Lead Teacher Trainer I Fall

Chess Wizards • Los Gatos, CA

15d • Onsite

About The Position

Chess Wizards’ Lead Teacher Trainer helps align instructor performance with customer expectations and is a stepping stone toward future management opportunities. In addition to teaching chess classes, the role assists with training, developing, coaching, and evaluating instructors. Lead Teacher Trainers set an example for the experience provided to students, parents, school administrators, and colleagues, in alignment with the Chess Wizards Mission Statement.

The position involves leading fun, interactive chess classes for groups of 10–15 elementary students. Classes generally begin after school dismissal, typically between 2:00 p.m. and 4:00 p.m. Teachers arrive 15 minutes before class to prepare and remain until students have been safely dismissed to an authorized adult. Typical paid class time is approximately 90 minutes, including setup, instruction, and post-class responsibilities; longer official classes receive additional pay. Trainers may also be the first choice for day-camp assignments during winter, spring, and summer breaks.

The role supports the local Area Manager by helping ensure programs and instructors receive management visits for coaching, customer conversations, and quality control. Trainers communicate regularly with their supervisor, complete class evaluation reports, engage with school administrators and parents during site visits, gather feedback, assist with customer service and marketing, and help troubleshoot program challenges.

This position is based in Los Gatos, California. Candidates must live in the area or be willing to relocate at their own expense; relocation assistance is not provided. Chess Wizards provides full training, ongoing support, curriculum, and materials.

Requirements

• At least 2–3 years of experience working with groups of children in teaching, tutoring, coaching, camp counseling, or a similar setting.
• Strong grasp of chess fundamentals, including the ability to explain piece movement, basic strategy, and simple tactics clearly, confidently, and in an age-appropriate way.
• Ability to guide activities, keep students engaged, and redirect behavior when needed.
• Reliable transportation to reach classes throughout the metropolitan area.
• Availability during after-school hours at least four days per week.
• Must currently reside in the Los Gatos area or be willing to relocate at personal expense.

Nice To Haves

• Availability five days per week during peak fall, winter, and spring program weeks.
• Teaching, tutoring, or classroom experience.
• Experience working with children in educational, recreational, or mentoring settings.

Responsibilities

• Lead fun, interactive chess classes for groups of 10–15 elementary students.
• Assist with training, coaching, development, and performance evaluation of instructors.
• Assist the local Area Manager in ensuring programs and instructors receive management visits for coaching, customer conversations, and quality control.
• Help troubleshoot and resolve program challenges.
• Complete class evaluation reports and discuss them with the supervisor.
• Communicate daily with the supervisor during the programming season.
• Speak with school administrators and parents during site visits, gather feedback, and assist with customer service and marketing efforts.
• Arrive on time, prepared, and ready to engage students, and remain until students are safely dismissed to an authorized adult.
• Maintain professional communication best practices.

Benefits

• Competitive pay of $65–$85 per class.
• Mileage reimbursement for trips over 15 miles one way (30 miles roundtrip) from home or work location.
• Full training and ongoing support.
• Access to a complete curriculum and materials.
• Free chess classes.
• Opportunities for career advancement.
• Flexible work schedules.
• Fantastic company culture.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed