Licensing Specialist II – On Premise

Heartland Business Systems

Microsoft Licensing Specialist II driving software and services revenue in CSP licensing model. Engaging with clients to analyze requirements and drive compliance with Microsoft licensing.

Posted 7/17/2026full-timePewaukee • Wisconsin • 🇺🇸 United StatesJuniorMid-LevelWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in Microsoft Licensing models, including Open Volume, Perpetual CSP, and Enterprise Agreement, while effectively communicating licensing solutions to clients. Proficient in managing licensing scenarios that align with business requirements and ensuring compliance with Microsoft licensing standards.

Highest-signal resume keywords

Microsoft Licensing ProgramsCSP Licensing ModelInside Sales ExperienceData Presentation SkillsMicrosoft Office Proficiency

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Microsoft LicensingLicensing ComplianceRenewal ManagementLicense Agreement AnalysisMicrosoft Price ListsExcel FormulasData AnalysisProactive CampaigningLicensing Scenario CreationStakeholder Coordination

Soft Skills

Communication SkillsPrioritizationTeam CollaborationClient EngagementPresentation Skills

Tools & Technologies

Microsoft OutlookMicrosoft WordMicrosoft PowerPointMicrosoft ExcelMicrosoft Teams

Industry Keywords

Cloud Solution ProviderOn-Premise LicensingSoftware RevenueBusiness StrategyOperational Requirements

Tech Stack

Tools & technologies

Cloud

About the role

Key responsibilities & impact

The Microsoft Licensing Specialist II – On Premise is responsible for driving top line software and services revenue in Microsoft Cloud Solution Provider (CSP) licensing model by engagements with prospects, customers, and internal sales teams.
Maintain an intermediate understanding level of on-premise licensing model (including but not limited Open Volume, Perpetual CSP, Enterprise Agreement) and how it may translate to a migration to cloud licensing.
Act as customer-facing licensing specialist to analyze licensing requirements and provide guidance and support to clients regarding Microsoft licensing models, investments, and compliance.
Create licensing scenarios that align with client’s business strategic, operational, technology, and financial requirements.
Execute and sell customers on licensing solutions, ensuring they understand the cost, benefits, and compliance requirements.
Partner with HBS finance, sales and other departments to develop and/or improve or streamline the presales, transactional, and deployment processes of Microsoft cloud and on-prem products.
Deliver a variety of services related to on-premise licensing include RV Tools analysis, renewal management, proactive campaigning, license keys/license agreement attainment, procurement & analysis of Microsoft Licensing Statements.
Present to individuals and small groups of people across different business departments and roles on the topic of Microsoft licensing & HBS’s core value propositions.
Maintain a basic understanding of all aspects of the Microsoft Cloud Solution Provider (CSP) model including but not limited to price changes, policy changes, and promotions, as it pertains to recommending on-premises licensing.
Manage the lifecycle of Microsoft-funded engagements, including program administration, stakeholder coordination, and cross-functional alignment with marketing and practice leaders to maximize program utilization and business outcomes.

Requirements

What you’ll need

2+ years of experience (leading/initiating discussion, proactive) communicating directly with (business) clients, independently or alongside other teammates
Proven ability to prioritize and address multiple tasks at one time in a business setting
Bachelor’s Degree in Business or related field, or equivalent work experience
Proficient in Microsoft Outlook, Word, PowerPoint, Excel, Microsoft Teams; working knowledge of Excel formulas and charting or similar productivity tools
1+ years of network/technical computing experience (preferred)
1+ years of experience formally presenting data and prewritten PPT to clients (preferred)
1+ years of experience working with Microsoft price lists (CSP) (preferred)
2+ years of experience working with Microsoft price lists (EA, Open, OVS-ES) (preferred)
2+ years of experience working with Microsoft Licensing programs / agreements / products (preferred)
2+ years of experience in inside sales or sales support related to Microsoft products (preferred)

Benefits

Comp & perks

Equal Opportunity Employer – Including Disabled and Veterans