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

Agile IT•San Diego, CA

5d•Remote

About The Position

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. 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 is a business operations and product advisory role, not a technical engineering position. You will not configure systems, troubleshoot technical issues, or perform hands-on IT work. Success in this role requires business acumen and attention to detail, along with the ability to investigate and interpret complex licensing terms, agreements, and program rules. This role requires deep familiarity with Microsoft 365 product licensing and features and an advanced ability to research and interpret Microsoft documentation including licensing documents, product comparisons, pricelists, 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.

Requirements

5+ years of experience with common Microsoft licensing programs (MOLP, MCA, EA, CSP, NCE, AOS-G, etc.)
Working knowledge of Microsoft Partner Center
Understanding of Microsoft 365 and Azure licensing models, SKUs, and subscription types
Ability to research and interpret Microsoft licensing documentation
Strong attention to detail and accuracy
Strong discernment and reasoning skills
Excellent written and verbal communication skills
Experience with ticketing systems and customer support workflows
Comfortable working in a remote environment

Nice To Haves

Experience with Microsoft Tier-1 direct-sell partner programs
AOS-G (Agreement for Online Services for Government) experience
GCC and GCC High licensing experience
Experience with Volume Licensing Center (VLC)
Experience with Azure Enterprise Agreement (EA) programs
Familiarity with CMMC compliance requirements is a significant advantage, and further education will be provided on the job.
Experience with Autotask PSA
Experience working at a Microsoft partner

Responsibilities

Licensing Advisory and Sales Support
Serve as the internal and client-facing 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 issues to internal engineering resources or open support tickets with Microsoft on customers' behalf
Monitor and manage the licensing ticket queue in Autotask PSA (chiefly inbound customer inquiries and license related support requests)

Benefits

Competitive salary
Comprehensive benefits (medical, dental, vision, retirement, PTO, professional development)
Fully remote work environment with flexibility and autonomy
Mission-driven work that directly strengthens our national security posture

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