Microsoft 365 & Azure Licensing Specialist (CSP/GCC/GCC High)

Agile IT • San Diego, CA

21h • 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. 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. 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. Why This Role? This is a builder's role with autonomy. If you're energized by deploying solutions, scripting away inefficiencies, and knowing your work helps defense contractors and government agencies operate securely—you'll fit right in. You'll work with cutting-edge Microsoft security technologies, develop deep expertise in GCC High and CMMC compliance, and have the latitude to shape how we deliver. We value people who make things better, not just people who complete tasks.

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 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

What This Job Offers

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