Microsoft Licensing Specialist

About Paragon Micro

Paragon Micro is a leading provider of IT solutions and services, helping organizations modernize, secure, and optimize their technology investments. For more than two decades, we have partnered with clients across commercial, public sector, healthcare, and enterprise markets to deliver innovative technology solutions backed by deep expertise and exceptional customer service.

At Paragon, our people are our greatest asset. We foster a collaborative, entrepreneurial culture where innovation, accountability, and customer success drive everything we do. Our team members are empowered to bring new ideas forward, develop their careers, and make a meaningful impact for both our customers and our organization.

About the Role

Paragon Micro is seeking an experienced and customer-focused Microsoft Licensing Specialist to join our Cloud & Orchestration team. This role serves as a trusted advisor and subject matter expert for Microsoft licensing programs, helping customers and internal teams navigate complex licensing requirements and identify solutions that align with business objectives.

The Microsoft Licensing Specialist will work closely with sales, operations, finance, technical resources, and customers to support licensing recommendations, quoting, renewals, subscription management, and ongoing licensing strategy. This individual will play a key role in ensuring licensing accuracy, optimizing customer outcomes, and delivering a best-in-class customer experience.

To support collaboration and business needs, we are targeting this position to be based on site at our Corporate Headquarters in Buffalo Grove, IL. Candidates must be able to work in-office on a regular basis. 

What You'll Do

• Serve as a subject matter expert for Microsoft licensing, with particular emphasis on Microsoft CSP licensing. 
• Advise internal teams and customers on Microsoft licensing options, requirements, and best practices. 
• Help determine the appropriate Microsoft licensing solutions based on customer requirements, environments, and business needs. 
• Support licensing for Microsoft cloud and software offerings, including products such as Microsoft 365, Azure, Dynamics 365, Power Platform, Windows, and related Microsoft solutions, as applicable. 
• Understand Microsoft subscription models, licensing terms, product use rights, and program requirements. 
• Assist with licensing quotes, configurations, renewals, subscription changes, and customer licensing inquiries. 
• Review customer environments and requirements to identify appropriate licensing approaches and potential optimization opportunities. 
• Help customers understand licensing changes, Microsoft program updates, and their potential business or financial impact. 
• Partner closely with sales, account management, operations, finance, technical teams, and other stakeholders to ensure licensing solutions are accurate and supportable. 
• Assist sales teams during customer conversations when deeper Microsoft licensing expertise is required. 
• Research and resolve complex Microsoft licensing questions and escalations. 
• Maintain current knowledge of Microsoft's evolving licensing programs, policies, pricing structures, and CSP requirements. 
• Help develop and maintain internal documentation, processes, tools, and best practices related to Microsoft licensing. 
• Contribute to improving licensing processes and customer experience within a small, highly collaborative team.

Who You Are

You are a licensing professional who enjoys solving complex challenges and helping customers maximize the value of their Microsoft investments. You combine technical licensing expertise with strong business acumen and exceptional attention to detail. You thrive in a collaborative environment, communicate effectively with both technical and non-technical audiences, and take pride in delivering accurate, customer-focused solutions.

You are naturally curious, continuously expanding your knowledge as Microsoft programs evolve, and you are comfortable serving as a trusted resource for customers, sales teams, and internal stakeholders.

• Bachelor's degree in Business, Information Technology, Finance, or a related field preferred; equivalent experience will be considered.
• 5+ years of experience supporting Microsoft licensing programs, cloud subscriptions, software asset management, or licensing operations.
• 3+ years of hands-on experience working with Microsoft Cloud Solution Provider (CSP) licensing.
• Demonstrated knowledge of Microsoft licensing programs, commercial licensing models, and subscription-based licensing solutions.
• Experience supporting Microsoft licensing quotes, renewals, subscription modifications, and customer licensing inquiries.
• Experience advising sales teams and customers on licensing options, requirements, and best practices.
• Experience interpreting Microsoft Product Terms, licensing documentation, and program requirements.
• Strong analytical and problem-solving skills with the ability to evaluate customer environments and recommend appropriate licensing solutions.
• Proven ability to manage multiple priorities and customer requests while maintaining a high level of accuracy.
• Advanced proficiency with Microsoft Excel and related business tools for data analysis, reporting, and reconciliation.
• Strong written and verbal communication skills, including the ability to explain complex licensing concepts to both technical and business audiences.
• Demonstrated ability to independently research, troubleshoot, and resolve complex licensing questions.
• Must be a U.S. citizen.

Preferred Qualifications

• 7+ years of Microsoft licensing experience within a Microsoft Partner, CSP provider, MSP, reseller, distributor, or technology solutions organization.
• Experience supporting Microsoft 365, Azure, Dynamics 365, Power Platform, Windows, and related Microsoft solutions.
• Experience managing licensing portfolios, renewals, or software subscription lifecycles across multiple customer accounts.
• Experience supporting customer licensing assessments, optimization reviews, and renewal planning activities.
• Familiarity with Microsoft Partner Center and distributor licensing platforms.
• Microsoft certifications such as MS-900, AZ-900, or other Microsoft cloud and licensing certifications.
• Experience supporting sales organizations through licensing consultations, customer presentations, and proposal development.

What Sets You Apart

• You are highly detail-oriented and understand that licensing accuracy directly impacts both customer success and business profitability.
• You possess a consultative mindset and focus on solving customer challenges rather than simply processing transactions.
• You are comfortable navigating ambiguity and adapting to Microsoft's continually evolving licensing programs and commercial models.
• You build trust through responsiveness, expertise, and a commitment to delivering exceptional customer experiences.
• You enjoy collaborating across departments and contributing to a high-performing team environment.

Why Join Paragon Micro

• Opportunity to work alongside industry-leading technology professionals.
• Collaborative and entrepreneurial culture where your contributions make a direct impact.
• Ongoing opportunities for professional development and career growth.
• Exposure to cutting-edge Microsoft technologies and cloud solutions.
• Ability to influence customer success and help organizations maximize their technology investments.