Senior SCCM Engineer

Job Title: Senior SCCM Engineer

Work Location: Remote

Type: Contract

Role Summary

• We are seeking a Senior SCCM Engineer with deep expertise in large scale Windows OS upgrade initiatives and advanced task sequence design. This role is responsible for architecting, executing, and optimizing enterprise grade Windows feature upgrades (e.g., Windows 10 → Windows 11) across complex, distributed environments with tens of thousands of endpoints.
• The ideal candidate is a task sequence expert who understands not just how to build OSD/IPU task sequences—but how to design them for scale, resiliency, telemetry, rollback, and zero touch execution in real world enterprise conditions. This role partners closely with Endpoint Engineering, Security, Service Desk, and Program leadership to ensure predictable, low risk outcomes.

Key Responsibilities

• Windows OS Upgrade & Deployment Leadership
• Lead large scale Windows feature upgrade programs (e.g., Windows 10 → Windows 11) using Microsoft Endpoint Configuration Manager (SCCM/ConfigMgr).
• Design and execute In Place Upgrade (IPU) strategies that minimize user disruption and maximize success rates.
• Own upgrade wave planning, readiness validation, pilot execution, phased rollouts, and enterprise cutover strategies.
• Partner with security, identity, and endpoint teams to ensure compliance, encryption, and device readiness throughout the upgrade lifecycle.
• SCCM Task Sequence Architecture (Expert Level)

 Architect and maintain complex SCCM task sequences for:

• In Place OS Upgrades (IPU)
• Bare metal and refresh scenarios (as needed)
• Pre flight checks, dynamic logic, and conditional branching
• Implement robust task sequence logic, including:
• Custom pre flight readiness validation
• Hardware, firmware, and BIOS gating
• Application compatibility handling
• Error detection, logging, and graceful failure paths
• Optimize task sequences for performance, resiliency, repeatability, and supportability at enterprise scale.

Application & Driver Readiness

• Coordinate application compatibility testing and remediation in support of OS upgrades.
• Manage driver strategies (dynamic driver injection, vendor models, fallback logic).
• Ensure applications, security agents, and management tools survive upgrades reliably.
• SCCM Infrastructure & Operations
• Support and optimize core SCCM components relevant to upgrade programs:
• Site systems (DPs, MPs, SUPs)
• Boundaries, collections, and deployment logic
• Content distribution and bandwidth optimization

• Troubleshoot upgrade failures using client logs, task sequence logs, and SQL data.
• Drive continuous improvement by analyzing failure patterns and hardening upgrade workflows.
• Monitoring, Reporting & Continuous Improvement
• Build and maintain upgrade success/failure dashboards and reporting.
• Use telemetry to improve task sequences, deployment rings, and readiness logic.
• Document standards, runbooks, and operational playbooks for repeatable execution.
• Collaboration & Leadership
• Act as a technical authority for Windows OS deployment within the endpoint engineering organization.
• Provide guidance and mentoring to junior engineers and offshore delivery teams.
• Engage with program managers, service desk leadership, and security stakeholders to align execution with business outcomes.

Required Qualifications

• Technical Expertise
• 7+ years of hands on experience with Microsoft Endpoint Configuration Manager (SCCM/ConfigMgr).
• Demonstrated success leading large enterprise Windows OS upgrade projects (10k+ endpoints).
• Expert level experience designing and troubleshooting SCCM task sequences, especially In Place Upgrades.

Strong knowledge of:

• Windows 10 / Windows 11 deployment and servicing
• Task sequence scripting and logic
• Client side logging and troubleshooting

• Advanced PowerShell skills for automation, validation, and remediation.
• Enterprise Endpoint Experience
• Experience working in complex, highly regulated enterprise environments.
• Familiarity with endpoint security controls (BitLocker, Defender, EDR tools) as they relate to OS upgrades.
• Understanding of patching, application deployment, and endpoint lifecycle management.

Preferred / Nice to Have

• Experience integrating SCCM with Intune / Co Management environments.
• Windows Autopilot or modern provisioning exposure (even if SCCM led today).
• Experience in managed services or global delivery models.
• Prior involvement in OS upgrades during mergers, divestitures, or large transformations.

What Success Looks Like

• Windows upgrades execute predictably, at scale, with minimal user impact.
• Task sequences are resilient, modular, and self healing.
• Failure rates decline over time through data driven improvement.
• The organization views OS upgrades as repeatable operations, not one off fire drills.