Senior Microsoft 365 Engineer in Chicago, Illinois at AHEAD

Role Summary

The Sr Microsoft 365 Engineer - Intelligent Support SME is responsible for delivering vendor-alternative support across the Microsoft portfolio (Azure, Microsoft 365, Exchange Online, Teams, SharePoint, SQL, Windows Server, System Center, Dynamics, etc.). This role provides deep technical expertise, end-to-end incident ownership, proactive guidance for migrations and major changes, acting as a trusted advisor and primary escalation point for complex Microsoft issues.

Incident & Problem Management

• Provide technical support for Microsoft workloads, including remote diagnosis, debugging, and remediation of complex issues.
• Own incidents end-to-end: triage, troubleshooting, coordination with internal/external teams, and communication through resolution.
• Serve as an escalation point for critical (Sev 1/2) Microsoft incidents to ensure rapid restoration of service.
• Drive root cause analysis (RCA) for major incidents and implement corrective actions to prevent recurrence.

Proactive Support & Supportability Reviews

• Conduct supportability reviews for major Microsoft migrations and deployments (e.g., M365, Azure, Teams, SharePoint, Exchange, SQL).
• Provide design and configuration recommendations to ensure high availability, performance, and supportability.
• Participate in planning and supporting customer change windows related to Microsoft platforms.

Patching, Hotfixes & Maintenance

• Lead patching and hotfix deployment activities for Microsoft platforms, ensuring safe rollout and minimal downtime.
• Evaluate Microsoft advisories and updates; recommend appropriate patching strategies aligned to customer risk profiles.
• Coordinate with customers on maintenance windows, rollback plans, and post-change validation.

Customer & Vendor Collaboration

• Act as a trusted technical advisor to customers for all Microsoft-related issues and questions.
• Coordinate with Microsoft (when needed) for complex defect resolution while maintaining AHEAD’s “single point of contact” experience.
• Collaborate closely with Client Success Managers to prepare for QBR/EBR reviews and present technical health/performance metrics.

Documentation & Continuous Improvement

• Create and maintain technical documentation, runbooks, and knowledge base articles to improve first-contact resolution.
• Contribute to continuous improvement efforts around processes, tools, and automation for Microsoft support.
• Mentor junior engineers and cross-train peers on Microsoft technologies and best practices.

• Technical Expertise
  • Deep, hands-on experience with several of the following:
    • Microsoft 365 (Exchange Online, SharePoint Online, Teams)
    • Azure IaaS/PaaS services and networking
    • Windows Server & Active Directory
    • SQL Server and related data services
    • System Center, Intune/Endpoint Manager
  • Strong troubleshooting skills across OS, networking, identity, and application layers.
• Experience
  • 8+ years in a Microsoft-focused support, operations, or consulting role.
  • Experience in enterprise or service provider environments with 24x7 support expectations.
  • Background in incident, problem, and change management processes (ITIL desirable).
• Soft Skills
  • Strong customer-facing communication skills (verbal and written).
  • Ability to remain calm and structured during high-severity incidents.
  • Comfortable working in a multi-vendor context and prioritizing competing demands.

• Microsoft certifications such as:
  • Microsoft 365 Certified (e.g., Administrator, Messaging, Teams)
  • Azure Administrator / Azure Solutions Architect
  • Windows Server or Security-focused certifications

• SLA response and resolution compliance for Microsoft incidents.
• Percentage of Microsoft incidents resolved without vendor escalation.
• Reduction in recurrence of major Microsoft incidents.
• Successful completion of supportability reviews for major Microsoft changes.
• Customer satisfaction scores (CSAT) and feedback for Microsoft-related tickets.