Enrichment and Supervision Leader, Middle School

Posted Yesterday
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95124, San Jose, CA, USA
In-Office
18-26 Hourly
Entry level
Edtech • Kids + Family • Professional Services
The Role
Lead and supervise middle school students during study hall, lunch, breaks, and after-school activities. Plan and run engaging programs, monitor behavior, enforce safety, conduct one-on-one check-ins, and participate in required training to support students' social and emotional development.
Summary Generated by Built In

The Harker School is currently searching for an Enrichment Specialist to join our Middle School Enrichment and Supervision Team for the 2026-2027 school year.

Are you ready to embark on a journey where every afternoon is an adventure?  We’re on the lookout for a creative individual to light up our program with energy, fun & enthusiasm as a Recreation Leader. You'll be more than a Rec Leader; you’ll be a mentor, a motivator, & a maker of memories. If you’re passionate about guiding middle school students to success & turning everyday activities into extraordinary experiences, this is the place for you.

We can’t wait to meet you! Apply today &  be a part of something special. 


  • Training Kickoff: Mark your calendar! Our adventure begins on Aug 18, 2026, with an exciting training session to gear you up for the year ahead.
  • Work Timeline: You’ll be with us from the first day of school Aug 24, 2026 through the final fun-filled day on June 3, 2027.
  • Work Hours: Your typical schedule will be from 12:00 PM to 5:30 PM (or 12:30 PM to 6:00 PM), but the exact hours will be tailored to meet the needs of our school & program, crafted in collaboration with our Directors.
Qualifications

Minimum Qualification Requirements

  • Age Requirements:  You must be 18 years old 
  • First Aid & CPR Certification:  Safety first!  You should have up-to-date certification in both first aid & CPR.  Don’t have it yet? No worries- we’ll provide them for you.
  • Experience with Children:  Prior experience working with kids recommended.
What’s in It for You?
  • Awesome Pay: Earn $23.00 - $25.00 per hour as you inspire & lead our future stars.
  • Creative Freedom: Plan activities that bring smiles & excitement for our students.
  • Team Collaboration:  Work alongside a passionate team dedicated to nurturing & inspiring young middle school students in a fun & supportive environment.

Essential Duties  Responsibilities: Your Role as a Rec Leader

  • Run Study Hall Classes: Lead focused/quiet study sessions when needed.THis may include touching base with students, communicate with teachers,&  one-on-one check-ins
  • Supervise Breaks, Lunches, & After-SChool:  Be friendly & vigilant presence ensuring students are safe & supported during free time.
  • Lunchtime & After-School Fun: Plan & run engaging activities that bring joy & guild community.
  • Student Development:  Oversee activities that contribute to the holistic development of each student, fostering their growth & well being.
  • Behavior Observation:  Monitor student behavior, assess situations, enforce safety regulations, & apply positive behavior management techniques.
  • Training: Participate in required training, deepening your understanding of adolescent emotional & social needs.

Knowledge, Skill & Ability Requirements:  

  • People Skills:  Your excellent interpersonal skills will help build strong, professional relationships with students, fellow staff, & coworkers.
  • Self-Motivation:  You’re driven & proactive, ready to take initiative without needing constant supervision.
  • Adaptability: You can roll with punches & juggle multiple tasks & scenarios.
  • Physical Stamina:  Be prepared to stand for 3 hours or more & walk the school grounds.
  • Climate Readiness:  Whether it’s sunny, rainy, chilly you can handle extremes.


Our Mission:

Our mission is to educate students for success at college and beyond, and to foster kindness, respect and integrity within a safe and nurturing environment. We achieve academic excellence through the development of intellectual curiosity, personal accountability and love of learning. Our comprehensive program and exceptional faculty and staff help students discover, develop and enjoy their unique talents. We honor individuality, embrace diversity, and promote leadership and service, preparing students to take their place as global citizens.


Skills Required

  • Must be 18 years old
  • Valid First Aid and CPR certification (or ability to obtain through employer-provided training)
  • Prior experience working with children
  • Available for training kickoff on Aug 18, 2026 and employment from Aug 24, 2026 to June 3, 2027
  • Availability to work typical afternoon schedule (approx. 12:00 PM–5:30 PM or 12:30 PM–6:00 PM) as assigned
  • Ability to stand for 3+ hours, walk school grounds, and perform physically active duties
  • Willingness to participate in required training on adolescent social and emotional needs
  • Strong interpersonal skills, adaptability, self-motivation, and positive behavior management techniques
Am I A Good Fit?
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The Company
0 Employees
Year Founded: 1893

What We Do

The Harker School is a coeducational, independent, college-preparatory day school serving students in TK-12th grade on three campuses in San Jose, California. Founded in 1893, its goal is to develop lifelong learners and well-rounded global citizens.

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