Director of Student Success

WISDOM AND WONDER ENDEAVORS INC; Florida; On-site; USD 45,000 - 70,000; Full time

Benefits offered by this job

Bonus based on performance

Competitive salary

Flexible schedule

Training & development

Job summary

Wisdom and Wonder Endeavors Inc. dba Sylvan Learning Center in Lake Mary, FL, seeks a Director of Student Success to lead the center’s student and family experience from inquiry through enrollment, while overseeing daily operations and coaching educators.

You will expand the center’s reach and partner with local schools to deliver measurable student outcomes. The ideal candidate combines educational credibility with entrepreneurial drive, focusing on student results and enrollment growth;

Qualifications

• Bachelor’s degree required; degree in Education or related field preferred.
• Florida teaching certification is a significant plus.
• At least three years of experience with K-12 students in teaching, tutoring, or coaching.
• Customer-facing or leadership experience a plus; driven and coachable.

Responsibilities

• Lead day-to-day center operations ensuring a high-quality student experience.
• Oversee safety, center appearance, and adherence to Sylvan procedures.
• Monitor progress, interpret assessments, and ensure program fidelity.
• Build relationships with families, schools, and the community.
• Recruit, hire, and coach center staff; manage scheduling.
• Drive local marketing and enrollment growth; analyze center metrics.

Skills

Leadership

Strategic thinking

Student engagement

Communication

Coaching

Enrollment growth

Operations management

Education

Bachelor’s degree

Florida teaching certification

Tools

Microsoft Office

Google Workspace

Job description

Benefits:

Bonus based on performance

Competitive salary

Flexible schedule

Training & development

About the Role

Are you an experienced educator with a passion for student success and the drive to lead a growing business? Do you love seeing your effort make a difference in the lives of families? Do you want to lead one of the largest and fastest-growing Sylvan franchises in the entire system of 500+ locations worldwide? Do you desire a flexible schedule that enables you to balance your life and work? Come join us at Sylvan Learning of Lake Mary & Longwood!

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. You bring these traits, and we’ll train the rest!

Compensation & Schedule

• Total compensation range: $45,000–$70,000, with earnings based on a combination of base pay and performance incentives tied to enrollment and revenue growth • Schedule flexibility including occasional weekends • Benefits package discussed during the interview process

What You’ll Do

Operations & Quality • 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

Instruction & Academic Support • 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

Enrollment & Family Engagement • 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

School & Community Relationships • 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

Team Leadership & Marketing • 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

What We’re Looking For

Education & Background • Bachelor’s degree required; 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 • At least three years of experience working with K-12 students in a teaching, tutoring, or academic coaching capacity • Some experience in a customer-facing or leadership role is a plus, but if you have the right instincts and drive, we’ll help you develop the rest

Knowledge & Skills • Strong understanding of K-12 reading and math instruction; familiarity with Florida B.E.S.T. standards preferred • 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

Personal Attributes • 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

Why Sylvan Learning of Lake Mary? • Join one of the largest and fastest-growing Sylvan franchises in a system of 500+ locations with real infrastructure, strong brand recognition, and proven programs behind you • Serve students and families in the Lake Mary and Longwood communities, one of Central Florida’s fastest-growing areas • Be part of a growing organization with genuine opportunities for advancement as we scale • Earn between $45,000 and $70,000 based on your performance • Make a measurable difference in student outcomes using research-based instructional programs with decades of proven results

About Us:

Wisdom and Wonder Endeavors Inc. dba Sylvan Learning Center is an organization rooted in the belief that every student has the potential to thrive. Based in Lake Mary, FL, we are committed to delivering innovative educational experiences that inspire curiosity, build confidence, and unlock lifelong success. Our team is passionate, collaborative, and united by a shared mission to make a meaningful difference in the lives of the students we serve.