Chess Instructor Jobs in Santa Cruz, CA (NOW HIRING)

Regional Support Chess Instructor

Location: San Jose and South Bay, CA

Pay: $30 to $34 per hour

Job Type: Part-Time | In Person

Join Our Leadership Team

We're looking for a dependable Regional Support Chess Instructor to support our growing after-school programs throughout the South Bay.

This role is designed for instructors who enjoy taking on additional responsibility and are interested in growing with Yes For Chess over time. Rather than being assigned to just one or two schools, Regional Support Instructors help support multiple South Bay programs, assist with launching new school locations, provide classroom coverage when needed, and help ensure students receive a consistent, high-quality experience across our programs.

This position is ideal for someone who enjoys variety, thrives in different classroom environments, is comfortable traveling throughout the South Bay, and wants to play an important role in a growing organization. Higher hourly rate is offered in recognition of the flexibility, reliability, and travel this role requires.

What You'll Do

Teach engaging after-school chess classes

Support multiple South Bay school locations throughout the week

Provide classroom coverage when needed

Help launch new school programs.

Build positive relationships with students, schools and families

Communicate professionally with the office team

Deliver a fun, consistent classroom experience

What Makes This Position Different?

Regional Support Instructors play an important role in helping our South Bay programs succeed. Because of the flexibility and reliability this role requires, they are often the first considered for expanded opportunities as the company grows, including additional teaching hours, online coaching, tournaments, curriculum projects, mentoring new instructors, and future operational responsibilities.

What We're Looking For

Basic chess knowledge is requiredyou don't need to be a chess master.

We're looking for someone who:

Is confident with the basic rules and fundamentals of chess and enjoys teaching beginners.

Can comfortably teach elementary students who are learning the game.

Is reliable, organized, and communicates well.

Is friendly, patient, and energetic.

Is comfortable leading an elementary classroom independently.

Is willing to travel throughout the South Bay.

Wants to grow with the company.

Enjoys making a positive impact on children.

Experience teaching, tutoring, coaching, leading camps, working in childcare, or supporting youth programs is a strong plus.

All offers of employment are contingent upon the successful completion of a background check.

What We Offer

$30 to $34 /hour teaching rate

Guaranteed teaching schedule of at least four weekday afternoons per week (approx. 69 teaching hours).

Mileage reimbursement for qualifying travel is available

Ongoing coaching and support

Structured curriculum

Supportive team environment

The Ideal Candidate

This position is perfect for someone who enjoys working in different schools, adapts quickly to new environments, and likes having a variety of teaching assignments.

If you're dependable, enjoy working with children, and are looking for a flexible, higher-paying part-time role, we'd love to hear from you.

Teaching Region

Primary teaching assignments: San Jose, South San Jose, Santa Clara, Milpitas, and Sunnyvale

This position requires reliable transportation and regular travel between schools throughout the South Bay. A personal vehicle is strongly preferred.

Schedule

Guaranteed minimum of 4 afternoons per week (approximately 79 hours per week).

MondayFriday afternoons

Classes generally begin between 2:30 PM and 3:30 PM

Most teaching assignments last approximately 90 minutes

Training begins in August

Teaching begins in September

Additional teaching opportunities may become available as our programs grow.

About Yes For Chess

Yes For Chess is one of the Bay Area's longest-running after-school chess programs. For over 18 years, we have introduced thousands of elementary students to chess through fun, engaging, and educational after-school classes.

Our goal isn't to create chess masterswe help students build confidence, critical thinking skills, and a love for learning through chess. We're proud of our supportive team culture and invest heavily in training, coaching, and helping our instructors succeed.