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 medical residency & fellowships coach to work with applicants preparing to apply to residency and fellowship programs. This role includes helping clients with specialty selection, program selection, and application strategy, developing their personal statement and essays, preparing for interview prep, guiding letters of recommendation, and navigating match strategy, clinical rotations, licensing, financial aid & scholarships, resume review, and waitlist strategy. Ideal candidates have hands-on experience with the residency or fellowship application and match process, prior coaching or mentoring experience, and a clear, structured approach to helping clients present their strongest candidacy. Coaches set their own hours and rates, host sessions virtually, and partner with our team to deliver a high-quality, supportive experience for every client. 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.