Regional Director– Multi-Site Childcare Programs

Location: Multiple program locations in Westchester County, NY

Salary: $60,000 – $65,000 annually

Reports To: Executive Director

Direct Reports: Program Site Directors and Site Staff

Featured Benefit: Employer-Paid Childcare

Healthy Kids Programs provides childcare for children enrolled in program during the days and hours you work. Employer contributions cover the cost of care so you can focus on your work while your child participates in a safe, structured, and engaging program.

Why Join Healthy Kids Programs?

• Lead and inspire multiple childcare programs in a hands-on, high-impact role
• Be part of a fast-growing, mission-driven organization recognized on Inc. 5000’s Fastest-Growing Companies
• Make a meaningful difference in children’s lives and the community
• Collaborate with a supportive leadership team and grow your professional career
• Enjoy exceptional benefits, including employer-paid childcare and professional development

About the Role

We are seeking an experienced Regional Director to oversee multiple school-based childcare programs across Westchester County. You will provide operational leadership, ensure program quality and compliance, support site leadership teams, and foster strong relationships with families, schools, and community partners. This is a hands-on role, requiring regular travel and active participation in site operations.

Key Responsibilities

• Oversee 10 licensed sites for Before & After School and Summer Camp programs
• Recruit, train, supervise, and support Site Directors and program staff
• Ensure compliance with New York OCFS regulations (ratios, safety, program standards)
• Conduct site visits, performance coaching, and staff development
• Manage staffing coverage, payroll, and regional budgets
• Build and maintain relationships with schools, families, and community partners
• Support enrollment growth through marketing, outreach, and engagement
• Collaborate on new site launches and regional expansion

Success in This Role

• Programs consistently operating in ratio and in compliance
• Strong, stable site leadership teams
• Regular site visits and meaningful coaching for staff
• Enrollment growth and high family satisfaction
• Strong partnerships with school districts

This role is ideal for a hands-on leader who enjoys working in the field, coaching teams, and ensuring operational excellence across multiple program locations.

Qualifications

• 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.
• At least 2 years of hands-on experience working with children under 13, ideally in licensed childcare programs.
• Strong knowledge of New York OCFS childcare regulations and licensing requirements.
• Experience with HRIS platforms (e.g., Paylocity) and registration/attendance systems (e.g., Playground).
• Proficiency in Microsoft 365 applications, including Outlook, Excel, Word, and Teams.
• Excellent leadership, communication, and organizational skills.
• Ability to travel regularly between program sites in the region.
• Valid driver’s license required.
• Must meet all OCFS background check and health requirements.

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

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.