Chess Instructor | Fall

Chess Wizards • Milton, MA

42d • Onsite

About The Position

Chess Wizards is seeking enthusiastic, reliable instructors to join their after-school enrichment program for the Fall season. The role involves making learning fun, creating a positive classroom environment, and sharing the magic of chess with elementary students. It is described as a perfect side-hustle for those who love chess and enjoy working with kids, offering competitive pay and flexible hours. Instructors will receive full training, ongoing support, curriculum, and materials, along with opportunities for advancement within a great company culture. The recruitment team is currently conducting interviews for sessions scheduled to start in late summer/early fall.

Requirements

• 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
• Upbeat, engaging demeanor
• 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 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
• Commitment to implementing school safety protocols to protect students’ well-being
• Strong record of reliability and strict adherence to safety and school policies
• Strong punctuality and time-management skills
• Resume detailing relevant experience, including working with children in educational, recreational, or mentoring settings, as well as any teaching, tutoring, or classroom experience
• Completion of a required questionnaire related to interest in the role, experience working with children, and qualifications to teach chess

Responsibilities

• Lead fun, interactive chess classes for 10–15 energetic elementary students
• Guide activities, keep students engaged, and redirect 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

Benefits

• Competitive Pay: $50 - $70 per class
• Flexible Hours: Teach a minimum of 1 class up to a maximum of 5 classes per week
• Travel Compensation: Mileage reimbursement provided for trips over 15 miles one way (30 miles roundtrip)
• Full training and ongoing support
• Full curriculum and materials
• Free chess classes
• Opportunities for advancement
• Work flexibility
• Great company culture!

What This Job Offers

• Job Type: Part-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 11-50 employees