VP, Compliance – Disability and Leave Operations

Vice President, Compliance - Disability & Leave Operations Remote - Anywhere in the U.S.

Are you a compliance and legal leader with expertise in FMLA, ADA, Disability, Leave Management, and Accommodation Programs? We're seeking a strategic executive to lead compliance governance, regulatory oversight, and enterprise-wide disability and leave operations.

✨ Key Responsibilities:

✅ Lead compliance programs for FMLA, ADA, STD, LTD, Paid Parental Leave, and State Leave Programs
✅ Translate complex regulations into scalable operational practices
✅ Provide executive guidance on regulatory risk, litigation exposure, and compliance strategy
✅ Partner with Operations, Legal, HR, Product, Quality, and Executive Leadership
✅ Drive compliant, consistent, and high-quality service delivery

Ideal Background:

✔ Extensive disability and leave compliance expertise
✔ Strong regulatory and legal interpretation skills
✔ Executive leadership experience in compliance, leave administration, or employee benefits
✔ JD preferred

Apply today or message me to learn more!


* Juris Doctor (JD) from an ABA-accredited law school required


* Active license to practice law in at least one U.S.

jurisdiction preferred.


* 12+ years of progressive responsible legal and regulatory compliance experience supporting disability, leave, accommodations, employment law, or labor law, including at least 5 years in executive leadership roles.


* Expert knowledge of FMLA, ADA/ADAAA, PWFA, Title VII, ERISA, HIPAA, state leave laws, workers' compensation intersections, disability benefits, and employment law.


* Experience providing legal counsel to executive leadership regarding regulatory compliance and operational risk.


* Experience leading responses to government investigations, litigation support, regulatory audits, and complex employment law matters.


* Experience working within corporate legal departments, law firms, insurance carriers, or third-party administrators supporting disability and leave programs.


* Proven experience leading audits, process reviews, regulatory risk assessments, and cross-functional implementation of compliance or operational change initiatives.


* Strong leadership, executive communication, analytical, and decision-making skills, with the ability to influence across functions and drive results through others.


* Background in large-scale leave operations, insurance, or third-party administration, with responsibility for leading teams or enterprise programs.


* Experience supporting technology-enabled leave or disability products and leading implementation efforts that improve compliance, efficiency, and scalability.


* Professional certifications such as CEBS, CPDM, FMLA/ADA certification, CRCM, or CCEP are preferred.

#LI-DV1

Strategic Regulatory Leadership & Governance


* Serve as the executive legal authority for disability, leave, and accommodation compliance, providing ...