Microsoft 365 & Azure Licensing Specialist | CSP/GCC High | Advisory and Business Ops

Company Description

Agile IT is a Microsoft-centric cybersecurity consulting and managed services provider. We help customers migrate to, modernize, and secure Microsoft 365, Azure, Azure Government, and Microsoft GCC High environments—with a mission to make cybersecurity practical and sustainable through repeatable architectures, evidence automation, and managed operations. The majority of our clients are defense contractors preparing for or maintaining CMMC Level 2 certification.

Our Services

• Professional Services: Scoped projects to deploy, configure, migrate-to, and secure Microsoft cloud environments.
• Managed Services: Ongoing management and security operations including CMMC compliance support for Microsoft cloud and on-premises systems.
• GCC High Licensing & Onboarding: License sales, secure tenant provisioning, and lifecycle operations.

Job Description

Role Summary:

The M365 Licensing Specialist is our Subject Matter Expert on Microsoft licensing, responsible for both advisory guidance and operational execution across multiple channels and programs. You will guide our internal sales team and clients on the most appropriate licensing for given scenarios, process license orders and renewals, provision customer tenants, respond to licensing inquiries, and maintain accurate records and documentation.

This role requires deep familiarity with the Microsoft Cloud Solution Provider (CSP) program and an advanced ability to research and interpret Microsoft documentation including licensing guides, licensing terms, and other materials. Familiarity with meeting CMMC requirements with Microsoft GCC and GCC High licensing is a significant advantage.

As a Tier-1 Microsoft Direct Bill partner, we do not have distributor support for licensing questions—this role is our primary licensing expertise and operates with significant autonomy.

Key Responsibilities:

Licensing Advisory and Sales Support

• Serve as the internal subject matter expert on Microsoft licensing programs, SKUs, and terms
• Guide sales team on appropriate licensing for customer scenarios, including complex or high-value deals
• Advise clients on licensing options, optimization opportunities, and compliance alignment
• Interpret Microsoft licensing terms, agreements, and program rules
• Stay current on Microsoft program changes and communicate implications to internal teams
• Provide guidance on licensing/product feature strategies that support CMMC and other regulatory cybersecurity requirements

Research and Knowledge Management

• Research and interpret Microsoft documentation (MS Learn, License Agreements, Modern Work comparison resources, partner portals)
• Maintain and create internal licensing knowledge base and SOPs
• Document common Q&A and build internal FAQ resources
• Keep process documentation current as Microsoft programs evolve
• Track recurring internal questions to identify training gaps and documentation needs
• Contribute to process improvement initiatives

Licensing Operations

• Process new license orders and renewals across multiple channels: CSP Commercial, GCC, GCC High (VLC), Azure Government, and Azure EA
• Provision licenses through Microsoft Partner Center, including new customer tenants, Azure subscriptions, and license count adjustments
• Coordinate license renewal dates, service cutoffs, and cancellation windows
• Maintain monthly Microsoft license pricing downloads to support the sales team
• Track Microsoft licensing program updates that affect product availability, pricing, or program participation
• Communicate Microsoft policy changes and deadlines to internal teams
• Ensure the accuracy of required Microsoft program forms
• Maintain detailed records within ticket notes and emails
• Suspend customer Azure Government subscriptions when required by management
• Coordination and support on invoice generation and billing (with Billing & Accounting department)
• Coordination and support on pricing strategy (with Sales)

Customer Communication and Support

• Respond to client licensing inquiries
• Respond to internal colleague licensing questions (sales, delivery, and finance related)
• Send and confirm license activation communications to customers
• Instruct and follow up with customers about their procurement obligations (accepting Microsoft agreements)
• Resolve routine licensing requests such as license provisioning issues, access problems, and document re-sends
• Escalate technical issue