Leland is building the home for ambition in the age of AI. We connect people with the experts, programs, and communities they need to land the job, get into the school, or upskill for a world being rewritten by AI. We help businesses become AI-native through training, hiring, and infrastructure. Since our founding in 2021, we've helped tens of thousands of people reach their most ambitious goals and raised $19M from world-class investors. Ambition is sacred to us, and we've built a product that takes that seriously.

We're seeking an experienced Chess & Board Games Coach to work with players looking to sharpen their skills and improve their rating. This role includes reviewing and analyzing games, building a strong opening repertoire, and developing middlegame strategy and endgame technique. Coaches also help players strengthen tactics and calculation, improve time management and clock skills, and prepare for upcoming tournaments, all guided by a personalized rating improvement plan. For newer players, coaches support general exploration of the game to help them discover their interests and strengths. Ideal candidates have a strong competitive chess or board games background, prior coaching or teaching experience, and a clear, structured approach to helping players understand and learn from their games. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every player.

Why Leland?

• The chance to join a world-class team helping people achieve their career and educational dreams

• Work in a collaborative, high-energy environment where your contributions have a direct impact

• Operate in a fast-paced, AI-native environment

• We don't hire people who merely want to work for a great company; we hire people who want to make a great company

Leland is an equal opportunity employer. We encourage candidates of all backgrounds and demographics to apply.