MentorCruise
Ryan Wilson

Ryan Wilson

Senior AI Penetration Tester @ Microsoft Headquarters
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7+ Yrs Penetration Testing | MentorCruise Veteran | Former Mentee Turned Mentor
United States of America Active this month Usually responds in a day or two

Services

$110 / month

Helping aspiring and active security professionals build real-world pentesting skills.

2 calls per month (60min/call)

Unlimited Q&A via chat

Expect responses in 24 hours or less

Hands-on support

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About

Hi, My name is Ryan Wilson I am a Senior AI Penetration Tester at Microsoft Headquarters. Some of you may know me as I was featured in a article on MentorCruise maybe 6 or 7 years ago as I am a product of this awesome platform, as I went from professional basketball player to professional ethical hacker. I learned penetration testing via MentorCruise and now I am here to give back again on my second stint. I started pentesting in England, then I moved on to another fortune 500 company (Top 3 cyber insurance company in the world) where I built and developed their first ever Penetration Testing department from scratch as a Senior Pentester and a Manager. From there I then moved to Microsoft Headquaters back in the US where I am building out one of their orgs first ever AI Penetration Testing departments. In my free time I like to workout, spend time with my family and run my own one man company called RySec where I perform contract penetration testing for various companies and Indian tribes. As I stated previously I am here to give back for my second stint and provide the knowledge and skills that you aspiring Penetration Testers will need to obtain your first job. I look forward to working with you all.

Thanks,

Ryan Wilson

Get to know Ryan

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Skills

Penetration Testing IT Networking Coding Red Teaming Ethical Hacking Mentoring Risk Assessment Vulnerability Management Web Application Security API Security Testing Cloud Security Secure Code Review Wireless Security Social Engineering Drone Penetration Testing Infrastructure Penetration Testing Mobile Penetration Testing Robotics Penetration Testing AI Penetration Testing

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Notify me when Ryan has new spots

We will send you a quick email if Ryan has new open spots for mentorship, and only in that case!

What's included in the trial?

Every trial is a little different–here's what Ryan says about their trial:

We'll meet for a quick call (usually under 30 minutes) where we:
- Break the ice and introduce ourselves
- Discuss your goals and how I can support you
- Coordinate logistics like time zones, meeting frequency, and communication methods
- Share strategies and tools to help you break into cybersecurity faster than the typical 3–5 year path