Director, Benefits and Leave

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District of Columbia Public Schools (DCPS) provided pay range

This range is provided by District of Columbia Public Schools (DCPS). Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$115,320.00/yr - $130,146.00/yr

Position Overview

The Office of Employee Services (OES) is dedicated to enhancing student success by attracting, hiring, and retaining top talent in DC Public Schools. By providing exceptional employee services support to our DCPS team members from recruitment to retirement, we aim to empower our employees to focus on what matters most—our students. With a focus on people-centered support and operational excellence, we leverage talent with a goal of all students being supported by staff who feel valued. OES is comprised of the following teams:

• The Compensation and Retirement team is responsible for ensuring that DCPS administers compensation policies consistently and in accordance with applicable legislation and collective bargaining agreements. The team also provides support to departments during reorganizations, reductions in force (RIFs), and other personnel action such as hiring, transfers, promotions and demotions. Additionally, they offer counseling, guidance, and strategic planning for employee retirement.
• The Benefits and Leave team is responsible for administering employee benefits and managing leave of absence (LOA) and Family and Medical Leave Act (FMLA) processes. This team also oversees the agency's health, life, tax-sheltered annuity, flexible spending, and supplemental benefits programs.
• The HR Information Systems and Records Management team ensures systems data integrity, manages the data reporting function, processes personnel actions in PeopleSoft, provides position management support for schools and Central Services, provides time and labor support, and manages the personnel filing system for all DCPS employees. The team also serves as a key HR partner to external agencies like the Office of the Chief Technology Officer (OCTO), the DC Office of Human Resources (DCHR), and the Office of Pay and Retirement Services (OPRS).
• The Employee Experience (EE) team provides all new employees with robust onboarding support and leads the development and implementation of resources, workshops, and events designed to support employee needs. EE also supports procedural compliance related to background clearance checks for DCPS employees and manages additional support functions including the Employee Services helpline, walk-in visitor reception, and employee offboarding processes.
• The Strategic Staffing team is responsible for hiring for all positions in DCPS. The team provides budgeting support, works with principals and supervisors to develop their staffing plans and personnel budgets, and works with employees, principals, and hiring managers on staffing changes.
• The Instructional Talent Acquisition and Retention division is responsible for the recruitment, selection, and retention efforts for educational aides, related service providers, instructional coaches, and teachers. This work includes nationwide recruitment to ensure that DCPS has excellent educators who are able to serve the diverse needs of our students.

The Director of Benefits and Leave leads the Benefits and Leave team and is responsible for the strategic leadership and operational management of all employee benefits and leave programs within DC Public Schools (DCPS). This role ensures compliance with applicable laws and policies and drives continuous improvement in service delivery in the areas of benefits and leave of absence. The Director also serves as a key liaison with internal and external stakeholders and plays a critical role in aligning benefits and leave operations with broader organizational goals.

The Director, Benefits and Leave will report to the Deputy Chief, HR Operations .

Essential Duties and Responsibilities

The below statements are intended to describe the general nature and scope of work being performed by this position. This is not a complete listing of all responsibilities, duties, and/or skills required. Other duties may be assigned.

Strategic Leadership & Team Management

• Leads the development and execution of benefits and leave strategies aligned with DCPS priorities.
• Establish and uphold high standards for customer service by guiding staff toward excellence through training, support, and clear expectations, while consistently monitoring performance and holding team members accountable to ensure service quality and consistency.
• Establishes clear, measurable goals for projects and operational initiatives, and tracks progress towards those goals; translates these into actionable work plans for direct reports.
• Supervises, mentors, and evaluates staff; supports professional development and training.
• Identifies and implements best practices in operational and project management across the Benefits and Leave team.
• Continuously assesses workflows and systems to improve efficiency, stakeholder communication, and employee support services.
• Anticipates and resolves complex challenges to ensure the success of benefits and leave initiatives.
• Aligns team resources and priorities with broader DCPS initiatives and strategic goals.

Operations & Compliance

• Manages escalations across all benefits and leave workstreams, including Supplemental Retirement, Unemployment, and Death Claims.
• Ensure strong fiscal stewardship in the administration of employee benefits and leave programs by understanding implications to budget, analyzing cost drivers, identifying opportunities for savings, and implementing strategies that balance financial sustainability with employee satisfaction and compliance.
• Oversees vendor relationships for Benefits and Supplemental Retirement, including event coordination and performance oversight.
• Performs Tier 2 processing for Supplemental Retirement, including Retirement Manager system updates and loan overrides.
• Serves as a witness in DCPS unemployment hearings and acts as the point of contact for Department of Employment Services audits.
• Troubleshoots and resolves complex PeopleSoft issues related to benefits and leave.
• Processes Extended Leave, FMLA, and Paid Family Leave (PFML) requests.
• Administers benefits and leave accrual settlements, reinstatements, and year-end leave restoration.
• Coordinates benefits refunds with vendors and the Office of Pay and Retirement Services (OPRS), including 403(b) plans.

Stakeholder Engagement & Communication

• Builds strong relationships with internal and external stakeholders to support collaboration and project success.
• Communicates regularly with agency partners through meetings, email, and inter-agency forums.
• Ensures benefits and leave information is accessible and clearly communicated to all eligible DCPS employees.

Data & Policy Analysis

• Oversees the analysis and presentation of key benefits and leave data, including benefits enrollment trends and leave utilization.
• Shares progress updates with stakeholders and incorporates feedback into ongoing improvements.
• Monitors developments in benefits and leave policy and research; advises DCPS leadership on relevant legislation, policies, and directives.

Qualifications

• Bachelor’s degree, ideally in Human Resources, Business Administration, Public Administration, or a related field (Master’s preferred).
• 7–10 years of progressive experience in benefits and leave administration, including supervisory or managerial roles.
• Strong knowledge of federal and local employment laws (e.g., FMLA, PFML, ADA, unemployment).
• Experience with HRIS systems, preferably PeopleSoft.
• Demonstrated ability to lead strategic initiatives and manage complex operations.
• Excellent communication, analytical, and interpersonal skills.
• Ability to manage confidential information with discretion.
• Preferred Skills:
• HR or Benefits certification (e.g., CEBS, SHRM-SCP, SPHR).
• Experience in a public sector or unionized environment.
• Familiarity with retirement plan administration and audit processes.
• Previous exposure to or experience in the education sector a plus.

DCPS Values

• STUDENTS FIRST : We recognize students as whole children and put their needs first in everything we do.
• COURAGE : We have the audacity to learn from our successes and failures, to try new things, and to lead the nation as a proof point of PK-12 success.
• EQUITY : We work proactively to eliminate opportunity gaps by interrupting institutional bias and investing in effective strategies to ensure every student succeeds.
• EXCELLENCE : We work with integrity and hold ourselves accountable for exemplary outcomes, service, and interactions.
• TEAMWORK : We recognize that our greatest asset is our collective vision and ability to work collaboratively and authentically.
• JOY : We enjoy our collective work and will enthusiastically celebrate our success and each other.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Human Resources, Management, and Project Management

• Industries

  Human Resources Services and Insurance and Employee Benefit Funds

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Inferred from the description for this job

Medical insurance

Vision insurance

Paid maternity leave

Paid paternity leave

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