Senior Technical Project Manager

Role: Senior Technical Project Manager, Windows Modernization

Location: Remote

Duration: 6+ Months

Job Summary:

Provide senior, deeply technical project leadership for an enterprise Windows modernization effort. The role will translate endpoint-engineering strategy into an executable roadmap and coordinate engineering, security, identity,  application, hardware, service management, and business teams through design, pilot, deployment, adoption, and stabilization.

Key Responsibilities

• Own the Windows modernization roadmap, integrated plan, deployment waves, dependencies, risks, governance, and success criteria.

• Partner closely with Windows endpoint engineering to coordinate architecture, management tooling, security baselines, identity, application compatibility, hardware readiness, and support processes.

• Lead discovery, current-state assessment, design decisions, pilot cohorts, test plans, deployment rings, rollback criteria, and enterprise rollout.

• Coordinate application owners, security, networking, identity, procurement, asset management, service desk, field support,  and business stakeholders.

• Drive executive governance, technical decision forums, RAID management, milestone reporting, resource planning, and escalation.

• Ensure end-user communications, change adoption, training, knowledge transfer, documentation, and operational readiness are complete.

• Use data and deployment telemetry to identify risk, improve rollout quality, and drive corrective action.

Required Skills and Experience

• 8+ years of technical project or program management experience, including enterprise endpoint or Windows transformation programs.

• Strong technical experience with Windows endpoints, endpoint engineering, device management, security baselines, application compatibility, and deployment operations.

• Demonstrated delivery of Windows upgrades, modern management, endpoint security, device lifecycle, or large-scale workplace modernization.

• Ability to engage credibly with senior engineers and translate technical decisions into integrated delivery plans.

• Experience with pilots, deployment rings, readiness criteria, telemetry, rollback, user adoption, and service transition.

• Advanced governance, executive reporting, risk management, Jira, schedule, and cross-functional leadership skills.

Preferred Qualifications

• Experience with Microsoft Intune, Configuration Manager, Windows Autopilot, Entra ID, Defender, or comparable endpoint technologies.

• Experience modernizing identity, device compliance, application packaging, patching, or endpoint privilege controls.

• PMP, PgMP, SAFe, or equivalent certification.

• Experience leading global endpoint programs across distributed environments.

Critical Competencies

• Windows Expertise
• Program Leadership
• Engineering Partnership
• Deployment Governance
• Data-Driven Decisions
• Risk Control
• Executive Influence
• Change Leadership

Success Measures

• Windows modernization waves meet technical, security, user-experience, and operational acceptance criteria.

• Application, hardware, identity, security, and support dependencies are resolved before rollout.

• Deployment telemetry, risk controls, rollback plans, documentation, and service ownership support a stable transition