CoPilot Program Manager

Program Manager - Microsoft CoPilot Roll Out6 Month ContractRemoteHourly Rate: $90-$100 depending on experience W-2 with Brooksource or 1099 - not open to C2CThe Program Manager will oversee the end-to-end health of a six-milestone, wave-based Microsoft 365 Copilot enablement rollout supporting a large-scale enterprise deployment (20,000+ users) for a Fortune 50 Healthcare Client. This role is responsible for driving cross-functional coordination, stakeholder engagement, executive reporting, risk and decision management, and overall delivery governance from mobilization through final transition and closeout. The ideal candidate brings strong program leadership, client-facing communication skills, and the ability to manage complex rollout activities while ensuring a smooth handoff to long-term client ownership.Job ResponsibilitiesLead end-to-end program management for a six-milestone, wave-based Microsoft 365 Copilot rollout, ensuring delivery stays aligned to scope, timeline, and client objectives.Track rollout progress, adoption signals, risks, decisions, and dependencies across monthly wave cycles (M1–M6).Manage overall program health, including milestone tracking, dependency management, risk identification, decision logging, and issue resolution across the full engagement lifecycle.Coordinate cross-functional teams and delivery stakeholders to support successful wave planning, launch readiness, enablement execution, and reporting activities.Facilitate stakeholder engagement and recurring checkpoint meetings to maintain alignment across client leaders, delivery teams, and supporting functions.Prepare and deliver executive readouts that communicate rollout progress, adoption trends, key risks, decisions required, and recommended next steps.Maintain and govern core program artifacts, including decision logs, risk logs, dependency tracking, status reporting, and closeout documentation.Support escalation management by proactively identifying delivery risks, driving resolution paths, and ensuring accountability for follow-up actions.Partner with enablement, reporting, and platform leads to ensure program alignment with operational readiness, reporting requirements, and long-term sustainability, without directly owning delivery of those workstreams.Drive final transition and closeout activities, including handoff planning, ownership alignment, asset packaging, and management transition to the client.Ensure the program concludes with clearly documented deliverables, accepted outputs, and a sustainable framework for long-term client ownership and maintenance.RequirementsProven experience in program management, project management, consulting, customer success, or a related client-facing delivery role.Proven ability to manage complex, cross-functional programs with multiple milestones, stakeholders, and dependencies.Experience leading enterprise technology rollouts, enablement programs, digital transformation efforts, or large-scale adoption initiatives.Strong executive communication skills, including experience preparing and presenting status updates, readouts, and recommendations to senior stakeholders.Demonstrated experience maintaining governance artifacts such as risk logs, decision logs, dependency trackers, and action registers.Ability to proactively identify issues, manage competing priorities, and drive programs forward in fast-paced environments.Strong collaboration and relationship management skills with both internal delivery teams and external clients.Experience supporting transition planning, operational handoff, or program closeout activities is preferred.Familiarity with Microsoft 365, Copilot enablement, enterprise software rollout programs, or large-scale adoption/change initiatives (10K+ users preferred).Bachelor’s degree in business, communications, technology, project management, or a related field preferred.