Director, Leave of Absence

Travelers • Hartford, CT

1d

About The Position

The Director, Leave of Absence leads the team responsible for administering Travelers' Leave of Absence (LOA) program, playing a primary role in setting the long-term vision and roadmap, owning vendor relationships, and building cross-functional partnerships that enable a compliant, efficient, and employee-centered leave experience. This role is critical in shaping how leave administration evolves with regulatory changes, business priorities, and emerging technology, including AI-driven innovation. A successful employee in this role combines compliance expertise with the ability to drive operational excellence, make data-driven decisions, and develop a high-performing team.

Requirements

• College degree in HR, business, or a related field.
• 7-10 years of experience in Operations, Customer Service and/or HR, preferably with some Leave of Absence-specific experience.
• Prior people leadership experience.
• Experience with AbsenceSoft or a comparable leave management platform.
• Expert analytical, problem solving, influencing, communications, leadership and project management skills.
• Thorough knowledge of general PC applications, including all aspects of MS Office Suite, HRIS systems and other HR software.
• Prior vendor management experience.
• Expert knowledge of at least one HR Operational function and a strong understanding of other HR Operational functions.
• Ability to work effectively with internal and external teams; ability to influence at all levels of the organization.
• Highly ethical and can maintain confidentiality.
• Strong understanding of the overall HR function and insurance industry.
• Five years of either human resources, customer service or operations experience.
• Three years of people leadership experience.

Responsibilities

• In partnership with team leadership, set the strategic vision and roadmap for the Leave of Absence Administration team, ensuring the function stays ahead of regulatory changes, evolving business priorities, and shifting employee experience expectations.
• Drive technology adoption and innovation for the LOA function, including AI, to automate processes, improve compliance accuracy, and enhance the employee experience through emerging tools.
• Own the end-to-end AbsenceSoft vendor relationship, including system governance, release accountability, and ongoing optimization in partnership with HR Technology.
• Partner with Benefits and Legal to establish standards for policy interpretation, new state leave implementation, and ensuring administration aligns with leave program design.
• Establish and maintain cross-functional alignment with the Contact Center, Payroll, and Benefits Administration leadership, defining shared SLAs, escalation protocols, and feedback loops focused on quality and employee experience.
• Monitor third-party administrator performance, escalating systemic vendor issues to the Benefits team; serve as the primary LOA point of contact for concerns beyond individual case resolution.
• Leverage analytics and program insights to develop and present data-driven recommendations for program improvements to senior leadership.
• Provide direct people leadership to a team of LOA employees, driving team culture, development, performance management, and the overall training strategy.
• Perform other duties as assigned.

Benefits

• Health Insurance
• 401(k) matching
• Pension Plan
• Paid Time Off
• Paid company Holidays
• Wellness Program
• Matching Gift and Volunteer Rewards program

What This Job Offers

• Job Type: Full-time
• Career Level: Director