Part Time Director of Enrichment Program

Director – Traverse Square Enrichment Programs

Position Type: Part-Time / Seasonal (Supervisory)

Compensation: $30 / hour (20 hours/week across 23 employment weeks; up to 5 additional hours for meetings)

This position is for an initial two-year contact.

Location: Traverse Square, Middletown, CT

Employer: Oddfellows Playhouse (in partnership with the Middletown Housing Authority & Wesleyan University’s Jewett Center)

About the Role

The Director of Traverse Square Enrichment Programs is an exciting leadership role created through a new partnership between the Middletown Housing Authority, Oddfellows Playhouse, and the Jewett Center for Community Partnerships at Wesleyan University.

Employable through Oddfellows Playhouse, the Director will oversee a daily Monday–Friday afterschool program providing high-quality educational, creative, and social enrichment to resident youth. The Director directly supervises two Oddfellows Program Coordinators, two Wesleyan Student Coordinators, and a team of nearly 50 Wesleyan student tutors and volunteers.

Program Schedule & Daily Operations

The program runs for 21–22 active academic weeks per year during the Wesleyan University school calendar, divided into two cycles:

• Fall Cycle: October – Mid-December (~11 weeks)
• Spring Cycle: February – Mid-May (~10 weeks)

Work Hours & Shift Breakdown

• Director Schedule: Monday–Friday, 3:00 PM – 7:00 PM (4 hours/day; 20 hours/week).
• Program Operating Hours: Monday–Friday, 4:00 PM – 6:00 PM.
• Staff On-Site Prep/Wrap-Up: Coordinators on-site 3:30 PM – 6:30 PM.

Daily Program Structure

• 4:00 PM: Student arrival, greeting, sign-in, and healthy snack.
• Academic Time: Homework assistance and one-on-one/small-group tutoring.
• Enrichment Silos: Rotational daily thematic activities (arts, creative learning, life skills).
• 6:00 PM: Dismissal and facility closing.

Key Responsibilities

Management & Supervision

• Provide overall leadership, administrative oversight, and daily direction for the program.
• Directly supervise two Oddfellows Program Coordinators, student coordinators, and volunteer staff.
• Ensure the facility is fully staffed, open on time, and safely operated during all posted hours.

Operations & Logistics

• Maintain accurate records for student attendance, staff hours, and volunteer service tracking.
• Procure, manage, and inventory program resources, snacks, art supplies, and technology (e.g., iPads).
• Serve as the main point of contact between Oddfellows Playhouse, Middletown Housing Authority, and the Jewett Center for Community Partnerships (JCCP).
• Collaborate with Jewett Center and Wesleyan staff to connect program families with on-campus and community events.

Safety & Compliance

• Ensure full adherence to Oddfellows Playhouse, Housing Authority, and Wesleyan University policies, alongside relevant local, state, and federal regulations.
• Enforce all health, safety, and operational guidelines.
• Complete required certifications and ensure all primary staff complete mandatory onboarding clearances.

Required Clearances & Certifications

Paid training time and course fees are fully covered by Oddfellows Playhouse.

• Mandatory Reporter Training
• Pediatric First Aid, CPR & AED Certification
• EpiPen Administration Certification
• Psychological / Trauma-Informed First Aid Training

Qualifications

• Proven experience working with youth and leading educational or enrichment programs.
• Demonstrated track record in staff and volunteer management.
• Strong communication, organizational, and interpersonal skills.
• Ability to build collaborative relationships across multiple organizational partners.
• Position subject to pre-employment screening and comprehensive background check.

How to Apply

To apply, please submit your cover letter resume and cover letter to wesley@oddfellows.org.

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