Lead Teacher & Program Manager - Orlando

About the role

We’re the only program in the world that teaches children as young as 3 to play chess - completely through stories, characters, and play. With thousands of kids learning every week across NYC, LA, and beyond, we’re expanding and looking for leaders who want to grow with us. Story Time Chess Orlando launched in 2025 and has grown rapidly - from zero to 40 schools in under a year. You’d be joining a growing team, teaching a curriculum that’s ready to deliver from day one, and helping to shape something special in Orlando.

Responsibilities

• Teach great classes
• Deliver fun, engaging Story Time Chess lessons in schools and community programs across the Orlando area.
• Bring strong storytelling and classroom management skills to every class.
• Serve as the “gold standard” model of our curriculum that other tutors learn from.
• Lead and support our tutor team
• Interview, onboard, and train new tutors.
• Observe, coach, and mentor tutors to ensure quality and consistency in every classroom.
• Be a positive, supportive leader who tutors enjoy working with and learning from.
• Care for day-to-day operations
• Manage tutor scheduling, lesson delivery, and reporting.
• Troubleshoot the everyday challenges of running classes across multiple school sites.
• Be the friendly, reliable point of contact for school partners, tutors and parents.

Requirements

• Experience with teaching or working with children ages 3–8.
• A natural storyteller with strong classroom presence.
• Experience with leading or mentoring a team.
• Organized and comfortable with managing day-to-day administrative tasks.
• High-energy, positive, and aligned with our mission: making learning joyful, memorable, and impactful.
• Reliable transportation and willingness to travel between school sites across the Orlando area as needed (including Winter Park, Winter Garden, Clermont, Lake Nona, and Sanford).
• Familiarity with chess fundamentals is a bonus, but not essential.

Qualifications

• Experience with teaching or working with children ages 3–8.
• A natural storyteller with strong classroom presence.
• Experience with leading or mentoring a team.
• Organized and comfortable with managing day-to-day administrative tasks.
• High-energy, positive, and aligned with our mission: making learning joyful, memorable, and impactful.
• Reliable transportation and willingness to travel between school sites across the Orlando area as needed (including Winter Park, Winter Garden, Clermont, Lake Nona, and Sanford).
• Familiarity with chess fundamentals is a bonus, but not essential.

Skills

• Experience with teaching or working with children ages 3–8.
• A natural storyteller with strong classroom presence.
• Experience with leading or mentoring a team.
• Organized and comfortable with managing day-to-day administrative tasks.
• High-energy, positive, and aligned with our mission: making learning joyful, memorable, and impactful.
• Reliable transportation and willingness to travel between school sites across the Orlando area as needed (including Winter Park, Winter Garden, Clermont, Lake Nona, and Sanford).
• Familiarity with chess fundamentals is a bonus, but not essential.

Benefits

• Full-time salary: $45,000 – $60,000, based on experience
• Fuel stipend: $100 per month to offset any transportation costs
• Paid time off
• Paid training
• Opportunity to lead and shape a growing educational team
• A role where fun and excellence go hand-in-hand

Pay

• Full-time salary: $45,000 – $60,000, based on experience

Schedule

• Flexible schedule

What We Offer

• Full-time salary: $45,000 – $60,000, based on experience
• Fuel stipend: $100 per month to offset any transportation costs
• Paid time off
• Paid training
• Opportunity to lead and shape a growing educational team
• A role where fun and excellence go hand-in-hand

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