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 poker coach to work with players looking to sharpen their strategy and improve their results. This role includes teaching game theory and strategy, hand reading, and bankroll management, as well as guidance tailored to cash game strategy or tournament strategy depending on a player's focus. Coaches also help players strengthen their mental game and tilt management to stay disciplined and consistent at the table. Ideal candidates have significant competitive or professional poker experience, prior coaching or mentoring experience, and a clear, structured approach to helping players break down complex strategic decisions. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every student.

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.