Microsoft Licensing Strategist: On-Prem to Cloud (CSP)

HEARTLAND-BUSINESS-SYSTEMS-LLC; Little Chute (WI); On-site; USD 70,000 - 95,000; Full time

Benefits offered by this job

Competitive compensation package

Growth opportunities

Personal development

Work life balance

Recognition and awards

Job summary

Heartland Business Systems in Wisconsin seeks a Microsoft Licensing Specialist II – On Premise to drive licensing revenue by advising prospects and customers on on-premise and CSP licensing options. You will analyze licensing scenarios, present cost and compliance details, and collaborate with finance, sales, and practice leaders to optimize licensing deployments across client environments.

Strong communication, strategic thinking, and the ability to manage multiple licensing projects are

Qualifications

• 2+ years of experience communicating with business clients.
• Ability to prioritize and manage multiple tasks in a business setting.
• Bachelor’s Degree in Business or related field, or equivalent work experience.
• Proficient in Outlook, Word, PowerPoint, Excel, Teams; working knowledge of Excel formulas and charts.
• Maintain an outcome-focused mindset and be a team player.

Responsibilities

• Analyze licensing requirements and advise clients on Microsoft licensing models.
• Create licensing scenarios aligned with client business strategy and technology needs.
• Execute licensing solutions and explain costs, benefits, and compliance.
• Collaborate with finance, sales, and other departments to streamline licensing processes.
• Present licensing concepts to individuals and groups across departments.
• Maintain understanding of CSP and on-prem vs cloud licensing changes and promotions.

Skills

Client communication

Prioritization

Team player

Professional attitude

Education

Bachelor's degree in Business or related field

Tools

Microsoft Outlook

Microsoft Word

Microsoft PowerPoint

Microsoft Excel

Microsoft Teams

Job description

Heartland Business Systems in Wisconsin seeks a Microsoft Licensing Specialist II – On Premise to drive licensing revenue by advising prospects and customers on on-premise and CSP licensing options. You will analyze licensing scenarios, present cost and compliance details, and collaborate with finance, sales, and practice leaders to optimize licensing deployments across client environments.

Strong communication, strategic thinking, and the ability to manage multiple licensing projects are