VP, Compliance – Disability and Leave Operations

⁠​‌‌​​​‌​​​‌‌‌​‌​​​‌‌‌​​​​‌​​‌​‌‌​​‌‌‌​​‌⁠

JOB DESCRIPTION

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!

ABOUT US

Why Crawford?

Because a claim is more than a number - it’s a person, a child, a friend. It’s anyone who looks to Crawford on their worst days. And by helping to restore their lives, we are helping to restore our community - one claim at a time.

At Crawford, employees are empowered to grow, emboldened to act and inspired to innovate. Our industry-leading team pioneers new solutions for the industries and customers we serve. We’re looking for the next generation of leaders to take this journey with us.

We hail from more than 70 countries and speak dozens of languages, reflecting the global fabric of the audience we serve. Though our reach is vast, we proudly operate as One Crawford: united in purpose, vision and values. Learn more at www.crawco.com.

When you accept a job with Crawford, you become a part of the One Crawford family. And as part of the One Crawford family, we offer a comprehensive Total Rewards package to our employees to assist with their financial, health/wellness, continuing education/training and other needs:

• Competitive base pay

- The Pay Range/Salary represents the anticipated low and high pay that may be offered for this position. To determine the actual offer, Crawford considers a wide range of factors including the candidate’s previous experience and education, market rates, minimum pay requirements for the applicable jurisdiction, business segment, supply/demand, and scheduled hours.

• Bonus/Incentive Pay and other Performance-Based Rewards, if applicable.
• We offer a well-rounded benefits package that encourages wellness and helps our employees to be an educated healthcare consumer. The core benefits* offered include:

- Medical, Dental and Vision Plans
- Prescription Drugs
- HSA, HRA, and FSA Accounts
- Paid Holidays, Vacation and Sick Leave
- 401(k) Retirement Plan
- Tuition Assistance
- Paid Parental Leave
- Supplemental Health Benefits

Other Benefits currently available at no cost include: - Enhanced Mental Health Support
- Virtual Physical Therapy
- Caregiving Services
- Life Assistance Program

*The above information highlights some of the benefits currently available to eligible full-time employees.

• Training programs that promote continuous learning and career progression while enhancing job performance.
• Sustainability programs that give back to the communities in which we live and work.
• A culture of respect, collaboration, entrepreneurial spirit and inclusion.

Crawford & Company participates in E-Verify and is an Equal Opportunity Employer. M/F/D/V Crawford & Company is not accepting unsolicited assistance from search firms for this employment opportunity. All resumes submitted by search firms to any employee at Crawford via-email, the Internet or in any form and/or method without a valid written Statement of Work in place for this position from Crawford HR/Recruitment will be deemed the sole property of Crawford. No fee will be paid in the event the candidate is hired by Crawford as a result of the referral or through other means.

RESPONSIBILITIES

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.
  

QUALIFICATIONS

• 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