• Lead the development of project plans, timelines, and budgets in collaboration with stakeholders, ensuring alignment with client objectives and business requirements • Own end-to-end delivery from kickoff through deployment, ensuring predictable outcomes. Build and manage integrated, dependency-driven project plans with clear critical path, ownership, and milestones. • Monitor project progress and proactively identify risks in advance and drive mitigation actions to maintain schedule, scope, and budget alignment. • Manage project financials and scope with discipline, including tracking against budget, identifying variances, and driving structured change control. Ensure all scope changes are documented, approved, and aligned to business and contractual expectations. Make informed tradeoff recommendations for balancing timeline, cost, and feature delivery. • Proactively manage stakeholder expectations and influence outcomes across Client Services, Product, and Technology. • Serve as a primary point of contact for clients, establishing and maintaining strong relationships to understand their needs, expectations, and concerns. • Communicate effectively with internal and external stakeholders, providing regular updates on project status, risks, and issues. • Lead decision-oriented stakeholder forums that drive alignment and assign clear accountability. Translate complex delivery details into concise, executive-ready narratives, including risks, tradeoffs, and required decisions. • Lead cross-functional project teams, providing direction, guidance, and support to team members throughout the project lifecycle. • Foster a collaborative team environment, promoting communication, teamwork, and accountability to achieve project goals. • Coach and mentor junior project managers and team members, fostering their professional growth and development • Ensure the quality of project deliverables meets or exceeds client expectations and industry standards. • Proactively identify and assess project risks and issues, developing and implementing risk mitigation and contingency plans as needed. • Conduct regular project reviews and audits to monitor compliance with project management processes and best practices. • Identify opportunities for process improvements and efficiency gains within the project management office. • Lead lessons learned sessions at the conclusion of projects to capture key insights and best practices for future initiatives. • Contribute to the development and refinement of project management methodologies, tools, and templates.

• Own daily Kanban board health for support and delivery operations. • Maintain visibility into intake, backlog, active work, blockers, aging items, dependencies, and completed work. • Coordinate routine technical support work across platform, product, engineering, and support stakeholders. • Help capture, triage, categorize, and route incoming support requests. • Facilitate standups, Kanban reviews, backlog refinement, weekly planning, and status checkpoints.

• Serve as a trusted partner and primary point of contact for enterprise customers throughout the project lifecycle. • Build strong relationships with multinational, multi-billion-dollar organizations through professionalism, communication, accountability, and consistent execution. • Lead customer-facing meetings, presentations, executive updates, and project reviews with confidence and clarity. • Develop and manage comprehensive project plans, timelines, milestones, deliverables, and resource coordination across multiple concurrent projects. • Ensure projects are delivered on time, within scope, and aligned to customer expectations and business objectives. • Coordinate cross-functional teams to ensure alignment, accountability, and successful execution. • Track project risks, dependencies, action items, and deliverables while proactively identifying solutions and mitigation strategies. • Adapt project plans and priorities as business needs and customer requirements evolve. • Provide consistent, professional communication to internal leadership teams and external customer stakeholders. • Prepare and present project status reports, executive summaries, timelines, and risk assessments. • Facilitate project meetings, drive action items, and maintain momentum across teams and stakeholders. • Build alignment and trust across departments, customers, and executive leadership. • Ensure project documentation, deliverables, and communications are organized, accurate, and accessible. • Maintain a strong focus on customer satisfaction, execution quality, and continuous improvement. • Support process optimization and operational efficiencies through modern tools, automation, and AI-enabled workflows where appropriate. • Opportunity to help drive Tillster’s evolution into an AI First/Native company focused on innovation, automation, and intelligent customer experiences.

Role Description We are partnering with a large government contracting and defense industry client seeking an experienced Senior IT Project Manager to lead a high-profile Microsoft Enterprise Agreement (EA) renewal initiative tied to a Microsoft G5 capability program. This is a strategic, enterprise-wide initiative within a GCC-High environment that will require strong leadership, executive communication, and the ability to coordinate across multiple technical and business teams. This role will serve as a key leader driving project execution while collaborating with internal stakeholders, executive leadership, and a third-party Service Integrator. The ideal candidate has successfully delivered multiple Microsoft G5-related initiatives in highly regulated environments and understands the complexity of enterprise technology deployments within the defense sector. The Senior IT Project Manager will be responsible for leading the planning, execution, coordination, and delivery of the Microsoft EA renewal and G5 capability program. This individual will oversee timelines, risks, stakeholder communication, and cross-functional collaboration to ensure successful delivery of program objectives. - Leading enterprise IT project delivery within a GCC-High environment - Managing Microsoft EA renewal initiatives and G5 capability deployment efforts - Coordinating activities across infrastructure, cybersecurity, compliance, operations, and business teams - Partnering with executive stakeholders and technical leadership to align priorities and delivery expectations - Managing relationships with third-party Service Integrators and external vendors - Facilitating meetings, executive updates, risk reviews, and status reporting - Driving issue resolution, dependency management, and escalation processes - Ensuring project governance, documentation, and delivery standards are maintained - Supporting organizational readiness, communication planning, and implementation activities Qualifications - 8+ years of IT Project or Program Management experience - Proven experience successfully delivering multiple Microsoft G5 projects - Strong experience working within GCC-High environments - Experience managing enterprise Microsoft licensing or Microsoft EA renewal initiatives - Ability to lead complex cross-functional initiatives across technical and business teams - Strong communication, facilitation, and executive presentation skills - Experience working with third-party Service Integrators and external vendors - Strong understanding of cybersecurity, compliance, and enterprise IT governance practices - Bachelor's degree required - PMP certification strongly preferred Preferred Experience - Experience supporting government contracting or defense industry environments - Familiarity with Microsoft security and compliance solutions - Experience managing enterprise transformation or modernization initiatives - Previous experience supporting highly regulated environments with security requirements Benefits - This is an opportunity to lead a highly visible enterprise initiative supporting a major defense industry organization. - The project offers exposure to executive leadership, cutting-edge Microsoft technologies, and large-scale enterprise transformation efforts within a mission-critical environment.