Regional Director – Multi-Site Operations (School-Based Childcare)

DescriptionWe 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 & StructureLocation: 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 DirectorDirect Reports: Site Directors and program staffFeatured Benefit: Employer-Paid ChildcareHealthy 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 sitesBe part of a fast-growing, mission-driven organization (Inc. 5000 recognized)Work closely with a supportive leadership teamMake a direct impact on children, families, and school communitiesAccess strong benefits, including employer-paid childcare and professional developmentWhat You’ll Be Responsible ForOwn the performance of 10+ licensed before/after school and summer camp programsRecruit, train, and support Site Directors and staffEnsure programs are fully staffed, in ratio, and compliant with OCFS regulationsManage staffing coverage, payroll, and regional operationsConduct regular site visits, coaching, and performance managementBuild strong relationships with school partners, families, and communitiesSupport enrollment growth through outreach and engagementPartner on new site launches and regional expansionWhat This Role Looks Like Day-to-DayVisiting multiple sites each week and coaching leaders in real timeAddressing staffing gaps and ensuring coverage across locationsSolving operational challenges quickly and effectivelySupporting site leaders through performance and team developmentMonitoring enrollment and adjusting strategies to meet goalsWhat Success Looks LikePrograms consistently operating in ratio and in complianceStrong, stable leadership teams across sitesHigh-quality program execution and staff engagementEnrollment targets met and sustainedStrong relationships with school partners and families What It Takes To SucceedAbility to manage multiple priorities and locations at onceConfidence making decisions in fast-paced, real-time situationsStrong leadership presence in the fieldWillingness to be hands-on and visible across sitesComfort navigating staffing and operational challengesRequirementsQualifications (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 teamsBackground in:school-age childcareyouth programsor multi-site service operationsExperience managing staffing, scheduling, and program performanceKnowledge of NY OCFS regulationsExperience with systems such as Paylocity and PlaygroundStrong communication, leadership, and organizational skillsAbility to travel regularly between sitesValid driver’s licenseBenefitsEmployer-paid childcare for children enrolled in our program, available during the days and hours you are scheduled to workMedical, dental, and vision coverageAFLAC Supplemental Plans401(k) retirement plan for eligible employeesPaid Holidays, PTO, and sick timeOn-Demand PayCareer development and growth opportunitiesAbout Healthy Kids ProgramsHealthy 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/workwithusHealthy 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.