Software Renewals & License Compliance Specialist Contractor

CAI World-Wide•Salt Lake, UT

8d•Hybrid

About The Position

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.

Requirements

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
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).

Nice To Haves

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

Responsibilities

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
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
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