Transitional Living Assistant - Flex - Relocation to Hershey, PA Required

Company: Milton Hershey School
Location: Montgomery Village
Posted on: November 21, 2025

Job Description:

Description: Milton Hershey School (MHS) is a top-notch home and school where 2,000 pre-K through 12th grade students from disadvantaged backgrounds are provided an extra-ordinary cost-free career focused education. This is made possible by the generosity of Milton and Catherine Hershey, who established the school in 1909 and ensured it was fully endowed. Thanks to that foresight, the school has almost 12,000 graduates and is expanding to serve more students. MHS is hiring Flex Transitional Living Assistants (FTLA) to live with and supervise high school seniors in campus residence buildings in Hershey, PA. FTLA’s mentor MHS seniors to ensure they develop the life skills necessary for success post-graduation – whether they are entering post-secondary education, the military, or the world of work. FTLA's prepare students for the challenges they’ll face by role-modeling life skills and teaching self-responsibility, goal setting, planning & prioritization, time management, personal finance, and interpersonal skills - including appropriate dating behavior and managing peer pressure. Other responsibilities include creating and supervising evening & weekend recreational activities, taking students to Sunday chapel services, and collaborating with fellow staff members to continually evaluate and enhance the program. Additionally, FTLA’s provide coverage in MHS’s students homes as needed. This is a year-round position, working a schedule of 9 consecutive days, followed by 3 days off. Compensation includes a minimum annual salary of $48,799 plus a benefits package. Housing & utilities are provided. Up to $2,800 in relocation assistance is available. Qualifications: Bachelor's Degree required. Valid driver's license in good standing and an ability to become certified to drive a 9-passenger van. Experience working in youth residential settings a plus. Experience mentoring, teaching &/or advising diverse youth from under-served settings desired. Demonstrated success in developing & delivering life skills training is a plus. Exceptional interpersonal & leadership skills required including the ability to effectively manage conflict and inspire others. High degree of organizational skills & flexibility required. Computer skills including Microsoft & Google applications, Internet & social media. Because this is a live in position, the following parameters apply, only married spouses may reside in the apartment and overnight guests must be pre-approved. No pets, no smoking, and no weapons. No alcohol while on duty. Candidates should demonstrate a high degree of integrity, as all MHS staff are role models for students.

Keywords: Milton Hershey School, Montgomery Village , Transitional Living Assistant - Flex - Relocation to Hershey, PA Required, Education / Teaching , Montgomery Village, Maryland