Penetration testing careers

Pentesters must have a broad understanding of various cybersecurity tools, processes and protocols about networks, endpoints, hardware and more.

Although it’s not necessary, having a bachelor's degree or higher in computer science, cybersecurity or information security can give you a solid foundation and allow you to stand out from other candidates.

For the most part, pentesters need to develop their knowledge of computer systems and cybersecurity, as well as tackle a few more skills:

• Scripting languages such as Python, Java, BASH, Perl and Ruby
• In-depth understanding of various operating systems, including Linux, Windows and MacOS.
• Network security tools and processes
• Application security tools and processes
• Threat modeling experience
• Experience with remote access technologies
• Basic understanding of security assessment tools
• Experience with technical writing and documentation
• Working knowledge of cloud architecture and cloud security
• Cryptography and various encryption protocols
• Use various pentest management platforms

As a pentester, you'll rely on a variety of tools. The tools will differ depending on your role and responsibilities. Many are free:

• Kali Linux: Enables pentesters with over a hundred hacking tools to simulate real threats

• Wireshark: This is a safe tool that can be used to troubleshoot network performance issues and as a learning tool for cybersecurity professionals to better understand network traffic analysis

• Hashcat: A popular tool for pentesters, system admins, spies and criminals to crack passwords

• Nmap: This tool helps pentesters probe computer networks and discover hosts and services on a network

• John the Ripper: One of the first and most essential password-cracking tools

• Burp Suite: Carries out workflows using a hybrid of manual and automated tasks to perform penetration tests on web apps

• Hydra: This login cracking tool helps penetration testers gain unauthorized remote access using several attack protocols

• Aircrack-ng: Allows penetration testers to assess WiFi network security with a suite of monitoring, attacking, testing and cracking tools

• Nessus: An open-source tool that uses the Common Vulnerabilities and Exposures architecture to scan for vulnerabilities

• SimplyEmail: An open-source tool that enables penetration testers to perform email recon

• OWASP ZAP Proxy: This open-source web app scanner is perfect for experienced penetration testers and those still learning about application security

• Zmap: A super-fast network scanner specifically for internet-wide network surveys

• PowerShell: Used to build and test virtual networks and automate scripts and commands

• Metasploit: One of the most popular penetration testing tools that help find security issues, mitigate vulnerabilities and manage professional security assessments
• Nikto: A vulnerability scanner that scans web servers for dangerous files, outdated server software and cookies

In a nutshell, the team colors refer to the role of the team protecting against attackers:

• Red teaming: A group known as ethical hackers that play the role of a cyberattacker to provide security feedback to an organization
• Blue teaming: A group that defends against cyberattacks and responds to cyber incidents
• Purple teaming: Experts, usually outside consultants, take on red and blue team roles to provide custom, realistic assurance to the organization

One of the most common penetration tester career paths is pretty standard: a formal degree in an information technology discipline or cybersecurity, a job as a systems or network administrator, specialized ethical hacking training, and a transfer to a position in security.

However, penetration testers can follow unorthodox paths; some don't have formal degrees and start their careers thanks to skills they acquire independently and augment with cybersecurity training and certifications.

Many credentials are available for professionals. It is usually a good idea to start with a more general option like the CompTIA Security+, then progress to more specific programs like the Certified Ethical Hacker (CEH).

This vendor-neutral credential from EC-Council is often the first certification in a specialized ethical hacking career path. It sets the standard of minimum knowledge needed to excel in the profession.

Several certifications will help you start your journey to become a pentester or upskill during your career:

CEH: Tests knowledge in finding and exploiting vulnerabilities

CPT: Entry-level certification that tests the ability to apply knowledge and skills in practice

CEPT: Takes the professional to the next level and tests their ability to manipulate Windows, Linux, and Unix shellcode and exploit code

CRTOP: Candidates demonstrate their ability to perform a comprehensive red team assessment

GPEN: Involves assessing target networks, systems and applications to find vulnerabilities as required during a penetration test

CMWAPT: Focuses on Web application pentesting, like how to profile an application and look for weak areas

CompTIA PenTest+: Candidates demonstrate their ability and knowledge to test devices in various environments, including cloud, mobile, desktops and servers

ECSA: Addresses the methodologies and the framework in which testers move

OSCP: Certificate holders proactively test security measures, provide security solutions, network testing, and more

Read our popular top 10 penetration certifications article for more!

Learn more about the PenTest+ exam domains, requirements and tips on Infosec's CompTIA PenTest+ certification hub!

Infosec's CompTIA PenTest+ hub is a comprehensive source of articles, advice, FAQs and free and paid training and resources, both online and in person.

For example, Infosec provides a five-day Ethical Hacking Boot Camp that you can take live online or in person. And, if you've got the time and self-discipline, there's on-demand PenTest+ training.

Check out the hub linked above for more information.

Many entry-level pentesting jobs require candidates to have 1 to 4 years of experience in IT with a background in system, security or network administration/engineering on top of official certification in pentesting, ethical hacking or something similar.

Because of the range of expertise required for pentesters to hack into computer and information systems, high-level positions may require upwards of 3 to 10 years of experience in network penetration testing or vulnerability assessment.

