Microsoft 365 Licensing Advisor | Customer-Facing SME | GCC High, Azure, CSP | 100% Remote

NOTE: This is a customer-facing Microsoft licensing 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 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 Microsoft Licensing Advisor is our customer-facing Subject Matter Expert on Microsoft 365 and Azure licensing. You will consult with customers and internal colleagues on the right licensing for detailed, real-world scenarios—translating complex Microsoft product options into clear recommendations that align with business needs, compliance requirements, and budget.

This is a customer-facing licensing advisory role, not a technical engineering position. Your focus is on understanding customer needs, researching licensing options, and providing expert recommendations. You will manage customer requests through our ticketing system—updating tickets, responding to customers, and tracking conversations through resolution.

Success requires deep knowledge of Microsoft 365 and Azure products, features, and licensing models—and the ability to research and interpret Microsoft documentation to answer questions that don't have obvious answers. You must be comfortable engaging directly with customers and colleagues to understand their requirements and explain licensing options in plain terms.

Key Responsibilities

Customer and Internal Advisory (Primary Focus)

• Serve as the go-to expert for Microsoft licensing questions from customers and internal colleagues

• Consult with customers on the right licensing for their specific scenarios-- considering business requirements, compliance needs, budget, and technical constraints

• Guide the sales team on appropriate licensing for customer opportunities, including complex or high-value deals

• Advise on licensing options, optimization opportunities, and compliance alignment (especially CMMC)

• Interpret Microsoft licensing terms, product capabilities, and program rules for customers and colleagues

• Translate complex licensing information into clear, actionable recommendations

• Escalate technical implementation questions to engineering; this role advises on licensing, not technical configuration

Customer Communication via Tickets

• Monitor and manage tickets received from customers on licensing topics (Autotask PSA)

• Respond to customer licensing inquiries through the ticketing system

• Update ticket notes with research findings, recommendations, and next steps

• Manage ticket status to reflect the current stage of each conversation

• Track tickets through resolution; follow up with customers as needed

• Escalate complex or unresolved issues to the Licensing Program Manager or an internal Engineering resource

• Maintain response time SLAs and ensure customers receive timely, accurate information

Research and Knowledge Management

• Research and interpret Microsoft documentation (MS Learn, License Agreements, Modern Work comparisons, partner portals, CMMC compliance placemat, etc) to answer licensing questions

• Stay current on Microsoft product changes, new SKUs, and licensing program updates

• Document common Q&A and build internal FAQ resources

• Maintain and create internal licensing knowledge base articles and SOPs

• Track recurring questions to identify training gaps and documentation needs

Licensing Operations (Backup)

• Process license orders and renewals across CSP Commercial, GCC, GCC High (VLC), and Azure programs as needed

• Coordinate with Billing & Accounting on invoice timing for orders processed; create invoices or quotes as needed

What This Role Does Not Include

• Technical troubleshooting, system configuration, or hands-on IT work

• Azure architecture, deployment, or consumption optimization

• Microsoft 365 administration or technical support

Required Qualifications

• 3+ years of experience with Microsoft 365 and/or Azure licensing

• Deep knowledge of Microsoft 365 products, features, and licensing models

• Strong attention to detail and accuracy

• Ability to research and interpret Microsoft licensing documentation

• Experience advising customers or internal stakeholders on licensing decisions

• Excellent written and verbal communication skills

• Experience with ticketing systems and managing customer requests

• Comfortable working in a remote environment

• Self-motivated

Preferred Qualifications

• Experience with GCC and GCC High licensing

• Experience with Microsoft CSP, EA, or AOS-G programs

• Working knowledge of Microsoft Partner Center

• Familiarity with CMMC compliance requirements

• Experience with Autotask PSA or similar ticketing systems

Compensation & 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