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

Company Description:NOTE: This is a business operations and product advisory role, not a technical engineering 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 ServicesProfessional 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 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. Key Responsibilities: Licensing Advisory and Sales SupportServe as the internal and client-facing subject matter expert on Microsoft licensing programs, SKUs, and termsGuide sales team on appropriate licensing for customer scenarios, including complex or high-value dealsAdvise clients on licensing options, optimization opportunities, and compliance alignmentInterpret Microsoft licensing terms, agreements, and program rulesStay current on Microsoft program changes and communicate implications to internal teamsProvide guidance on licensing/product feature strategies that support CMMC and other regulatory cybersecurity requirements Research and Knowledge ManagementResearch and interpret Microsoft documentation (MS Learn, License Agreements, Modern Work comparison resources, partner portals)Maintain and create internal licensing knowledge base and SOPsDocument common Q&A and build internal FAQ resourcesKeep process documentation current as Microsoft programs evolveTrack recurring internal questions to identify training gaps and documentation needsContribute to process improvement initiatives Licensing OperationsProcess new license orders and renewals across multiple channels: CSP Commercial, GCC, GCC High (VLC), Azure Government, and Azure EAProvision licenses through Microsoft Partner Center, including new customer tenants, Azure subscriptions, and license count adjustmentsCoordinate license renewal dates, service cutoffs, and cancellation windowsMaintain monthly Microsoft license pricing downloads to support the sales teamTrack Microsoft licensing program updates that affect product availability, pricing, or program participationCommunicate Microsoft policy changes and deadlines to internal teamsEnsure the accuracy of required Microsoft program formsMaintain detailed records within ticket notes and emailsSuspend customer Azure Government subscriptions when required by managementCoordination and support on invoice generation and billing (with Billing & Accounting department)Coordination and support on pricing strategy (with Sales) Customer Communication and SupportRespond to client licensing inquiriesRespond to internal colleague licensing questions (sales, delivery, and finance related)Send and confirm license activation communications to customersInstruct 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-sendsEscalate technical issues to internal engineering resources or open support tickets with Microsoft on customers' behalfMonitor and manage the licensing ticket queue in Autotask PSA (chiefly inbound customer inquiries and license related support requests)  How Success is Measured: Advisory EffectivenessSales team and client satisfaction with licensing supportAccuracy of licensing recommendations and program knowledgeTimeliness and quality of Microsoft program change communicationsKnowledge base & SOP contributions and documentation quality Operational ExcellenceOrder and provisioning accuracyTicket response timeFirst-contact resolution rateQualifications:Required Qualifications5+ years of experience with common Microsoft licensing programs (MOLP, MCA, EA, CSP, NCE, AOS-G, etc.)Working knowledge of Microsoft Partner CenterUnderstanding of Microsoft 365 and Azure licensing models, SKUs, and subscription typesAbility to research and interpret Microsoft licensing documentationStrong attention to detail and accuracyStrong discernment and reasoning skillsExcellent written and verbal communication skillsExperience with ticketing systems and customer support workflowsComfortable working in a remote environment Preferred QualificationsExperience with Microsoft Tier-1 direct-sell partner programsAOS-G (Agreement for Online Services for Government) experienceGCC and GCC High licensing experienceExperience with Volume Licensing Center (VLC)Experience with Azure Enterprise Agreement (EA) programsFamiliarity with CMMC compliance requirements is a significant advantage, and further education will be provided on the job.Experience with Autotask PSAExperience working at a Microsoft partnerAdditional Information:Compensation & BenefitsCompetitive salaryComprehensive benefits (medical, dental, vision, retirement, PTO, professional development)Fully remote work environment with flexibility and autonomyMission-driven work that directly strengthens our national security posture  

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