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 experts in AI automation and agents to coach professionals across industries on how to build and apply AI in their work. Coaches help mentees learn how to design AI workflows, automate processes, and build agent-driven systems that improve productivity and unlock new capabilities within teams and organizations. Ideal candidates have hands-on experience building AI automations, deploying agents, and integrating AI into real business workflows or products. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver practical, high-impact coaching.

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.