Regional Director – Multi-Site Operations (School-Based Childcare)
About the Role
We are seeking a Regional Director to lead operations across 10+ school-based childcare programs in Dutchess and 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.
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
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
Pay & Schedule
Salary: $65,000 – $70,000 annually (This role offers strong growth potential as the organization continues to expand.)
Location: Dutchess County and Westchester County, NY (multiple program sites)
Reports To: Executive Director
Direct Reports: Site Directors and program staff