Leland

CISSP Tutor

United States full-time Mid Salary not listed
full-time Mid level Technology & IT Curated
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About the role

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

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Mid
Technology & IT Operations Cissp Tutor Technology Mid level full-time

Likely questions

  1. Tell us about work you have done that is close to the CISSP Tutor role.
  2. How would you approach your first 30 days at Leland?
  3. Which of Operations, Cissp and Tutor have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Operations, Cissp and Tutor.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the CISSP Tutor role because I can bring practical experience in Operations, Cissp and Tutor, learn the team quickly, and contribute to the outcomes Leland needs from this hire.

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