Senior Director Benefits & Employment Services

Milton Hershey School; Hershey (PA); On-site; USD 150,000 - 185,000; Full time

Job summary

Milton Hershey School seeks a Senior Director of Benefits & Employment Services to provide strategic leadership for employee and retiree benefits, employment services, and HR shared services across MHS and affiliated organizations. This role reports to the VP of HR and drives a high-quality employee experience through best-in-class programs and compliant operations.

The ideal candidate will lead a four-person team, oversee HIPAA privacy, and partner with Legal, Finance, and HR leaders to

Qualifications

• 10+ years of progressively responsible HR experience with leadership of benefits and HR operations.
• Experience managing complex health, welfare, and retirement programs.
• Strong knowledge of benefits compliance, financial planning, vendor management, and risk management.

Responsibilities

• Lead health, welfare, retirement, disability, and wellness programs for employees and retirees.
• Drive benefits strategy, plan design, financial planning, cost forecasting, and utilization analysis.
• Manage broker and vendor relationships, contract negotiations, and performance.
• Lead employment services and HR administrative functions with compliant service delivery.
• Oversee HR shared services integrating payroll, benefits, and service delivery.
• Serve as HIPAA Privacy Officer and oversee privacy practices.

Skills

Leadership

Strategic thinking

Communication

Analytical skills

Education

CEBS/SHRM-SCP

Job description

Job Description - Senior Director Benefits & Employment Services (26000192)

Senior Director Benefits & Employment Services - ( 26000192 )

Description

Milton Hershey School (MHS) is one of the world’s best pre‑K through 12th‑grade private schools, where approximately 2,200 students from disadvantaged backgrounds are provided with a cost‑free home and a top‑notch education. Thanks to the generosity of Milton and Catherine Hershey in 1909, the school is fully endowed today, with the resources to ensure students can thrive. The school has prepared over 12,000 graduates to lead fulfilling and productive lives and is expanding to serve more students for future generations.

MHS is seeking an accomplished Senior Director, Benefits & Employment Services to provide strategic leadership for employee and retiree benefits, employment services, and HR shared services supporting MHS and affiliated organizations. This leader reports to the Vice‑President of Human Resources and is responsible for ensuring competitive and financially sustainable benefits, strengthening HR operations and compliance, and delivering an exceptional employee experience.

Key Responsibilities

Benefits Strategy & Administration

• Lead health, welfare, retirement, disability, and wellness programs for employees and retirees.
• Drive benefits strategy, plan design, financial planning, cost forecasting, and utilization analysis.
• Manage broker and vendor relationships, contract negotiations, and performance.
• Evaluate benefits programs and recommend enhancements that strengthen competitiveness, employee experience, and financial sustainability.
• Ensure compliance with regulations and represent MHS in benefits‑related union negotiations and grievances.

Employment Services & HR Operations

• Lead employment services and HR administrative functions, ensuring accurate, timely, and compliant service delivery.
• Partner across HR to create an effective candidate‑to‑employee experience.
• Establish service standards, performance measures, and consistent processes.
• Streamline workflows and drive continuous improvement across HR operations.

HR Shared Services

• Oversee HR shared services supporting Catherine Hershey Schools (CHS), ensuring close integration of HR, payroll processes, and benefits administration.
• Partner with MHS and CHS leaders to ensure accurate and efficient service delivery.
• Enhance shared services processes, accountability, and the employees’ experience.

Compliance & Risk Management

• Serve as HIPAA Privacy Officer and provide oversight of applicable privacy practices.
• Co‑chair the Policy Committee and represent MHS HR on the CHS Policy Committee.
• Ensure compliance with relevant requirements, policies, audits, and internal controls.
• Partner with Legal, Finance, and HR leaders on compliance and risk matters.

Leadership & Organizational Effectiveness

• Lead, coach, and develop a benefits and employment services team of four.
• Foster accountability, collaboration, service excellence, and continuous improvement.
• Ensure team consistently models the school’s core values – commitment to mission, mutual respect, integrity and positive spirit.
• Leverage data and trends to improve services and inform strategic recommendations.
• Lead change initiatives to enhance HR operations and support evolving workforce needs.

Qualifications

• 10+ years of progressively responsible HR experience, including leadership of benefits and HR operations.
• Demonstrated expertise in complex health, welfare, and retirement programs.
• Depth & breadth of knowledge of benefits compliance, financial planning, vendor management, and risk management.
• Experience leading employment services, HR operations, or shared services.
• Proven ability to lead teams, improve processes, manage change, and influence across functions.
• CEBS, SHRM‑SCP, or related certification preferred.
• Excellent judgment, communication, analytical, and relationship‑building skills.
• High degree of integrity and commitment to serving as a positive role model for students.
• Eager to actively engage with students.
• Strategic Thinking: Anticipates future needs and aligns operational priorities with long‑term institutional goals.
• Driving for Results: Delivers measurable outcomes while effectively managing complexity and accountability.
• Courageous Communication: Builds trust through transparent, thoughtful, and decisive leadership.
• Coaching & Developing Others: Creates opportunities for growth, mentorship, and leadership development.

Why MHS?

This is an opportunity to shape benefits and HR services that directly support the people who make the MHS mission happen. The Senior Director will influence enterprise‑level strategy, strengthen the employee experience, and lead essential HR services.

Schedule

Full‑time

Job Type

Standard

Job Posting

Oct 29, 2026

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Milton Hershey School does not discriminate in admissions or other programs and services on the basis of race, color, national or ethnic origin, ancestry, sex, religious creed or disability. Read on equal opportunity and diversity, equal employment opportunity, and more. important MHS policies

Milton Hershey School does not discriminate in admissions or other programs and services on the basis of race, color, national or ethnic origin, ancestry, sex, religious creed or disability. . Equal Opportunity Policy