Microsoft Licensing Specialist II – On Premise

Heartland Business Systems; Little Chute (WI); On-site; USD 70,000 - 100,000; Full time

Job summary

Heartland Business Systems is seeking a Microsoft Licensing Specialist II – On Premise to drive licensing solutions for clients. You will analyze licensing requirements, present tailored scenarios, and collaborate with internal teams to optimize licensing processes and renewals.

The role focuses on on-premise licensing with exposure to CSP models, Open Volume, and EA programs, supporting both sales and deployment activities.

Qualifications

• Bachelor’s Degree in Business or related field.
• 2+ years of experience communicating with clients, independently or with teammates.
• Proficient in Microsoft Outlook, Word, PowerPoint, Excel; working knowledge of Excel formulas/charts.

Responsibilities

• Maintain an intermediate understanding of on-premise licensing models and how they translate to cloud licensing.
• Act as customer-facing licensing specialist to analyze licensing requirements and guide clients.
• Create licensing scenarios aligning with client business, operations, technology, and finance.
• Execute and sell licensing solutions, explaining cost, benefits, and compliance.
• Collaborate with finance, sales, and other departments to improve licensing processes.
• Deliver services related to on-premise licensing including RV Tools analysis, renewal management, and procurement.

Skills

Active Listening

Adaptability

Ambition

Assertiveness

Coaching and Development

Conflict Resolution

Customer Oriented

Decision Making

Goal Oriented

Presentation Skills

Relationship Building

Education

Bachelor’s Degree in Business or related field

Tools

Microsoft Office

Job description

Position Summary

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.

Job Type

Full-time

Roles and Responsibilities

• Maintain an intermediate understanding level of on-premise licensing model (including but not limited to 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 including 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 and 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

Competencies

• Active Listening – Ability to actively attend to, convey, and understand the comments and questions of others.
• Adaptability – Ability to adapt to change in the workplace - Ability to accept responsibility and account for his/her actions.
• Ambition – The drive to achieve personal advancement.
• Assertiveness – Ability to act in a self-confident manner to facilitate completion of a work assignment or to defend a position or idea.
• Coaching and Development – Ability to provide guidance and feedback to help others strengthen specific knowledge/skill areas.
• Conflict Resolution – Ability to deal with others in an antagonistic situation.
• Customer Oriented – Ability to take care of the customers’ needs while following company policy.
• Decision Making – Ability to make critical decisions while following company procedures.
• Goal Oriented – Ability to focus on a goal and obtain a pre‑determined result.
• Honesty / Integrity – Ability to be truthful and be seen as credible in the workplace.
• Innovative – Ability to look beyond the standard solutions.
• Leadership – Ability to influence others to perform their jobs effectively and to be responsible for making decisions.
• Motivation – Ability to inspire oneself and others to reach a goal and perform to the best of their ability.
• Presentation Skills – Ability to effectively present information publicly.
• Relationship Building – Ability to effectively build relationships with customers and co‑workers.

Required Experience

• 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.

Preferred Experience

• 1+ years of network/technical computing experience.
• 1+ years of experience formally presenting data and prewritten PPT to clients.
• 1+ years of experience working with Microsoft price lists (CSP).
• 2+ years of experience working with Microsoft price lists (EA, Open, OVS‑ES).
• 2+ years of experience working with Microsoft Licensing programs / agreements / products.
• 2+ years of experience in inside sales or sales support related to Microsoft products.

Required Skills, Education and/ or Certifications

• 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.

Preferred Skills, Education and/ or Certifications

• Proven experience operating with a high-level of organization and follow through.
• MS‑900: Microsoft 365 Fundamentals.
• AZ‑900: Azure Fundamentals.

Equal Opportunity Employer – Including Disabled and Veterans