Regional Director Multi-Site Operation

Location & Structure

Location: Headquarters, 2 Summit Court, Fishkill, NY 12524
Territory: Dutchess County and Westchester County, NY (multiple program sites)
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

Requirements & Qualifications (Strongly Preferred)

• Associates 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 drivers license