Software Renewals & License Compliance Specialist Contractor

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 5000 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 ourShared Servicesteam 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 organizationallowing 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 renewalprimarily focusing on accounts that lapsed in the prior fiscal year and were not actively pursued at the time of 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 professionalismbalancing the urgency of past-due recovery with a consultative approach that preserves long-term customer relationships.

What Youll 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 Were Looking For

• 35 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 situationsincluding past-due collections and compliance conversationswith 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 Softwareis 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 Softwareendeavors 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 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 Softwarewill 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 contractors legal duty to furnish information. 41 CFR 60-1.35(c).

Required Experience:

IC