Chess Instructor | Fall

Chess Wizards • Milton, MA

20d • Onsite

About The Position

Chess Wizards is seeking enthusiastic, reliable instructors to teach chess in an after-school enrichment program for elementary students in Milton, Massachusetts. Instructors lead interactive classes for groups of 10–15 students using a structured curriculum, creating a positive classroom environment while teaching chess fundamentals, problem-solving, creativity, critical thinking, and good sportsmanship. The role involves supervising students and following school safety protocols, including during arrival, dismissal, and classroom activities, as well as traveling to assigned local school sites.

Classes take place on weekday afternoons, with start times typically between 2:00 PM and 5:00 PM. Instructors teach a minimum of one and a maximum of five classes per week, depending on local school availability. A typical class commitment is approximately 90 minutes, including setup, instruction, and post-class responsibilities. Pay is $50–$70 per class. Mileage reimbursement is provided for trips exceeding 15 miles one way from the instructor’s home or work location.

Chess Wizards provides full training, ongoing support, curriculum and materials, free chess classes, opportunities for advancement, work flexibility, and a positive company culture. The position is based in Milton, MA; relocation assistance is not provided. Applicants must currently live in the area or be willing to relocate at their own expense. Applicants must submit a resume and complete a required questionnaire.

Requirements

• Experience working with groups of children through teaching, tutoring, coaching, camp counseling, or similar work.
• Ability to lead a class independently and create interactive, friendly, and fun sessions.
• Upbeat, engaging, professional, positive, and 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 and strictly following safety and school policies while supervising children independently.
• Strong punctuality and time-management skills.
• Submit a resume detailing relevant experience with children, including educational, recreational, mentoring, teaching, tutoring, or classroom experience.
• Complete the required application questionnaire about interest in the role, experience working with children, and qualifications to teach chess.
• Currently reside in the Milton, MA area or be willing to relocate at personal expense; relocation assistance is not provided.

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.
• Guide activities, keep students engaged, and redirect behavior when needed.
• Manage a lively classroom with confidence and positivity.
• Encourage problem-solving, creativity, and critical thinking.
• Follow school safety protocols and supervise students during arrival, dismissal, and in-class activities.
• Travel to various assigned local school sites for each session.
• Arrive on time, prepared, and ready to engage students.

Benefits

• Competitive pay of $50–$70 per class.
• Mileage reimbursement for trips over 15 miles one way from home or work location.
• 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: Part-time
• Career Level: Entry Level
• Education Level: No Education Listed