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 technical program management coach to work with students and professionals building careers in technical program management. This role includes teaching core skills in technical project management, agile methodology, scrum, stakeholder management, and resource allocation, as well as risk management and quality assurance, and helping students build these capabilities through consistent, practical skill building. Coaches also support the career side of the journey, including resume review, cover letters, LinkedIn review, interview prep, and salary negotiation, as well as promotion strategy, networking strategy, and freelancing for those pursuing independent work. Ideal candidates have professional experience in technical program management, prior coaching or mentoring experience, and a clear, structured approach to breaking down complex technical and organizational concepts. 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.