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 legal interpretation and strategic counsel to executive leadership regarding federal, state, and local employment laws.
• Direct enterprise legal compliance strategy related to disability and leave operations, ensuring alignment with evolving legislation, regulatory guidance, judicial decisions, and client contractual obligations.
• Lead the organization's legal response to regulatory inquiries, agency investigations, subpoenas, audits, and significant compliance matters involving leave and accommodation programs.
• Advise executive leadership regarding legal risk exposure and recommend enterprise mitigation strategies.
• Lead the strategic interpretation, governance, and operationalization of laws and programs including FMLA, ADAAA, state PFML programs, workers' compensation intersections, ERISA, and employer-specific leave plans.
• Serve as the senior compliance advisor to operational and executive leaders on regulatory developments and their impact on policy, process, systems, client commitments, and business strategy.
• Establish and continuously enhance the compliance governance framework for disability and leave operations, including program standards, decision controls, escalation pathways, and enterprise risk monitoring.

Program Implementation, Policy & Process Management

• Direct the legal review, approval, implementation, and governance of compliance programs, policies, and SOPs related to leave, accommodations, return-to-work, and disability benefit administration.
• Lead cross-functional execution of regulatory and client-driven changes, ensuring documentation, workflows, controls, and operational playbooks are effectively implemented and sustained.
• Partner with Learning & Development and operational leaders to embed policy changes into training, job aids, readiness plans, and performance expectations for front-line teams and leaders.
• Provide legal oversight for enterprise policy development and ensure operational practices remain legally defensible and aligned with regulatory requirements.
  
  Risk Management & Quality Assurance
  
• Lead enterprise compliance risk assessments across the disability and leave ecosystem, identifying control gaps, emerging risks, and opportunities to strengthen operational integrity.
• Oversee compliance audits, quality reviews, and monitoring programs, including FMLA timeliness, ADA interactive process adherence, documentation standards, and claim decision accuracy.
• Direct investigation and resolution of escalations, audit findings, complaints, and potential violations; assign accountability and drive corrective and preventive actions to closure.
• Provide executive oversight for enterprise legal risk assessments, identifying emerging regulatory exposure and recommending mitigation strategies to executive leadership.
• Lead legal review of high-risk claims, precedent-setting decisions, regulatory complaints, class action risks, and complex accommodation matters.
• Partner with Corporate Legal regarding litigation strategy, discovery support, expert testimony preparation, and regulatory defense activities.

Leadership & Team Development

• Provide executive leadership, strategic direction, and organizational oversight for compliance professionals and/or cross-functional teams responsible for program delivery, monitoring, and implementation.
• Set priorities, establish performance expectations, and build team capability to support a high-performing, consultative compliance function.
• Foster a culture of accountability, continuous improvement, and operational excellence across compliance programs and partnerships.
• Build organizational legal compliance capabilities through executive coaching, succession planning, and enterprise talent development.

Training & Education

• Sponsor enterprise legal compliance education regarding FMLA, ADA, PWFA, Pregnant Workers Fairness Act, state leave regulations, ERISA, HIPAA, and evolving employment law requirements.
• Provide strategic guidance to leaders on emerging regulatory trends, implementation priorities, and operational impacts to ensure readiness and consistent execution.
• Act as the senior subject matter expert for complex, high-risk, or ambiguous cases requiring advanced regulatory interpretation and executive visibility

Monitoring, Reporting & Documentation

• Oversee compliance dashboards, regulatory trackers, audit results, and program performance reporting for internal and external stakeholders.
• Prepare and present executive-level reporting on trends, root causes, risk exposure, audit outcomes, and strategic recommendations.
• Monitor adherence to service-level expectations, regulatory timeframes, and program outcomes, and drive action plans to improve compliance and operational performance.
• Present enterprise compliance risk, legal exposure, litigation trends, regulatory developments, and strategic recommendations to executive leadership and governance committees.

Cross-Functional Collaboration

• Lead strategic collaboration with Legal, HR, Executive Leadership, Compliance, Operations, Quality, Product, and Client Services regarding enterprise leave and disability compliance.
• Lead or sponsor cross-functional initiatives with IT and product teams to implement compliant workflows, strengthen controls, and improve data integrity and user experience.
• Represent the organization in client meetings, regulatory examinations, legal proceedings, audits, governmental investigations, and strategic negotiations related to disability and leave compliance.