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

Healthy Kids Programs · Mount Kisco, NY · Yesterday

On-siteEducation$65k–$70k/yrFull-time

We are seeking a Regional Director to lead operations across 10+ school-based childcare programs in Westchester County. This multi-site leadership role is responsible for staffing, compliance, program performance, and regional growth.

About the Role

Oversee multiple locations, lead site directors, and ensure programs are running safely, smoothly, and successfully across your region.
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.

Location: Grafflin Elementary School in Chappaqua, NY
Territory: Westchester County, NY (multiple program sites)
Reports To: Executive Director
Direct Reports: Site Directors and program staff

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.

Day-to-Day Activities

Visiting multiple sites each week and coaching leaders in real time.
Addressing staffing gaps and ensuring coverage across locations.
Solving operational challenges quickly and effectively.
Supporting site leaders through performance and team development.
Monitoring enrollment and adjusting strategies to meet goals.

Success Metrics

Programs consistently operating in ratio and in compliance.
Strong, stable leadership teams across sites.
High-quality program execution and staff engagement.
Enrollment targets met and sustained.
Strong relationships with school partners and families.

Requirements

Ability to manage multiple priorities and locations at once.
Confidence making decisions in fast-paced, real-time situations.
Strong leadership presence in the field.
Willingness to be hands-on and visible across sites.
Comfort navigating staffing and operational challenges.

Qualifications

Strongly Preferred:

Associate’s degree or higher in Early Childhood Education, Education, Child Development, or a related field.
Minimum of 5 years of leadership or supervisory experience in childcare, youth development, or education settings.
Experience working for a multi-site childcare or youth-serving organization, preferably within a for-profit or growth-oriented environment.
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.

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.

Pay

$65,000 – $70,000 annually (This role offers strong growth potential as the organization continues to expand.)

About Healthy Kids Programs

Healthy Kids Programs is a rapidly growing provider of Early Learning, Before & After School, and Summer Camp programs, serving over 100 locations across New York. We are a certified benefit corporation committed to high-quality, accessible childcare and meaningful career pathways for our team. Recognized on Inc. 5000’s Fastest-Growing Companies, we offer a collaborative, mission-driven workplace where leaders are empowered to grow, innovate, and make a real impact.