Assistant Chess Instructor: Flexible Hours & Travel Pay

Chess Wizards, Inc.; Downers Grove (IL); On-site; USD 2,100 - 10,000; Full time

Benefits offered by this job

Full training

Curriculum provided

Free chess classes

Advancement opportunities

Work flexibility

Great company culture

Job summary

Chess Wizards, Inc. in Downers Grove, IL is seeking enthusiastic, reliable instructors to join our after-school enrichment program and share the magic of chess with elementary students. This is the perfect side-hustle for someone who can make learning fun and create a positive classroom environment.

As an Assistant Instructor you’ll help set up classes, provide student support, and travel to local schools. The position offers $40 per class, with weekday afternoons, mileage reimbursement, and

Qualifications

• Genuine interest in working with groups of elementary students.
• Experience (teaching, tutoring, camp counseling, or similar) is a plus.
• Ability to follow direction, support the Chess Instructor's classroom management, and help create interactive, friendly sessions.
• Professional, positive, and kid-friendly demeanor.
• Genuine desire to be a positive role model and promote good sportsmanship.
• Strong grasp of chess fundamentals; explain piece movement, basic strategy, and simple tactics in an age-appropriate way.
• Reliable personal transportation and the ability to drive between locations.
• Availability on weekday afternoons, with class start times between 2:00 PM and 5:00 PM to teach 1–5 classes per week.
• Commitment to safety protocols and reliable, punctual attendance.
• Strong punctuality and time-management skills.

Responsibilities

• Assist the Chess Instructor in setting up and managing a fun, interactive chess class for 15-22 elementary students.
• Provide one-on-one or small-group support to students, helping them practice piece movements and understand basic concepts.
• Support the Chess Instructor in guiding activities, keeping students engaged, and reinforcing positive behavior.
• Follow the structured curriculum and promote good sportsmanship alongside the Chess Instructor.
• 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.

Job description

Chess Wizards, Inc. in Downers Grove, IL is seeking enthusiastic, reliable instructors to join our after-school enrichment program and share the magic of chess with elementary students. This is the perfect side-hustle for someone who can make learning fun and create a positive classroom environment.

As an Assistant Instructor you’ll help set up classes, provide student support, and travel to local schools. The position offers $40 per class, with weekday afternoons, mileage reimbursement, and