Regional Director – Multi-Site Operations (School-Based Childcare)
Healthy Kids Programs, Peekskill, NY, United States
Description
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.
Location & Structure
Location: Westchester County, NY (multiple program sites)
Salary: $60,000 – $65,000 annually (This role offers strong growth potential as the organization continues to expand.)
Reports To: Executive Director
Direct Reports: Site Directors and program staff
Featured Benefit: Employer‑Paid Childcare Healthy Kids Programs provides childcare for school‑age children (ages 5–12) enrolled in our program on the days and during the hours you work. Employer contributions cover the cost of care so you can focus on your job while your child participates in a safe, structured, and engaging program, all without needing to arrange outside care.
Why Join Healthy Kids Programs?
Lead operations across 10+ active childcare sites
Be part of a fast‑growing, mission‑driven organization (Inc. 5000 recognized)
Work closely with a supportive leadership team
Make a direct impact on children, families, and school communities
Access strong benefits, including employer‑paid childcare and professional development
What You’ll Be Responsible For
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
What This Role Looks Like Day‑to‑Day
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
What Success Looks Like
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
What It Takes To Succeed
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 preferred.
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
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
About 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.
This is a high‑impact leadership opportunity for a motivated professional ready to shape regional programs, support teams, and help expand Healthy Kids Programs’ mission across New York.
Learn more about working with us: https://www.healthykidsprograms.com/workwithus
Healthy Kids Programs is an equal opportunity employer. We are committed to fostering diversity, equity, and inclusion and prohibit discrimination based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic. Hiring decisions are based solely on qualifications, merit, and business needs.
#J-18808-Ljbffr
Location & Structure
Location: Westchester County, NY (multiple program sites)
Salary: $60,000 – $65,000 annually (This role offers strong growth potential as the organization continues to expand.)
Reports To: Executive Director
Direct Reports: Site Directors and program staff
Featured Benefit: Employer‑Paid Childcare Healthy Kids Programs provides childcare for school‑age children (ages 5–12) enrolled in our program on the days and during the hours you work. Employer contributions cover the cost of care so you can focus on your job while your child participates in a safe, structured, and engaging program, all without needing to arrange outside care.
Why Join Healthy Kids Programs?
Lead operations across 10+ active childcare sites
Be part of a fast‑growing, mission‑driven organization (Inc. 5000 recognized)
Work closely with a supportive leadership team
Make a direct impact on children, families, and school communities
Access strong benefits, including employer‑paid childcare and professional development
What You’ll Be Responsible For
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
What This Role Looks Like Day‑to‑Day
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
What Success Looks Like
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
What It Takes To Succeed
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 preferred.
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
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
About 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.
This is a high‑impact leadership opportunity for a motivated professional ready to shape regional programs, support teams, and help expand Healthy Kids Programs’ mission across New York.
Learn more about working with us: https://www.healthykidsprograms.com/workwithus
Healthy Kids Programs is an equal opportunity employer. We are committed to fostering diversity, equity, and inclusion and prohibit discrimination based on race, color, sex, religion, sexual orientation, national origin, disability, genetic information, pregnancy, or any other protected characteristic. Hiring decisions are based solely on qualifications, merit, and business needs.
#J-18808-Ljbffr