Chess Instructor | Fall

Area: Milton, MA

Please Note: This vacancy is designated for the Fall season. Our recruitment team is currently conducting interviews for sessions scheduled to start in late summer/early fall.

Do you love chess? Do you enjoy working with kids?

Chess Wizards is seeking enthusiastic, reliable instructors to join our after-school enrichment program! If you can make learning fun, create a positive classroom environment, and share the magic of chess with elementary students, this is the perfect side-hustle. Apply today and get paid to teach chess!

Why Join Us?

• Competitive Pay: $50 - $70 per class (Typical class time is approximately one hour and thirty minutes which includes pre-class setup, instructional time, and post-class responsibilities)
• Flexible Hours: Teach a minimum of 1 class up to a maximum of 5 classes per week. The specific number is based on the availability of classes at local schools in your area. Classes are scheduled on weekday afternoons, with start times typically falling between 2:00 PM and 5:00 PM at various local schools
• Travel Compensation: Mileage reimbursement provided for trips over 15 miles one way (30 miles roundtrip), from your home or work location. Work locations are assigned by the manager based on available schools and classes in your area.

What You’ll Do

• Lead fun, interactive chess classes for 10–15 energetic elementary students. Instructors should be comfortable guiding activities, keeping students engaged, and redirecting behavior when needed
• Use our structured curriculum to teach chess fundamentals and promote good sportsmanship
• Manage a lively classroom with confidence and positivity
• Encourage problem-solving, creativity, and critical thinking
• Follow school safety protocols, including supervision during arrival, dismissal, and in-class activities.
• Travel to various local school sites for each session
• Arrive on time, prepared, and ready to engage students

What We’re Looking For

Required

• Experience working with groups of children (teaching, tutoring, coaching, camp counseling, or similar)
• Comfort leading a class independently and creating interactive, friendly, and fun sessions. We seek upbeat, engaging instructors.
• Professional, positive, and kid-friendly demeanor
• Genuine desire to be a positive role model and promote good sportsmanship
• Strong grasp of chess fundamentals. You should be able to clearly and confidently explain piece movement, basic strategy, and simple tactics in an age-appropriate way.
• Ability to connect chess problem-solving to real-life problem-solving
• Reliable personal transportation and the ability to drive between locations.
• Availability on weekday afternoons, with class start times falling within the 2:00 PM to 5:00 PM window, to teach 1–5 classes per week. The specific number of classes depends on availability at local partner schools.
• Commitment to implementing school safety protocols to protect students’ well-being. Because you will supervise children independently, a strong record of reliability and strict adherence to safety and school policies is required.
• Strong punctuality and time-management skills

Application Requirements

• Resume : Include a resume detailing your relevant experience, including working with children in educational, recreational, or mentoring settings, as well as any teaching, tutoring, or classroom experience.
• Questionnaire : As part of your application, you will be asked to complete a required questionnaire related to your interest in the role, your experience working with children, and your qualifications to teach chess, among other topics

Chess Wizards Instructors receive full training and ongoing support. Full curriculum and materials. Free chess classes. Opportunities for advancement. Work flexibility. Great company culture!

Location Requirement : This position is based in Milton, MA . Please note that relocation assistance is not provided. Candidates must be currently residing in the area or be willing to relocate at their own expense.

Chess Wizards is an Equal Opportunity Employer . All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.