Start a Penetration Tester Career

This article is part of an article series about my personal experience and career in the penetration testing and security field.
Part 1: Start a Penetration Tester Career (this part)
Part 2: From Beginner to Expert as Penetration Tester
Part 3: Working at a CERT and shifting to Technical Lead

From Administrator to the first Penetration Tester Job

I am sharing this because people ask me often about how to get into information security and how to improve a career. In this post, I describe my personal career and learning path including recommendations for books and more learning material. This may not be perfect to other people, for me it just worked. In later posts, I will give some recommendations for a more idealized learning path for different careers, for example as a penetration tester or a forensics specialist.

When I was working as an administrator back in 2011, I began starting to think about how I might change my career. My job back then included some Windows and Linux administration as well as some PHP and VBA coding. Further, I had coding skills in C and Java. In October 2012 I started my first job as penetration tester.

At this time, it was not clear to me whether to go more into depth as a network admin or to security. Since it seemed to be a good idea to have some networking skills, I started to work out a plan for getting the CCNA. 

Network skills
I started with the Mikrotik MCNA, since there was a training possibility in the town where I lived, I only used the training material offered by this course, but if you want more information have a look at the official Mikrotik page: https://mikrotik.com/

Then CompTIA Network+ followed. For the test preparation, I relied on two sources. The first is the free video series from professor Messer, these are excellent and I used to make notes about the content and reviewed them before a new training session. After the videos, I bought the book
Mike Meyers’ CompTIA Security+ Certification Passport” that included some example questions for training.

The CCNA was my first “bigger” certification and I remember that I put a lot effort in it, for example I bought a bunch of old switches and routers for a home lab. This was not necessary, but of course, it added some fun at this time. Much easier is to use simulation software for doing some labs.

Besides my own experiments, I worked through the book CCNA Routing and Switching Complete Study Guide. The certification at this time included not only the multiple choice tests, but also lab exercises.

Security skills
Because it became clear to me that I wanted to go into Security in my career, I started the CompTIA Security+ certification. As like for Network+ I used the Professor Messer tutorials and the book Mike Meyers’ CompTIA Security+ Certification Passport. 

I wanted to work as a penetration tester; I decided to do the OSCP certification and I am happy I did choose it over the CEH. Here is my review in German, more reviews in English here.

I made the certification in 2012, and nowadays I do not think that you must have an OSCP necessarily, although I strongly recommend it. It is a great certification and it surely helped me especially when it comes to attitude, endurance and patience. However, it can be a frustrating experience and if you do not have enough time or motivation, it will be hard. For me it was fun!

During the OSCP preparation, I bought two books:
–      The German book “Hacking mit Metasploit” (Hacking with Metasploit) by Michael Messner, which helped me a lot because it also introduced some Exploit Development and Client Side Attacks.
–      Hacking: The Art of Exploitation by Jon Erickson 

After the OSCP, I was lucky to find my first Job as a penetration tester.

Besides the certifications I also did a course at coursera “Webapplication Engineering” which I liked but it seems it was not continued.

Together with a friend we published an article in the German issue of the pentest magazine about pivoting, which was good having it on my CV for the first job in the field.

Conclusion
If you want a job in this field, the most important thing for me is to show that you are motivated. Nowadays I had some job interviews “on the other side” from the perspective of an employer. So besides qualifying with certifications and courses you should consider:

  • Start your own blog
  • Start your own projects on github
  • Contribute to projects
  • Networking (when I looked for my first job as a penetration tester I used Xing and wrote to company owners and asking for a job, which was successful) 
  • Consider publish articles on platforms like Xing, LinkedIn, magazines etc.

In the next part, I will go from starting the first job to going for expert level.

5 thoughts on “Start a Penetration Tester Career”

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