Youth Program Director Jobs in Ridgefield, CT (NOW HIRING)

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.

• Location: Grafflin Elementary School in Chappaqua, NY
• Territory: Westchester County, NY (multiple program sites)
• Salary: $65,000 – $70,000 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 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

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.