Microsoft Licensing Strategist – Cloud & On‑Prem Solutions

Heartland Business Systems

City of Pewaukee (WI)

On-site

USD 70,000 - 95,000

Full time

14 days+

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Job summary

Heartland Business Systems in Pewaukee, WI is seeking a Microsoft Licensing Specialist II – On Premise to drive software and services revenue through CSP licensing by engaging with prospects, customers, and internal sales teams.

You will analyze licensing requirements, create licensing scenarios aligned with business and technology needs, and explain cost, benefits and compliance. You’ll partner with finance, sales, and deployment teams to streamline licensing processes.

Qualifications

Bachelor’s Degree in Business or related field or equivalent work experience.
Proficient in Microsoft Office; working knowledge of Excel formulas and charting.
2+ years of experience communicating with business clients, independently or with a team.
Ability to prioritize and manage multiple tasks in a business setting.

Responsibilities

Maintain an intermediate understanding of on-premise licensing models (Open Volume, Perpetual CSP, Enterprise Agreement) and migrations to cloud licensing.
Act as customer-facing licensing specialist to analyze licensing requirements and provide guidance.
Create licensing scenarios aligned with client business, operational, and financial requirements.
Execute and sell licensing solutions, ensuring understanding of cost, benefits, and compliance.
Partner with finance, sales and other departments to improve licensing processes for Microsoft cloud and on-prem products.
Deliver services related to on-premise licensing including RV Tools analysis, renewal management, and procurement & analysis of licensing statements.
Present to individuals and small groups on Microsoft licensing and HBS’s value propositions.