Military Careers Coach

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 military coach to work with service members and veterans looking to grow their skills and navigate their careers, as well as individuals looking to break into a military career. This role includes guidance on military strategy, military training, combat tactics, and leadership development, as well as helping clients navigate veterans affairs and their transition or career path with resume review, interview prep, networking strategy, salary negotiation, and ongoing skill building. Ideal candidates have hands-on military experience, prior coaching or mentoring experience, and a clear, structured approach to helping clients grow both their expertise and their career. 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.