> Markdown version of [/jobs/ext/2735377-microsoft-licensing-specialist-ii](https://www.wearedevelopers.com/jobs/ext/2735377-microsoft-licensing-specialist-ii). Every page supports `.md` or `Accept: text/markdown`. Links point to the HTML versions so they work for humans too. Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md).

---

# Microsoft Licensing Specialist II

- **Company:** Heartland Technology Group Inc.
- **Location:** Brookfield, WI, United States
- **Experience:** Experienced
- **Salary:** $52,000.0 - $66,560.0
- **Contract:** Permanent contract
- **Skills:** Microsoft Word, Microsoft Excel, Microsoft Online Services, Microsoft Outlook, Microsoft PowerPoint, Productivity Software
- **Published:** September 5, 2026
- **Apply:** https://www.jofdav.com/jobs/59580280-microsoft-licensing-specialist-ii

## About the Role

* 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
 * Maintain an outcome focused mindset
 * Have strong prioritization skills
 * Always be a team player
 * Carry a professional attitude and respectful demeanor

## Description

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. This position directly contributes to the organization's annual Microsoft licensing growing revenue goals.

Roles and Responsibilities:

 * 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. *Heartland is an Affirmative Action/Equal Opportunity Employer of Minorities, Women, Protected Veterans and Persons with Disabilities.*


## Related Videos

- [Claude, MCP and n8n, or: How to Automate Your Day with AI-powered Workflows](https://www.wearedevelopers.com/videos/2043-claude-mcp-and-n8n-or-how-to-automate-your-day-with-ai-powered-workflows)
- [In-depth .NET Azure Functions: Isolated mode, performance and durable AI agents](https://www.wearedevelopers.com/videos/100207-in-depth-net-azure-functions-isolated-mode-performance-and-durable-ai-agents)
- [Developing the Rich Text Editor for DeepL.com](https://www.wearedevelopers.com/videos/1172-developing-the-rich-text-editor-for-deepl-com)
- [You’re a great coder? That alone won’t get you far: The soft skills secret in IT success](https://www.wearedevelopers.com/videos/1076-you-re-a-great-coder-that-alone-won-t-get-you-far-the-soft-skills-secret-in-it-success)
- [From Syntax to Singularity: AI’s Impact on Developer Roles](https://www.wearedevelopers.com/videos/900-from-syntax-to-singularity-ai-s-impact-on-developer-roles)
- [TOPsharing – Empowerment for Leadership Positions](https://www.wearedevelopers.com/videos/864-topsharing-empowerment-for-leadership-positions)

## Related Articles

- [What’s the Difference between a Junior, Mid, and Senior Developer?](https://www.wearedevelopers.com/magazine/238-what-s-the-difference-between-a-junior-mid-and-senior-developer)
- [UK Business Culture and Etiquette](https://www.wearedevelopers.com/magazine/326-uk-business-culture-and-etiquette)
- [Why Upskilling And Reskilling is Important For Developers](https://www.wearedevelopers.com/magazine/428-why-upskilling-and-reskilling-is-important-for-developers)
- [Is Software Engineering Over-Saturated?](https://www.wearedevelopers.com/magazine/418-is-software-engineering-over-saturated)
- [The Most Popular IT Jobs on the Market](https://www.wearedevelopers.com/magazine/376-the-most-popular-it-jobs-on-the-market)
- [System change: restart as developer?](https://www.wearedevelopers.com/magazine/39-system-change-restart-as-developer)