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 Cybersecurity Coach to work with clients looking to break into or grow within cybersecurity roles. This role includes teaching core cyber security strategy, network security, and incident response skills, as well as helping clients build strong risk assessment, security auditing, and vulnerability management practices. Coaches also support clients on the career side, offering resume review, LinkedIn review, and cover letter guidance, along with behavioral and technical interview prep tailored to cybersecurity roles. Additional support includes networking strategy, salary negotiation, promotion strategy, broader skill building, and guidance for those pursuing freelancing opportunities in the space. Ideal candidates have hands-on experience in cybersecurity (as a security analyst, engineer, or industry professional), a strong track record of protecting systems and responding to threats, and a clear, structured approach to coaching clients through both technical and career growth. 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.