Senior Microsoft 365 Engineer

AHEAD

5d • Remote

About The Position

AHEAD builds platforms for digital business. By weaving together advances in cloud infrastructure, automation and analytics, and software delivery, we help enterprises deliver on the promise of digital transformation. At AHEAD, we prioritize creating a culture of belonging, where all perspectives and voices are represented, valued, respected, and heard. We create spaces to empower everyone to speak up, make change, and drive the culture at AHEAD. We are an equal opportunity employer, and do not discriminate based on an individual's race, national origin, color, gender, gender identity, gender expression, sexual orientation, religion, age, disability, marital status, or any other protected characteristic under applicable law, whether actual or perceived. We embrace all candidates that will contribute to the diversification and enrichment of ideas and perspectives at AHEAD. 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.

Requirements

• 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.
• 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).
• 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.

Nice To Haves

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

Responsibilities

• 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.
• 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.
• 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.
• 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.
• 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.

Benefits

• Medical, Dental, and Vision Insurance
• 401(k)
• Paid company holidays
• Paid time off
• Paid parental and caregiver leave

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed