Chess Instructor | Spring

Chess Wizards, Inc.; Gilroy (CA); On-site; USD 8,000 - 17,000; Part time

Benefits offered by this job

Competitive pay per class

Flexible hours

Mileage reimbursement

Full training and ongoing support

Opportunities for advancement

Job summary

Chess Wizards, Inc. is seeking enthusiastic instructors to lead after-school chess sessions for elementary students in Gilroy, CA. This side-hustle offers flexible weekday afternoon commitments, a structured curriculum, and ongoing support from a full training program.

You will teach 1–5 classes weekly, typically 2:00 PM to 5:00 PM, traveling to local schools. Mileage reimbursement applies for trips over 15 miles one-way, and you’ll join a supportive team with opportunities for advancement.

Qualifications

• Experience teaching or leading groups of children.
• Ability to explain chess fundamentals to elementary students.
• Reliable transportation and ability to drive between locations.
• Availability on weekday afternoons.
• Commitment to safety protocols in schools.

Responsibilities

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

Skills

Teaching groups of children

Engaging classroom presence

Punctuality and time-management

Reliable transportation

Job description

Location: Gilroy, CA.

Schedule: Monday - Friday 2:00 pm - 5:30 pm

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: $55–$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.

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

Required

• 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

Chess Wizards Instructors receive full training and ongoing support. Full curriculum and materials. Free chess classes. Opportunities for advancement. Work flexibility. Great company culture!

Location Requirement: This position is based in Gilroy, CA. 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.

Application Requirements

• Resume: Include a resume detailing your relevant experience, including working with children in educational, recreational, or mentoring settings, as well as any teaching, tutoring, or classroom experience.
• Questionnaire: As part of your application, you will be asked to complete a required questionnaire related to your interest in the role, your experience working with children, and your qualifications to teach chess, among other topics