Chess Instructor | Fall

Chess Wizards, Inc; Weston (CT); On-site; USD 1,800 - 2,700; Full time

Benefits offered by this job

Competitive pay

Flexible hours

Travel reimbursement

Full training and ongoing support

Curriculum and materials provided

Free chess classes

Advancement opportunities

Job summary

Chess Wizards, Inc. in Weston, CT is seeking enthusiastic, reliable instructors to join our after-school enrichment program. If you can make learning fun, create a positive classroom environment, and share the magic of chess with elementary students, this is the perfect side-hustle.

You'll lead interactive chess classes for 10-15 children, follow our curriculum, maintain safety and classroom energy, and travel between local school sites with a flexible schedule of 1–5 classes per week.

Qualifications

• Experience working with groups of children (teaching, tutoring, coaching, camp counseling, or similar).
• Ability to lead a class independently with a friendly, engaging style.
• Professional, positive demeanor and kid-friendly approach.
• Strong grasp of chess fundamentals and ability to explain moves and tactics.
• Reliable transportation and willingness to travel between schools.

Responsibilities

• Lead fun, interactive chess classes for 10–15 elementary students.
• Follow the structured curriculum to teach fundamentals and good sportsmanship.
• Maintain a lively, positive classroom environment.
• Travel to local school sites for each session.
• Arrive prepared, on time, and ready to engage students.

Skills

Teaching

Group management

Chess knowledge

Communication

Job description

Area: Weston, CT

Do you love chess? Do you enjoy working with kids?

Chess Wizards is seeking enthusiastic, reliable instructors to join our after-school enrichment program! If you can make learning fun, create a positive classroom environment, and share the magic of chess with elementary students, this is the perfect side-hustle.

Why Join Us?

• Competitive Pay: $50 - $75 per class (Typical class time is approximately one hour and thirty minutes which includes pre-class setup, instructional time, and post-class responsibilities)
• Flexible Hours: Teach a minimum of 1 class up to a maximum of 5 classes per week. The specific number is based on the availability of classes at local schools in your area. Classes are scheduled on weekday afternoons, with start times typically falling between 2:00 PM and 5:00 PM at various local schools
• Travel Compensation: Mileage reimbursement provided for trips over 15 miles one way (30 miles roundtrip), from your home or work location. Work locations are assigned by the manager based on available schools and classes in your area.
• Full training and ongoing support.
• Full curriculum and materials.
• Free chess classes.
• Opportunities for advancement.
• Work flexibility.
• Great company culture!

What You'll Do

• Lead fun, interactive chess classes for 10-15 energetic elementary students. Instructors should be comfortable guiding activities, keeping students engaged, and redirecting 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

What We're Looking For

• 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. We seek upbeat, engaging instructors.
• Professional, positive, and kid-friendly demeanor
• Genuine desire to be a positive role model and promote good sportsmanship
• Strong grasp of chess fundamentals. You should be 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. The specific number of classes depends on availability at local partner schools.
• Commitment to implementing school safety protocols to protect students’ well-being. Because you will supervise children independently, a strong record of reliability and strict adherence to safety and school policies is required.
• Strong punctuality and time-management skills

Location Requirement: This position is based in Weston, CT. Please note that relocation assistance is not provided. Candidates must be currently residing in the area or be willing to relocate at their own expense.

Chess Wizards is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or veteran status.