Assistant Chess Instructor - Fall

Chess Wizards, Inc.; Los Gatos (CA); On-site; USD 1,600 - 9,000; Part time

Benefits offered by this job

Full training

Free chess classes

Advancement opportunities

Work flexibility

Great company culture

Job summary

Chess Wizards, Inc. is seeking enthusiastic assistant instructors for its after-school enrichment program in Los Gatos, CA.

You will help set up and run engaging chess classes for 15–22 elementary students, with support for individual or small-group practice and classroom management. Responsibilities include following the curriculum, promoting sportsmanship, and traveling to local schools to support sessions.

Qualifications

• Genuine interest in working with groups of elementary students.
• Experience (teaching, tutoring, camp counseling, or similar) is a plus.
• Ability to follow direction and support the classroom management.
• Professional, positive, kid-friendly demeanor.
• Genuine desire to be a positive role model and promote good sportsmanship.
• Strong grasp of chess fundamentals and ability to explain basic moves to children.

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 with piece movements and basic concepts.
• Support the instructor in guiding activities, keeping students engaged, and reinforcing positive behavior.
• Follow the structured curriculum and promote good sportsmanship.
• Manage a lively classroom with confidence and positivity.
• Encourage problem-solving, creativity, and critical thinking.
• Travel to various local school sites for each session.

Skills

Student engagement

Chess basics

Reliability

Time management

Transportation

Job description

Area: Los Gatos, CA

Please Note: This vacancy is designated for the Fall season. Our recruitment team is currently conducting interviews for sessions scheduled to start in late summer/early fall

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

Why Join Us?

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.

• Competitive Pay: $40 - $50 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.
• Skill Development: Excellent opportunity to gain hands‑on teaching experience

What You’ll Do

• 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

What We’re Looking For

Required

• 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, and fun sessions. We seek upbeat, engaging assistants who are eager to support the learning environment.
• 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, a strong record of reliability and strict adherence to safety and school policies is required.
• Strong punctuality and time‑management skills

Application Requirements

• 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

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

Location Requirement

This position is based in Los Gatos, 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.