Senior Microsoft 365 Engineer

About the Role

Senior Microsoft 365 Engineer to serve as the technical lead for our M365 and identity platforms. This is a 100% remote position. This is a high-impact role supporting our aggressive acquisition strategy. You'll be the technical escalation point and subject matter expert for our M365 & Identity team, leading enterprise-scale tenant-to-tenant migrations, providing technical mentorship, and working closely with InfoSec, Legal, and business stakeholders to deliver secure, scalable, and compliant solutions. This role requires a self-directed problem-solver who proactively identifies challenges and drives solutions to completion with minimal supervision.

What You'll Do

• Lead large-scale tenant-to-tenant migrations for Exchange Online, OneDrive/SharePoint, and Teams using BitTitan MigrationWiz or Quest; own the entire lifecycle from planning and pre-migration assessments through cutover coordination and stabilization.
• Serve as the technical escalation point and SME for Microsoft Entra ID, Active Directory Domain Services, Exchange Online, Teams, and Microsoft Purview; provide Tier 3 support and technical guidance to build team capability.
• Own identity lifecycle management, Conditional Access/MFA implementation, hybrid sync (Entra Connect), and certificate services (AD CS, public certificates) to ensure seamless and secure access across the enterprise.
• Build and maintain M&A integration playbooks for M365 and identity services; document repeatable workflows to accelerate future acquisitions and reduce migration risk.
• Operate and improve Defender for Office 365 security controls (anti-phishing, Safe Links/Attachments); partner with InfoSec to tune policies, triage alerts, and close security gaps.
• Support Legal team with Microsoft Purview eDiscovery operations (legal holds, searches, exports) and maintain appropriate access controls and audit trails.
• Develop PowerShell and Microsoft Graph automation to reduce manual work, improve consistency, and enable scale for our growing environment.
• Create and maintain technical documentation, runbooks, architecture diagrams, and SOPs; ensure knowledge is captured for incident response and team continuity.
• Drive continuous improvement through proactive security gap identification, automation initiatives, and implementation of M365 best practices.
• Participate in Change Advisory Board (CAB), lead post-incident RCA, and maintain operational discipline through change control and incident management processes.

What You Bring

• 7–10+ years of hands-on Microsoft 365 engineering experience in an enterprise environment (or 5+ years with clear evidence of senior-level ownership and large-tenant impact).
• Proven hands-on experience leading complex tenant-to-tenant migrations with deep technical proficiency in BitTitan MigrationWiz, Quest, or similar migration platforms; experience managing multi-phase migrations, coexistence configurations, and minimal-disruption cutovers.
• Deep expertise in Exchange Online (mail flow, hybrid configurations, transport rules), Microsoft Entra ID (Conditional Access, MFA, PIM), and Entra Connect/AD Connect operations.
• Strong experience with Defender for Office 365 operations, Microsoft Purview eDiscovery, and enterprise compliance/retention policies.
• Advanced PowerShell scripting and automation skills; experience with Microsoft Graph API and Azure Automation for administration and reporting.
• Experience with certificate lifecycle management, PKI (AD CS), and hybrid authentication trust chains.
• Self-directed problem-solver with proven ability to diagnose complex technical issues independently and deliver results with minimal supervision.
• Strong communication skills with ability to translate technical concepts for non-technical stakeholders and lead outage calls under pressure.
• Bachelor's degree in information technologies or equivalent combination of experience and relevant IT certifications.
• Bonus: Power Platform experience (Power Apps, Power Automate) for internal process automation, Microsoft certifications, M&A integration experience.

Location and Work Arrangement

This is a 100% remote position. Candidates must be based in the United States and able to work during US business hours (with flexibility for global escalations). While you can work from anywhere in the US, Eastern or Central time zones are preferred for team collaboration.

Travel: This position may require occasional travel (up to 20%) for site visits, migration cutovers, M&A integration activities, and team meetings. Most work will be conducted remotely.