Chess Instructor | Fall

Area:
Boston, MA

Please note:

This vacancy is designated for the Fall season. Our recruitment team is currently interviewing 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!

• Competitive Pay: $50 – $70 per class (typical class length is approximately 1 hour 30 minutes, including setup and post‑class responsibilities)
• Flexible
  
  Hours:
  
  Teach a minimum of 1 class and a maximum of 5 classes per week, depending on availability at local schools. Classes are scheduled on weekday afternoons, typically between 2:00 PM and 5:00 PM.
• Travel Compensation:
  Mileage reimbursement for trips over 15 miles one way (30 miles roundtrip). Work locations are assigned by the manager based on available schools and classes in your area.

• Lead fun, interactive chess classes for 10–15 energetic elementary students.
• Use a 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.

• 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.
• Professional, positive, and kid‑friendly demeanor.
• Genuine desire to be a positive role model and promote good sportsmanship.
• Strong grasp of chess fundamentals; able to clearly and confidently explain piece movement, basic strategy, and simple tactics in an age‑appropriate way.
• Ability to connect game‑based problem‑solving to real‑life problem‑solving.
• Reliable personal transportation and ability to drive between locations.
• Availability on weekday afternoons (2:00 PM – 5:00 PM) to teach 1–5 classes per week, depending on school availability.
• Commitment to implementing school safety protocols to protect students’ well‑being. A strong record of reliability and adherence to safety and school policies is required.
• Strong punctuality and time‑management skills.

• Resume detailing relevant experience with children in educational, recreational, or mentoring settings, including teaching, tutoring, or classroom experience.
• Questionnaire related to interest in the role, experience working with children, and qualifications to teach chess.

• Full training and ongoing support.
• Full curriculum and materials.
• Opportunities for advancement.
• Work flexibility.
• Great company culture.

Location Requirement:
This position is based in Boston, MA. Candidates must be currently residing in the area or be willing to relocate at their own expense. Relocation assistance is not provided. Opportunities for classes in surrounding cities and suburbs may also be available.

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.