[Hiring] CISSP Tutor @Leland

Role Description

Leland is 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 various domains:
• Security and Risk Management
• Asset Security
• Security Architecture and Engineering
• Communication and Network Security
• Identity and Access Management
• Security Assessment and Testing
• Security Operations
• Software Development Security
• Creating a tailored study plan and test prep strategy to build accuracy, pacing, and confidence leading up to exam day.
• Helping clients apply these concepts to real career growth in cybersecurity, connecting technical knowledge to practical, real-world application.
• Setting own hours and rates, hosting sessions virtually, and partnering with our team to deliver a high-quality, supportive experience for every client.

Qualifications

• CISSP certification
• Prior tutoring, teaching, or mentoring experience
• Clear, structured approach to breaking down complex problems

Benefits

• 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 hire people who want to make a great company

Company Description

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.