Senior Systems Engineer - Microsoft 365 Architecture and Identity

Engagement: Contract

Employment Type: 1099

Location: Remote

Position Overview

The Senior Systems Engineer – Microsoft 365 Architecture, Identity & Migrations is a subject matter expert responsible for architecting, administering, and optimizing Microsoft 365 with a primary focus on M365 architecture, Entra ID (Azure AD), hybrid identity (Active Directory on-prem, ADFS, Entra Connect), and migration/tenant engineering programs.

This role leads complex initiatives such as tenant-to-tenant migrations, tenant consolidations, Exchange mailbox migrations, and SharePoint/OneDrive migrations, including domain cutovers and identity mapping. As a senior technical resource, this individual ensures the performance, security, and availability of Microsoft 365 services while partnering with infrastructure, security, compliance, and business stakeholders to support digital transformation outcomes.

Key Responsibilities

• M365 Architecture & Tenant Engineering: Define and implement Microsoft 365 tenant architecture, governance, and standards across Exchange Online, Teams, SharePoint Online, and OneDrive to ensure scalability, performance, and strong end-user experience.
• Entra ID (Azure AD) & Access Controls: Administer Entra ID with emphasis on Conditional Access, MFA, role-based access controls, and audit-aligned access policies.
• Hybrid Identity: Support and optimize hybrid identity environments including Active Directory (on-prem), ADFS, and Azure AD Connect / Entra Connect (sync health, staging, filtering, troubleshooting).

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• Migration & Tenant Work (primary focus): Lead M365 migrations and consolidations including tenant-to-tenant, Exchange mailbox migrations (cutover/staged/hybrid), and SharePoint/OneDrive migrations, including domain cutovers and identity mapping to ensure service continuity.
• Migration Tools & Vendor Management: Plan and execute migrations using BitTitan, Quest, and ShareGate; coordinate with vendors and Microsoft support to resolve issues and optimize outcomes.
• Exchange & Email Security: Manage mail flow, connectors, and email security controls including SPF/DKIM/DMARC and Defender capabilities (as applicable).
• Security & Compliance: Configure and maintain M365 compliance features (DLP, retention, eDiscovery, litigation hold) and support audits (e.g., SOX).
• Automation: Build and maintain PowerShell automation for administration, identity lifecycle workflows, reporting, and pre/post-migration validation.
• Collaboration & Mentorship: Serve as a technical escalation point and mentor team members on M365, identity, and migration best practices.

Required Qualifications

• Strong experience with Microsoft 365 architecture and tenant engineering (Exchange Online, Teams, SharePoint Online, OneDrive).
• Deep expertise in Entra ID (Azure AD) and identity/access controls, including Conditional Access and MFA.

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• Hands-on experience with Active Directory (on-prem) and hybrid identity patterns.
• Experience supporting ADFS and federated authentication flows (as applicable).
• Strong experience with Azure AD Connect / Entra Connect (sync configuration, filtering, staging mode, troubleshooting).
• Proven experience executing Microsoft 365 migrations, including:
• Tenant-to-tenant migration and tenant consolidation
• Exchange mailbox migrations (cutover / staged / hybrid)
• SharePoint / OneDrive migrations
• Domain cutover and identity mapping
• Experience with migration tooling such as BitTitan, Quest, and ShareGate.
• Proficiency in PowerShell scripting for Microsoft 365 administration, automation, and reporting.
• Solid understanding of email security standards (SPF, DKIM, DMARC) and Microsoft Defender (as applicable).
• Familiarity with M365 compliance capabilities (eDiscovery, retention, DLP) and SOX-related IT controls.
• Strong understanding of network and DNS concepts as they relate to cloud services (DNS, TCP/IP, VPN), especially for mail flow and domain cutover scenarios.