Site Reliability & Engineering Coach

Department: Coaches

Location: Remote - USA

Employment Type: Contract

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 site reliability and engineering coach to work with students and professionals building careers in site reliability engineering. This role includes teaching core skills in site reliability engineering, system monitoring, incident response, performance optimization, and automation, 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, behavioral interview prep, and technical interview prep, as well as salary negotiation, promotion strategy, and networking strategy, along with freelancing for those pursuing independent work. Ideal candidates have professional experience in site reliability engineering, prior coaching or mentoring experience, and a clear, structured approach to breaking down complex technical 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.