Senior Director Benefits & Employment Services

Mhskids; Hershey (PA); On-site; USD 150,000 - 230,000; Full time

Job summary

Milton Hershey School seeks a Senior Director of Benefits & Employment Services to provide strategic leadership over employee and retiree benefits, employment services, and HR shared services. This role reports to the Vice-President of Human Resources and focuses on competitive, financially sustainable programs and exceptional employee experience.

The leader will direct benefits strategy, HR operations, and shared services across MHS and CHS, ensuring compliance, risk management, and alignment

Qualifications

• 10+ years HR experience, including leadership of benefits and HR operations.
• Expertise in health, welfare, and retirement programs.
• Knowledge of benefits compliance, financial planning, vendor management, and risk management.
• Experience leading employment services or shared services.
• Proven ability to lead teams and influence across functions.
• Strong judgment, communication, analytical and relationship-building skills.
• Integrity and commitment to serving as a positive role model.

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.
• Evaluate benefits programs and recommend enhancements that strengthen competitiveness and financial sustainability.
• Ensure compliance with regulations and represent MHS in benefits-related union negotiations and grievances.
• 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.
• Oversee HR shared services supporting CHS, ensuring integration with payroll 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.

Skills

Leadership

Benefits design

HR operations

Vendor management

Strategic thinking

Education

CEBS / SHRM-SCP

Job description

Senior Director Benefits & Employment Services

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.

Milton Hershey School does not discriminate against applicants or employees, in hiring, promotion or any terms or conditions of employment, on the basis of race, color, national or ethnic origin, ancestry, sex, age, religion or religious creed, veteran status, disability or use of a guide or support animal because of the blindness, deafness or physical handicap of the user or because the user is a handler or trainer of support or guide animals, or any other status protected under applicable federal or Pennsylvania law.

Milton Hershey School will not tolerate any form of harassment or discrimination on the basis of race, color, national or ethnic origin, ancestry, sex, age, religion or religious creed, veteran status, disability, or any other status protected under applicable federal or Pennsylvania law (collectively "Protected Characteristics"), against any applicant for admission, enrolled student, or any other individual(s) who participate(s) in the programs, services, and activities of the School. Read important MHS policies on equal opportunity and diversity, equal employment opportunity, and more.