After-School Chess Instructor — Flexible Hours & Travel Pay

Chess Wizards, Inc.; Milton (MA); On-site; USD 69,000 - 96,000; Part time

Benefits offered by this job

Free chess classes

Full training and ongoing support

Opportunities for advancement

Work flexibility

Great company culture

Job summary

Chess Wizards, Inc. is seeking enthusiastic instructors to join our Milton, MA after-school enrichment program.

You will lead fun, interactive chess classes for elementary students, using a structured curriculum to teach fundamentals and good sportsmanship in a positive learning environment. Ideal candidates have experience working with children, a friendly, proactive attitude, and reliable transportation to travel between local schools.

Qualifications

• Experience working with groups of children in educational, recreational, or mentoring settings.
• Ability to lead a class independently and create engaging, kid-friendly sessions.
• Strong, positive, professional demeanor around students, staff, and schools.

Responsibilities

• Lead fun, interactive chess classes for 10–15 elementary students.
• Use structured curriculum to teach chess fundamentals and sportsmanship.
• Manage a lively classroom with confidence and positivity.
• Encourage problem-solving, creativity, and critical thinking.
• Follow school safety protocols during arrival, dismissal, and activities.
• Travel to local school sites for each session.
• Arrive on time, prepared, and ready to engage students.

Skills

Group instruction

Public speaking

Professional demeanor

Punctuality

Chess fundamentals

Problem solving

Reliable transportation

Weekday availability

Safety compliance

Job description

Chess Wizards, Inc. is seeking enthusiastic instructors to join our Milton, MA after-school enrichment program.

You will lead fun, interactive chess classes for elementary students, using a structured curriculum to teach fundamentals and good sportsmanship in a positive learning environment. Ideal candidates have experience working with children, a friendly, proactive attitude, and reliable transportation to travel between local schools.