Senior Project Manager

System One is a leader in delivering outsourced services and workforce solutions across North America. They are seeking a Senior Project Manager/Scrum Master who will drive large, complex, cross-functional initiatives from planning through delivery while blending Agile and Waterfall methodologies. The ideal candidate will lead project execution, manage risks, and ensure alignment between business goals and technical teams.

Responsibilities:

• Lead end-to-end delivery of complex projects across cross-functional teams
• Develop clear project plans, milestones, and deliverables aligned with business objectives
• Drive project execution by coordinating activities, monitoring progress, and ensuring accountability. Maintain focus on outcomes and business value, not just task completion
• Manage project/program deliverables to ensure completion on schedule, within scope, and within budget
• Direct and coordinate work plans, schedules, milestones, and deliverables
• Identify, communicate, and resolve cross-organizational issues that may impede project/program success
• Mentor and guide team members to support effective project/program execution
• Lead projects within an Agile delivery environment supporting iterative planning and sprint execution
• Work closely with product owners, technical leads, and development teams to align backlog priorities
• Facilitate Agile ceremonies including sprint planning, stand-ups, reviews, and retrospectives
• Utilize Azure DevOps (ADO) to manage work items, track progress, and monitor delivery metrics
• Ensure backlog grooming, sprint planning, and task tracking are maintained in Azure DevOps
• Analyze project challenges, dependencies, and constraints to determine the most effective path forward
• Anticipate risks early and develop mitigation strategies
• Challenge assumptions and ask questions that clarify objectives and improve outcomes
• Make sound, data-informed decisions when navigating ambiguity or competing priorities
• Serve as the central coordination point between project teams, leadership, and stakeholders
• Build strong cross-functional partnerships to ensure alignment and transparency
• Communicate project progress, risks, and decisions clearly
• Facilitate productive discussions that drive consensus and forward momentum

Requirements:

• 15+ years of experience managing complex projects or programs (at least 5 years in the agile world and 5 years in traditional waterfall delivery)
• Leading Agile delivery teams as the PRIMARY Scrum Master
• Hands-on experience using Azure DevOps (ADO) for backlog management and work tracking
• Demonstrated ability to lead cross-functional teams and drive execution
• Strong critical thinking and problem-solving abilities
• Exceptional communication and stakeholder management skills
• PMP and CSM/SSM certifications
• Experience working with enterprise technology or digital delivery teams
• Experience managing complex multi-team initiatives