How To Launch a Career in Penetration Testing

How To Launch a Career in Penetration Testing

Getting Started with Penetration Testing – The Ultimate Guide

What is Penetration Testing?

Do you ever wonder how hackers are able to pull off a cybersecurity breach? Have you noticed in the news how often people are being attacked? If you are interested in learning how they do it you could be a great Penetration Tester.

In order to be a good Penetration Tester or Pentester, you need to get in the mindset of the attacker. If you are driven not only by the curiosity of how networked systems function, but also by how threat actors are able to infiltrate and dismantle them then you should be a pentester.  Pentesting is the practice of testing a computer system, network, or web application to find and exploit vulnerabilities before attackers do.

Where to start on your penetration testing career path?

First, a student must determine a career path in the discovery phase. Ask yourself the following questions:
  • What do I like to do?
  • What do I hate doing?
  • What experience do I have in Information Technology?

In order to figure out the questions above try the following to help guide you:

  • Watch Youtube videos to help you determine a path.
  • Study different areas of security to find out what interests you.
  • Seek entry-level jobs to get your foot in the door. Don’t worry about pay grade.
  • Look at the job boards and learn what is needed to obtain a job in pen testing


Second, pick a path based on what you find.

Do a job search on what you want to set your goal on. Look at the job description to help you determine what areas to specialize in. It will help you know what certifications the job requires and what experience they ask for. Then you can look at our schedule of classes and get ready to practice to pass the certifications.

Laying the foundation

There is no single required skill set to be a pen tester but with the right mix of skills and opportunity, you could become one by cultivating the right skills and hustle.

Some of the soft and hard skills you need:

  • Strong networking skills. Many vulnerabilities are network-based and you will need to exploit those vulnerabilities and identify issues in order to fix them.
  • System administration skills. Understanding how computers, servers, and network appliances work and are configured is an important part of pen-testing.
  • Nix Skills. Many network security tools are Linux-based and getting comfortable with the Linux terminal will be beneficial.
  • Programming Skills. Scripting languages (e.g. Bash, Python, Perl, PHP, and Ruby) and languages common in web development (HTML, CSS, JavaScript, SQL, and ASP.NET) in particular can prove quite useful.
  • Automation Skills. Scripting languages help you automate tasks and hit the ground running with many tools. Web development languages get you familiar with a common attack surface.
  • Communication and Interpersonal Skills. Soft skills are a big part of the job so you are able to effectively craft social engineering attacks.
  • Lockpicking. Pen testers can benefit from physical skills like lockpicking.


Here are 4 quick steps to get started

  1. Learn to Differentiate Penetration Testing from Hacking
    Unlike hackers, penetration tester works under strict rules of engagement – You go into specific areas only, and have limits on your actions. The purpose is to discover weaknesses, not break into the system for its own sake. You are the professional here, and definitely one of the good guys. It would be helpful to take classes to get cyber certifications.
  2. Know the Threats in the Real-World & Learn the Strategies and Solutions to Prevent Them
    Having the right IT infrastructure is critical to strengthening the company’s security. There are three main classifications to prevent various forms of cyber attacks: hardware solutions, software solutions, and smart-thinking solutions.
  3. Understand the Tasks and Responsibilities Expected from a Professional Penetration Tester
    As a penetration tester, you will be the one who conducts the penetration test, creates one or more reports about your findings (vulnerabilities), classifies the severity of the risks (high risk, medium risk, low risk), and explains the reasons why these risks are vulnerable.
  4. Practice your Skills with Real-Life Scenarios
    The most effective way to learn penetration testing is to learn by doing and not by reading. Practice in a virtual lab and get experience so when you are on the hot seat in your real job you will be ready.

Recommended Certifications


Common Job Titles

  • Penetration Tester
  • Information Security Analyst
  • Security Analyst
  • Ethical Hacker

Networking is very important

We have a free Digital Natives Meetup group that has over 8,200 members. This group is a great place to meet other IT professionals and network. These free events could help you get your foot in the door. We have Meetups every month that cover the current topics and interests in the quickly changing machine learning/ artificial intelligence field. We have guest speakers that are full-time professionals who show cutting-edge technologies and will share their passions concerning the IT field with you.

Digital Natives LogoWe have a very popular Digital Natives Meetup and we cover these topics in-depth including launching your career in machine learning.

Practice, practice and practice your soft skills
There is no better way to get better at your skills than to practice. You can start with many free tools to get your feet wet. It is important to keep the drive to want to learn more and keep your skills up to date with the current trends.

Some places you can practice your tech skills:

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