performance through regular reporting on key metrics, including:
• Active projects
• Project backlog
• Resource capacity
• On-time delivery
• Customer satisfaction

Required Skills & Qualifications

• Bachelor's degree or equivalent experience
• 5+ years of project management experience in an MSP, IT services, or technology consulting environment
• 2+ years of experience leading or mentoring project managers or project coordinators
• Proven experience managing multiple concurrent customer implementations
• Strong understanding of managed services delivery and customer onboarding
• Excellent organizational, communication, and leadership skills
• Ability to prioritize competing demands in a fast-paced environment

Preferred Qualifications

• PMP certification
• ITIL Foundation certification
• Experience with Halo PSA or a comparable PSA platform
• Experience with Microsoft 365, Azure, networking, and cybersecurity projects

Estimated Usage of Time

• 30% Team Leadership (1:1s, coaching, performance management, hiring)
• 30% Project Delivery (status reviews, prioritization, removing blockers, customer escalations)
• 15% Process Improvement (templates, SOPs)
• 15% Cross-Functional Collaboration (engineering, sales, client success, accounting)
• 10% Resource Planning & KPI Reporting

Work Environment

• Competitive salary, as well as employer, contributed health benefits
• Hybrid work schedule
• Access to a Company cell phone plan
• A seat on an energetic team that collaborates and pushes each other to be better
• A fast-paced but cooperative environment with endless potential for growth
• Celebration events for team and Company successes throughout the year