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Licensing Compliance Analyst
Chicago, ILApril 1st, 2026
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 our delivery team and building out the analytical backbone that supports every client engagement.Role DescriptionThis is a hands on licensing analysis role. You will be responsible for conducting software baselines, effective licence positions (ELPs), compliance assessments, and deployment analyses across multiple vendor estates. Your core vendors will be Microsoft, VMware (Broadcom), Autodesk, and Adobe. Experience with Oracle, IBM, SAP, or ServiceNow is a strong plus and will expand the engagements you work on.You will work alongside our senior consultants and founders, providing the detailed data work and analysis that underpins our advisory, negotiation, and audit defence engagements. This is not a strategy or sales role. It is the analytical engine room where accuracy, thoroughness, and speed directly drive client outcomes.Day to day, you will:Build and maintain software baselines and ELPs across Microsoft, VMware, Autodesk, and Adobe estatesCollect, normalise, and reconcile deployment data from client environments (SCCM, MECM, vCenter, Adobe Admin Console, Autodesk Account, and similar tools)Map deployed software against entitlements, contracts, and licence agreements to identify compliance gaps and optimisation opportunitiesProduce client ready reports that clearly present licensing positions, risks, and recommendationsSupport audit defence engagements by preparing detailed compliance documentation and counter positionsAssist with Vendor Shield subscriber quarterly reviews by maintaining up to date licensing positions across covered vendorsTrack vendor programme changes, metric updates, and licensing model shifts for your covered vendorsCollaborate with senior consultants on multi vendor engagements, contributing analysis across the full vendor estateQualifications3+ years of experience in software licensing analysis, software asset management (SAM), or licence complianceDemonstrated ability to build ELPs and software baselines for at least two of the following: Microsoft, VMware/Broadcom, Autodesk, AdobeHands on experience with deployment discovery tools (SCCM/MECM, vCenter, Snow, Flexera, ServiceNow SAM, or similar)Strong Excel and data manipulation skills. You will be working with large datasets dailyUnderstanding of common licensing models (per user, per device, per core, subscription, named user, concurrent)Detail oriented and methodical. Errors in baselines create real compliance risk for clientsComfortable working remotely and managing multiple concurrent deliverables with clear deadlinesGood written communication. You will need to explain technical findings in plain language for client audiencesExperience with Oracle, IBM, SAP, or ServiceNow licensing is a valuable plusSAM related certifications (CSAM, ITIL, or vendor specific) are welcome but not requiredWhat makes this role differentAt most SAM practices you run the same tool report on repeat. Here you are working on live advisory and negotiation engagements where your analysis directly shapes multi million dollar licensing decisions. You will see the commercial impact of your work, not just file reports into a queue. You are joining a small, high calibre team with direct access to the founders and senior consultants, and you will build deep expertise across multiple vendors rather than being siloed into one.
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