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 CISSP Tutor to work with clients preparing for the CISSP exam while also building toward long-term careers in cybersecurity. This role includes helping clients master exam content across Security and Risk Management, Asset Security, Security Architecture and Engineering, Communication and Network Security, Identity and Access Management, Security Assessment and Testing, Security Operations, and Software Development Security, along with creating a tailored study plan and test prep strategy to build accuracy, pacing, and confidence leading up to exam day. Beyond the exam, tutors help clients apply these concepts to real career growth in cybersecurity, connecting technical knowledge to practical, real-world application. Ideal candidates hold the CISSP certification, prior tutoring, teaching, or mentoring experience, and a clear, structured approach to breaking down complex problems. Tutors 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.