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 Athlete Career Transition Mentor to work with former professional athletes transitioning into their next career. This role includes guiding athletes through career transition and job search strategies, as well as building leadership development and personal branding for life after competition. Mentors also support professional networking, resume review, and interview prep, along with financial planning and continued endorsement and sponsorship strategy as athletes navigate this new chapter. Ideal candidates have professional or elite athletic experience, prior mentoring experience, and a clear, structured approach to helping athletes translate their skills and identity into a new career path. Mentors set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every athlete.

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.