Director of Student Success

WISDOM AND WONDER ENDEAVORS INC • Lake Mary, FL

15h • $45,000 - $70,000 • Hybrid

About The Position

The Director of Student Success leads the full student and family experience from initial inquiry through long-term enrollment while managing daily operations, growing the center’s reach, and coaching a team of educators. This is a visible leadership role that puts your educational background to work in a new way: building relationships with families, connecting with local schools, and running a center that makes a real difference in students’ lives. The ideal candidate brings the credibility of an educator and the drive of an entrepreneur. You take pride in student outcomes and enrollment growth in equal measure, and you understand that a thriving center is what makes the mission possible. We’ll train the rest!

Requirements

• Bachelor’s degree required
• At least three years of experience working with K-12 students in a teaching, tutoring, or academic coaching capacity
• Strong understanding of K-12 reading and math instruction
• Natural ability to connect with families, earn trust quickly, and guide people toward confident decisions
• Comfort reading and interpreting business metrics, enrollment reports, and basic financial statements
• Excellent interpersonal and communication skills; comfortable presenting to small groups, parents, and school staff
• Proficiency with Microsoft Office, Google Workspace, and standard business applications
• Comfort with instructional technology, tablet-based learning platforms, and social media
• Strong organizational skills with the ability to manage multiple priorities in a fast-paced environment
• Genuine passion for children’s academic success and family engagement
• Enthusiasm, confidence, and results driven
• Outgoing, people-oriented, and energized by community interaction
• High integrity, self-motivated, and accountable to outcomes
• Ability to occasionally lift up to 10 pounds

Nice To Haves

• Degree in Education, Early Childhood Education, English, mathematics, science or a closely related field strongly preferred
• Florida teaching certification (active or eligible) is a significant plus
• Some experience in a customer-facing or leadership role is a plus
• Familiarity with Florida B.E.S.T. standards preferred

Responsibilities

• Manage the day-to-day operation of the Center, ensuring a consistent, high-quality student experience aligned with Sylvan standards
• Oversee student safety, center appearance, and adherence to all Sylvan operating procedures
• Review and act on corporate communications; ensure timely flow of information to staff
• Step in as a qualified tutor when staffing needs arise, providing direct instruction in reading and/or mathematics using Sylvan’s research-based programs
• Support instructional quality by monitoring student progress, interpreting assessment data, and ensuring program fidelity
• Contribute academic expertise to individualized learning plan reviews and parent-facing progress conferences
• Respond promptly to all inbound inquiries (phone, walk-in, online) with a warm, family-first approach
• Guide families through the enrollment process, helping them understand how Sylvan’s programs can meet their child’s needs
• Present program options and financing solutions that fit each family’s situation
• Grow and sustain the center’s enrollment by building trust and delivering a great experience that keeps families coming back
• Build and maintain relationships with local school staff including guidance counselors, classroom teachers, and literacy/math specialists to generate referrals and stay connected to student needs in the community
• Conduct proactive school visits and represent Sylvan at school events, parent nights, and community functions
• Promote specific programs (SAT/ACT prep, subject tutoring, reading intervention) directly to school counselors and administrators as appropriate
• Collaborate with parent/teacher organizations and community groups to expand Sylvan’s visibility and referral network
• Recruit, hire, train, and coach center staff; conduct regular performance reviews
• Manage staff scheduling and ensure appropriate instructional coverage at all times
• Drive local marketing activities including social media, referral programs, and seasonal campaigns to generate new enrollments
• Monitor financial statements, track center performance metrics, and recommend interventions to address variances

Benefits

• Bonus based on performance
• Competitive salary
• Flexible schedule
• Training & development
• Benefits package discussed during the interview process

What This Job Offers

• Job Type: Full-time
• Career Level: Manager