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 private high school admissions coach to work with students and families preparing to apply to private secondary schools. This role includes guiding families through school selection and application strategy, coordinating school visits, and helping students prepare for testing and assessments. Coaches also support students with essays, personal statements, and letters of recommendation, along with highlighting extracurricular activities that strengthen an application. Additional support includes resume review, interview prep, waitlist strategy, and guidance on financial aid and scholarships to help families navigate the full admissions process. Ideal candidates have firsthand experience with private high school admissions, prior advising or coaching experience, and a clear, structured approach to helping students and families 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 family.

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.