Regional Director – Multi-Site Operations (School-Based Childcare)

Healthy Kids ProgramsPeekskill, NY
$60,000 - $65,000Onsite

About The Position

We are seeking a Regional Director to lead operations across 10+ school-based childcare programs in Westchester County. This is a multi-site leadership role responsible for staffing, compliance, program performance, and regional growth. This is not a single-site position. You will oversee multiple locations, lead site directors, and ensure programs are running safely, smoothly, and successfully across your region. This is a highly hands-on, field-based role for someone who thrives in fast-paced environments, enjoys solving problems in real time, and can lead teams across multiple locations.

Requirements

  • Minimum of 5 years of leadership or supervisory experience in childcare, youth development, or education settings.
  • Experience overseeing multiple sites, programs, or teams
  • Background in: school-age childcare youth programs or multi-site service operations
  • Experience managing staffing, scheduling, and program performance
  • Knowledge of NY OCFS regulations
  • Experience with systems such as Paylocity and Playground
  • Strong communication, leadership, and organizational skills
  • Ability to travel regularly between sites
  • Valid driver’s license

Nice To Haves

  • Associate’s degree or higher in Early Childhood Education, Education, Child Development, or a related field preferred.

Responsibilities

  • Own the performance of 10+ licensed before/after school and summer camp programs
  • Recruit, train, and support Site Directors and staff
  • Ensure programs are fully staffed, in ratio, and compliant with OCFS regulations
  • Manage staffing coverage, payroll, and regional operations
  • Conduct regular site visits, coaching, and performance management
  • Build strong relationships with school partners, families, and communities
  • Support enrollment growth through outreach and engagement
  • Partner on new site launches and regional expansion

Benefits

  • Employer-paid childcare for children enrolled in our program, available during the days and hours you are scheduled to work
  • Medical, dental, and vision coverage
  • AFLAC Supplemental Plans
  • 401(k) retirement plan for eligible employees
  • Paid Holidays, PTO, and sick time
  • On-Demand Pay
  • Career development and growth opportunities

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What This Job Offers

Job Type

Full-time

Career Level

Director

Education Level

Associate degree

Number of Employees

1-10 employees

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