Getting a Penetration Testing Job

Robert Scocca
12 min readFeb 22, 2022

Only 1 year IT experience and fresh out of college, this is my story of how I became a penetration tester. About all the jobs, courses, certifications, and projects I worked on leading up to my current employment. The purpose of this article is to be a reference for other aspiring penetration testers and IT security professionals.

For years, I’ve wanted to be a penetration tester. It is the sexiest profession in the IT security world. What is cooler than hacking and getting paid for it!? Coming out of high school, I read a news story saying something to the effect of ‘cyber security jobs will make you loads of money, dude’. I didn’t really know what to do with my life at this point, so this article was all it took to push me in the cyber security direction. Apparently, reading a news story is a common way to get into ethical hacking.

Tech blog posts about folk’s journeys to getting the career they want is one my favorites to read. It’s inspiring to read about someone plotting out their goals and achieving them. Also, reading about their paths is useful as reference in thinking about your own next career move, what project to work on next, what technical skills to hone in on.

Passion for Hacking

The most valuable attribute to have in any career is passion for what you’re doing. If you’re not interested in your work, what’s the point?(Yes, I know, money, but hopefully you have the luxury of working towards monetizing something you enjoy.) Once you have passion, the desire to learn will follow. Passion can’t be taught. You can’t force someone to be interested in something. I exploited my passion in cyber to chase a career in pentesting. Employers look for this passion and hire people that have it. A company can teach skills, but they can’t force you to be interested and take your work seriously.

IT Security is not a career you can just pick up a degree for and be set for life. Cybersec is extremely vast in subject matter and constantly changing with technology. You need to be an eternal student to be a competent professional. To build your resume for a decent cyber security job you may…

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