Chess Instructor | Fall

Chess Wizards • Milton, MA

22d • $50 - $70 • Onsite

About The Position

Chess Wizards is seeking enthusiastic, reliable instructors to teach chess in its after-school enrichment program for elementary students in Milton, Massachusetts. Instructors lead interactive classes of 10–15 students using a structured curriculum to teach chess fundamentals and encourage good sportsmanship, problem-solving, creativity, and critical thinking. The role involves independently managing a lively classroom, following school safety protocols, supervising students during arrival, dismissal, and class activities, and traveling to local school sites. Instructors receive training, curriculum and materials, ongoing support, and free chess classes. The position offers flexible weekday-afternoon scheduling, with one to five classes per week depending on local school availability. Typical class time is approximately 90 minutes, including setup, instruction, and post-class responsibilities. Candidates must currently live in the Milton area or be willing to relocate at their own expense; relocation assistance is not provided.

Requirements

• Experience working with groups of children, such as through teaching, tutoring, coaching, or camp counseling.
• Comfort leading a class independently and creating interactive, friendly, and fun sessions.
• Professional, positive, kid-friendly demeanor.
• Genuine desire to be a positive role model and promote good sportsmanship.
• Strong grasp of chess fundamentals, including the ability to 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 ability to drive between locations.
• Availability on weekday afternoons, with class start times between 2:00 PM and 5:00 PM, for one to five classes per week depending on school availability.
• Commitment to implementing school safety protocols; reliability and strict adherence to safety and school policies are required because instructors supervise children independently.
• Strong punctuality and time-management skills.
• Resume detailing relevant experience working with children and any teaching, tutoring, or classroom experience.
• Completion of the required application questionnaire about interest in the role, experience working with children, and qualifications to teach chess.
• Currently residing in the Milton, Massachusetts area or willingness to relocate at personal expense.

Responsibilities

• Lead fun, interactive chess classes for groups of 10–15 elementary students.
• Use the structured curriculum to teach chess fundamentals and promote good sportsmanship.
• Manage the classroom confidently and positively, keeping students engaged and redirecting behavior as needed.
• Encourage problem-solving, creativity, and critical thinking, including connecting chess problem-solving to real-life problem-solving.
• Follow school safety protocols and supervise students during arrival, dismissal, and in-class activities.
• Travel to assigned local school sites for each session.
• Arrive on time, prepared, and ready to engage students.

Benefits

• Competitive pay of $50–$70 per class.
• Flexible hours, with one to five classes per week.
• Mileage reimbursement for trips exceeding 15 miles one way (30 miles roundtrip).
• Full training and ongoing support.
• Full curriculum and materials provided.
• Free chess classes.
• Opportunities for advancement.
• Work flexibility.
• Great company culture.

What This Job Offers

• Job Type: Full-time
• Education Level: No Education Listed