That being said, many career and certification paths can lead to becoming a penetration tester. Every penetration tester's career path will look different depending on their skills and abilities, aptitude to learn, and commitment to understanding and adopting an ethical hacking mindset.

There are five popular penetration testing methodologies:

• Open-Source Security Testing Methodology Manual (OSSTMM) is based on a scientific approach with adaptable guides.
• Open Web Application Security Project (OWASP) is run by a community of cybersecurity professionals and accounts for logic errors as well as application vulnerabilities.
• National Institute of Standards and Technology (NIST) provides specific penetration testing guidelines for pentesters for improved accuracy.
• Penetration Testing Execution Standards (PTES) are designed to be a comprehensive and up-to-date penetration testing standard.
• Information System Security Assessment Framework (ISSAF) is another open-source pentesting guide that links different steps of the pentest process with relevant tools.

As hackers ramp up their attacks on organizations around the globe, penetration testers are in high demand. According to the Bureau of Labor Statistics, pentesters and information security analyst jobs are projected to grow 35% over the next decade. This growth rate is much faster than the average job growth in the U.S.

About 20,000 openings for pentesters are projected to be added annually through 2031. Many of those openings are expected to result from the need to replace workers who transfer to different occupations or retire. The skills gap also threatens existing pentesters and information security analysts. So if you want to get into cybersecurity careers like pentesting, now is a great time.

Overall, it’s expected that there will be a high demand for penetration testers moving forward. Cyberattacks are growing, and pentesters are needed to create innovative solutions that prevent hackers from stealing critical information.

The U.S. Army operates across several networks with countless IoT devices in use, not to mention the number of digital records and protected information stored within their databases. A data breach of this magnitude is a matter of national security.

The U.S. Army currently has a high demand for penetration testers. The United States Government recently released new cybersecurity guidance for government agencies that requires them to submit to regular penetration testing and to address discovered vulnerabilities. But even before this legislation, the U.S. Army has been known to hire and train penetration testers.

Here are some examples of U.S. Army jobs for penetration testers:

• Cyber Warfare Officer
• Cyber Operations Specialist
• Cyber Network Defender

There are numerous penetration testing organizations, consulting agencies, and service providers to look at when you’re ready to shift to pentesting in your career.

These range from small consultant shops to large organizations that may support dozens or hundreds of clients. They may also specialize in certain areas, such as DoD organizations or certain industry verticals.

"When it comes to testing applications for security vulnerabilities, terms are misused all the time," says Ted Harrington, #1 Best-selling author and Infosec Instructor, in his article What is penetration testing, anyway?

"If you don't realize it's happening, it can have dire consequences. Most people ask for penetration testing but are sold vulnerability scanning instead."

Vulnerability assessments and penetration tests are crucial cybersecurity practices that help ensure that networks and devices are secure. A few key differences set them apart and make them useful in different ways.

Vulnerability assessments are usually automated scans that search computer systems for known, previously discovered and reported vulnerabilities. On the other hand, a penetration test is where cybersecurity experts attempt to exploit weaknesses, known and unknown, in an environment.

Vulnerability assessments show organizations what known vulnerabilities need to be remediated. A penetration test searches for known and unknown vulnerabilities and attempts to exploit a system to provide organizations with the information they need to bolster their security posture.

There are several benefits of penetration testing:

Protect clients, partners and third parties: A security breach can affect the target organization and its associated clients, partners, and third parties working with it.

Helps to evaluate security investment: The penetration test will give us an independent view of the effectiveness of existing security processes, ensuring that configuration management practices have been followed correctly.

Security gives companies a competitive advantage: "When you properly secure your software system and then can prove it, you obtain a competitive advantage that helps you earn trust and win sales," says Ted Harrington, #1 best-selling author and Infosec Instructor.

A penetration test has five phases:

Reconnaissance: testers gather as much information about a target system as they can, such as information about the network topology, operating systems, applications, user accounts, and anything else that they can use to exploit the system.

Scanning: during this phase, testers use various tools to check network traffic and identify open ports and other potential entry points.

Vulnerability Assessment: this is when testers determine the risk of the vulnerabilities discovered during the first two phases.

Exploitation: now, the tester will attempt to exploit the target system by simulating a real-world cyberattack.

Reporting: The final phase is when the penetration tester prepares a document reporting the findings during each pentest stage.

Are you just starting your IT career?

Everyone starts somewhere! To become a pentester, you'll first want to develop a foundation of skills like programming, threat modeling, and cybersecurity in entry-level jobs.

Ready to advance your skills?

There are several certifications to choose from, and you get the added benefit of learning new skills throughout the certification training process.

Start with certifications that will allow you to achieve an entry-level cybersecurity position, and work your way up as you learn more about penetration testing and security.

Once you've got the knowledge you need to operate as a penetration tester, getting involved in the open-source community and getting to know other penetration testing professionals in the field is essential.

They can give you tips on where to apply, companies to work for, and maybe even help you get your foot in the door.

When you land an interview, you can practice with these 10 common interview questions for penetration testers.