Director, Leave of Absence

Posted Yesterday
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Hartford, CT, USA
In-Office
120K-199K Annually
Senior level
Insurance
The Role
Lead and run the Leave of Absence administration team, own vendor and AbsenceSoft relationship, set strategic roadmap, drive technology and AI adoption, ensure regulatory compliance, partner with Benefits/Legal/Payroll/Contact Center, use analytics to improve the program, and provide people leadership and training for a high-performing LOA team.
Summary Generated by Built In
Who Are We?

Taking care of our customers, our communities and each other. That’s the Travelers Promise. By honoring this commitment, we have maintained our reputation as one of the best property casualty insurers in the industry for over 170 years. Join us to discover a culture that is rooted in innovation and thrives on collaboration. Imagine loving what you do and where you do it.

Job Category
Human Resources

Compensation Overview

The annual base salary range provided for this position is a nationwide market range and represents a broad range of salaries for this role across the country. The actual salary for this position will be determined by a number of factors, including the scope, complexity and location of the role; the skills, education, training, credentials and experience of the candidate; and other conditions of employment. As part of our comprehensive compensation and benefits program, employees are also eligible for performance-based cash incentive awards.

Salary Range$120,400.00 - $198,700.00

Target Openings
1

What Is the Opportunity?
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.What Will You Do?
  • 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.
What Will Our Ideal Candidate Have?
  • 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.
What is a Must Have?
  • Five years of either human resources, customer service or operations experience.
  • Three years of people leadership experience.
What Is in It for You?
  • Health Insurance: Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
  • Retirement: Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
  • Paid Time Off: Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
  • Wellness Program: The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
  • Volunteer Encouragement: We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.
Employment Practices

Travelers is an equal opportunity employer. We value the unique abilities and talents each individual brings to our organization and recognize that we benefit in numerous ways from our differences. 

In accordance with local law, candidates seeking employment in Colorado are not required to disclose dates of attendance at or graduation from educational institutions.

If you are a candidate and have specific questions regarding the physical requirements of this role, please send us an email so we may assist you.

Travelers reserves the right to fill this position at a level above or below the level included in this posting.

To learn more about our comprehensive benefit programs please visit http://careers.travelers.com/life-at-travelers/benefits/.

Skills Required

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

Travelers Compensation & Benefits Highlights

The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Travelers and has not been reviewed or approved by Travelers.

  • Retirement Support Feedback suggests total rewards are bolstered by a 401(k) match, a company‑funded pension, and a program that contributes to retirement savings when employees make student‑loan payments. These elements are consistently portrayed as standout strengths of the package.
  • Leave & Time Off Breadth Feedback suggests time off is generous from the start, with substantial PTO, paid holidays, and the option to purchase additional days. Defined leaves such as short‑term disability and bereavement further enhance perceived flexibility.
  • Healthcare Strength Feedback suggests medical, dental, and vision coverage is comprehensive, with multiple plan choices, HSAs/FSAs, and robust mental‑health and wellness resources. Day‑one eligibility and added programs like caregiver support and specialty care navigation reinforce depth.

Travelers Insights

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The Company
HQ: New York, NY
35,118 Employees

What We Do

Travelers provides insurance coverage to protect the things that are important to you – your home, your car, your valuables and your business. We have been around for more than 165 years and have earned a reputation as one of the best property casualty insurers in the industry because we take care of our customers, agents, brokers, communities and each other. Every day, our approximately 30,000 employees and 13,500 independent agents and brokers in the United States, Canada, the United Kingdom and Ireland help provide peace of mind to our customers. Our expertise and focus on innovation have made us an industry leader and the only property casualty company in the Dow Jones Industrial Average. Our history of advancements has propelled our company, and our industry, to deliver higher standards – from writing the first auto and space travel policies to founding the Travelers Institute for public policy and launching a hybrid car discount. By minimizing risk, preventing loss and helping our customers prepare for the unknown, Travelers’ comprehensive products and services enable individuals and businesses to feel confident and secure about the future.

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