Software Renewals & License Compliance Specialist Contractor

Description Great people. Greater business impact. About CAI CAI Software builds digital work execution platforms and software solutions that help manufacturing businesses operate with greater clarity and control. Our people bring structure to complexity by replacing fragmented, paper-based processes with connected digital workflows that improve visibility, compliance, and decision-making in real industrial environments. With 45+ years of experience and a presence across 10+ countries, CAI combines deep industry understanding with practical technology. Our team consists of ~800 employees worldwide who work across 15 core industries and support 5,000+ customers, guided by sound judgment, long-term thinking, and outcomes that endure. CAI Business Units and the Markets We Serve CAI Software is organized into three business units - Graphic Communications, Process Manufacturing, and Discrete Manufacturing – aligned to the markets we serve. This structure allows our teams to stay close to customer needs while operating with the scale and support of a global software company. This role is part of our Shared Services team which includes the functions that support CAI business units. This model enables deep industry focus at the BU level while benefiting from the scale, expertise, and stability of one unified organization—allowing CAI Software to deliver specialized solutions About the Role As a Software Renewals & License Compliance Specialist Contractor at CAI Software, you will be responsible for recovering revenue from past-due and lapsed software renewals while also identifying and pursuing software compliance opportunities across our customer base. This is a hybrid role that combines traditional renewal recovery with a compliance-driven approach to revenue protection. You will own the end-to-end process of re-engaging customers whose maintenance, term, or SaaS contracts expired without renewal—primarily focusing on accounts that lapsed in the prior fiscal year and were not actively pursued at the time of expiration. In parallel, you will collaborate closely with Sales and Customer Success to identify cases where customers may be over-deploying or under-licensed on CAI software, and drive those conversations toward compliant resolution and incremental revenue capture. This role requires a unique blend of tenacity, diplomacy, and analytical rigor. You will need to approach sensitive customer situations with professionalism—balancing the urgency of past-due recovery with a consultative approach that preserves long-term customer relationships. What You’ll Do Past-Due Renewal Recovery Own the recovery pipeline for lapsed and expired renewals, with a primary focus on contracts that went past due in the prior fiscal year Research account history, contract terms, and prior engagement activity to build an informed outreach strategy for each lapsed account Execute multi-channel outreach campaigns (phone, email, escalation) to re-engage customers and drive contract reinstatement or back-dated renewal agreements Negotiate renewal terms for lapsed contracts, including handling objections around gaps in coverage, retroactive pricing, and reinstatement fees Collaborate with Legal, Deals Desk, and Finance to structure recovery agreements that are commercially sound and executable Track and report on recovery pipeline status, conversion rates, and recovered ARR on a weekly basis Software Compliance & License Enforcement Partner with Sales and Customer Success to identify accounts where software usage exceeds licensed entitlements Analyze deployment data, license records, and usage reports to build compliance cases with clear, defensible documentation Lead compliance outreach conversations with customers, presenting findings professionally and guiding accounts toward compliant licensing and true-up agreements Develop and refine compliance playbooks, escalation workflows, and communication templates in partnership with leadership Coordinate with Legal on escalation strategy for non-responsive accounts or disputes related to compliance findings Track compliance pipeline opportunities and report on compliance-driven revenue contribution General Maintain accurate records of all customer interactions and pipeline activity in internal tracking systems Provide regular status updates and forecasts to Renewals leadership Cross-functionally collaborate with internal stakeholders to deliver competitive solutions and resolve complex account issues Contribute to the development of policies, processes, and best practices for the renewals and compliance function What We’re Looking For 3–5 years of experience in software renewals, license compliance, revenue recovery, or a related sales/account management function Demonstrated experience with software license compliance, audit processes, or entitlement management is strongly preferred Proven ability to engage with difficult or sensitive customer situations—including past-due collections and compliance conversations—with professionalism and persistence Strong communication, negotiation, and consultative selling skills Comfortable engaging C-level executives and senior IT stakeholders Analytical mindset with the ability to interpret deployment data, contract terms, and usage reports to build a business case Detail-oriented with excellent organizational and pipeline management abilities Experience in outbound phone-based sales, collections, or account recovery Proficiency in Microsoft Office; experience with NetSuite, Salesforce, or license management platforms is a plus Familiarity with software licensing models (perpetual, term, SaaS, maintenance) and entitlement structures Multilingual skills (Spanish, Italian, or French) are advantageous Preferred Background Prior experience at a software company in a compliance, audit, or asset management role Background working with ERP, MES, or industrial software environments Experience developing or executing compliance remediation campaigns Familiarity with contract law fundamentals as they relate to software licensing CAI Software is an “EEO/Veterans/Disabled employer.” Equal Employment Opportunity CAI Software is an Equal Opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, national origin, age, sex (including pregnancy, sexual orientation, and gender identity or expression), religion, disability, genetic information, marital status, veteran status, or any other basis protected by local, state or federal law. Disability Accommodation CAI Software endeavors to make reasonable accommodations for applicants with disabilities and disabled veterans pursuant to applicable federal and state law. If you are an individual with a disability and require a reasonable accommodation to complete any part of the application process or are limited in the ability or unable to access or use the online application process and need an alternative method for applying, please contact us at [email protected] or send an e-mail with your specific accommodation request. Work Authorization Applicants must be authorized to work in the United States. CAI Software does not unlawfully discriminate on the basis of citizenship or immigration status in accordance with the Immigration Reform and Control Act of 1986 (IRCA). Pay Transparency Nondiscrimination CAI Software will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information. 41 CFR 60-1.35(c).