AI Strategy & Transformation Expert

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 AI consultants, Heads of AI, and product or growth leaders driving AI initiatives to coach professionals and business leaders on how to adopt and scale AI within organizations. Coaches help mentees understand how to identify high-impact use cases, develop AI strategies, and lead successful AI transformations across teams and functions. Ideal candidates have experience leading AI strategy, implementation, or transformation efforts within companies or through advisory roles, and can translate that experience into clear, actionable guidance. 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.