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 service academies and ROTC coach to work with students preparing to apply to military service academies and ROTC programs. This role includes guiding students through school selection and application strategy, congressional nomination strategy, and DoDMERB medical review and waiver support, as well as candidate fitness assessment training to help students meet physical requirements. Coaches also support students with essays, recommendations, resume building, and highlighting extracurricular activities, along with interview prep and waitlist strategy. Ideal candidates have firsthand experience with the service academy or ROTC admissions process, prior advising or coaching experience, and a clear, structured approach to helping students present their strongest possible application. 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.