CISSP Tutor
at Leland
Leland is building the home for ambition in the age of AI.
Job Overview
Published
Sep 14, 2026
Expires
Dec 13, 2026
Source
Leland
Region
US
Type
Remote / Work From Home
Category
WFH
Job 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.
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.
Originally posted on Himalayas
Remote Work Guidelines & Career Insights
Practical advice for succeeding as a remote professional in this role.
Asynchronous Productivity
High-performing remote teams prioritize asynchronous communication. Document your progress clearly in tickets, maintain organized project repositories, and communicate status updates proactively without waiting for real-time meetings.
Home Office & Security
Ensure a private, quiet workstation with a reliable high-speed broadband connection (min 50 Mbps). Maintain compliance with employer cybersecurity policies by utilizing secure password managers, 2FA authentication, and authorized VPN services.
Resume & Application Tips
Tailor your CV specifically to the requirements of CISSP Tutor. Highlight quantifiable achievements from past roles (e.g. revenue growth, efficiency improvements, or software shipped) and showcase proven experience collaborating with remote teams.
Virtual Interview Prep
Test your video and audio hardware before virtual calls. Prepare concise STAR-format stories demonstrating how you manage time independently, handle conflicting priorities across different time zones, and solve complex problems autonomously.
Frequently Asked Questions
Key answers about the application process, remote setup, and compensation for CISSP Tutor.
Is the CISSP Tutor role 100% remote?+
Yes, this is a fully remote work-from-home position with Leland. You can collaborate asynchronously, manage project deliverables, and participate in virtual team meetings from your home office without daily commuting.
What qualifications and experience are needed for CISSP Tutor?+
Applicants are typically evaluated on relevant industry background, core capabilities, and self-management. Key requirements include strong English communication skills, independent problem-solving abilities, and familiarity with modern remote collaboration platforms like Slack, Zoom, and project management tools.
Who is eligible to apply for this job?+
This remote opening welcomes applications from US and eligible remote regions. Candidates must ensure they meet the work authorization, residency, or independent contractor criteria required by Leland.
What is the salary and benefits package for CISSP Tutor?+
The expected compensation for this role is competitive compensation aligned with global remote market standards. In addition to base compensation, remote positions often provide flexible working hours, home office equipment stipends, and professional growth opportunities.
How do I apply and what should I prepare for the interview?+
Click the "Apply Now" button on this page to visit Leland's official application portal. Tailor your resume to highlight relevant achievements, and prepare to discuss your experience working productively in an asynchronous remote environment.
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