Senior Microsoft Licensing Consultant

Redress Compliance is an independent software licensing and cloud advisory firm. We help global enterprises reduce costs, mitigate compliance risks, and negotiate better outcomes with vendors including Oracle, Microsoft, IBM, SAP, Salesforce, ServiceNow, and Workday. We are Gartner recommended, vendor independent, and have delivered 500+ client engagements across North America, EMEA, APAC, and Latin America. We are scaling fast and building out our in house delivery capability across all major vendors.

Role Description

This is our first in house Microsoft specialist hire. You will lead client engagements across the full Microsoft licensing estate, including Enterprise Agreements, Microsoft 365, Azure, Copilot, and Server/CAL. You will work directly with the founders to deliver advisory, negotiation support, and compliance analysis for enterprise clients with Microsoft spend ranging from $2M to $50M+.

Today we subcontract Microsoft work at an 80/20 split. This hire brings delivery in house and is one of the highest impact moves on our margin roadmap. You will own the Microsoft practice and help us build it into a core revenue line alongside Oracle.

Day to day, you will:

• Lead Microsoft EA and SCE renewal negotiations on behalf of enterprise clients
• Conduct licensing position assessments across Microsoft 365, Azure, Dynamics, and Server/CAL environments
• Advise clients on cost optimisation strategies including licence harvesting, subscription right sizing, and Azure commitment planning
• Deliver compliance risk assessments and audit defence support for Microsoft engagements
• Support Vendor Shield subscription clients with ongoing Microsoft advisory as part of their quarterly reviews
• Brief clients on Microsoft programme changes, pricing shifts, and licensing policy updates
• Collaborate with the founders and other vendor specialists (Oracle, SAP, IBM) on multi vendor engagements
• Contribute to thought leadership content (articles, webinars, client briefings) to build the Redress Microsoft brand

Qualifications

• 7+ years of hands on experience in Microsoft enterprise licensing (EA, SCE, CSP, MPSA, or equivalent)
• Deep knowledge of Microsoft 365, Azure, Dynamics 365, and Server/CAL licensing models
• Direct experience negotiating Microsoft Enterprise Agreements or Cloud Solution renewals with Microsoft or through LSPs
• Ability to conduct independent licensing assessments and produce client ready deliverables
• Familiarity with Microsoft compliance and audit processes
• Strong commercial instincts. You understand how licensing decisions connect to cost, risk, and vendor strategy
• Comfortable working remotely and managing multiple concurrent client engagements
• Excellent written and verbal communication skills. You will be client facing from day one
• Experience at a licensing advisory firm, SAM practice, or vendor side licensing team is strongly preferred

What makes this role different

You are not joining a large consultancy where you will be one of fifty Microsoft people. You are the Microsoft practice. You will have direct client relationships, work alongside the founders, and shape how we deliver Microsoft advisory at scale. We are building toward a significant exit within 24 months and this role is a key part of the growth engine. Compensation reflects the seniority and impact of the role.