Demand for Penetration Testers Is Rapidly Increasing
We live in an era of persistent cybersecurity threats, from discussions around banning TikTok in the US to a video-phishing incident that cost tens of millions of dollars. Organizations of all sizes are clamoring for skilled penetration testers to help secure their networks, web and mobile applications, and APIs against unauthorized access. The global penetration testing services market is projected to nearly triple from 2023 to 2032 amid the escalation of cyberattacks, as well as industry countermeasures such as the anti-fraud credit-card handling standard, PCI DSS 4.0. Whether prompted by legislation or not, companies worldwide are seeing the need to shore up against vulnerabilities by reexamining everything from tech stacks to staff training policies.
Finding skilled pentesters remains challenging. Ethical hacking certifications can validate a candidate’s foundational knowledge, but further validation of a candidate’s skill set comes from real-world experience with vulnerability assessments, incident response, and application penetration testing. Many roles demand expertise in specialized areas such as social engineering, wireless network security, or automated pen-testing tools — the search for cybersecurity talent is certainly nuanced.
This guide brings clarity to the complexities of recruiting penetration testers, including practical steps for writing effective job descriptions and insightful interview strategies. By understanding the subtleties of this critical role, you can identify the right talent to protect your organization effectively.
What Attributes Distinguish Quality Penetration Testers From Others?
A penetration tester identifies and mitigates security vulnerabilities. Their primary responsibility is to simulate real-world attacks, uncovering potential weaknesses before they can be exploited by malicious hackers.
Effective pentesters have encyclopedic technical knowledge and show a markedly creative methodology in leveraging it. For instance, they approach web application testing knowing the standard OWASP guidelines, but their scrutiny of authentication mechanisms, session management, and API interactions will let them uncover flaws that may be invisible to automated vulnerability scanning tools.
However, automated scanners are a useful starting point. Hands-on experience both with proprietary vulnerability scanners like Burp Suite or Nessus and open-source tools like the Metasploit Framework, Wireshark, and Nmap is a given in the pen-testing space. Standout candidates will know reverse engineering techniques and how to use languages like Python or JavaScript to craft custom exploits on the fly.
Quality penetration testers don’t just find vulnerabilities — they prioritize vulnerabilities based on potential business impact, concisely articulating recommended remediation strategies to stakeholders. And since they don’t normally execute these strategies themselves, it’s critical they have a track record of excellent collaboration with security engineers and software development teams.
How Can You Identify the Ideal Penetration Testers For You?
The right penetration tester depends on your organization’s specific goals — and skill gaps. Maybe you already have in-house web application security pen-testing, but need a social engineering expert to regularly test your staff for policy compliance. Maybe your business is expanding into a new area, exposing it to unfamiliar cybersecurity requirements. Or maybe your company already has a solid cybersecurity team and would like to verify their efficacy.
Defining a scope will help you target candidates with the right expertise. For example, if your primary goal is assessing APIs, look for testers experienced in application security testing and OWASP standards. For mobile applications, you’ll want a candidate familiar with your app’s platform (e.g., iOS, Android, or both) and specialized tools like MobSF. If phishing is a concern, experience with social engineering simulations is a must. Additionally, auditing Linux or Windows servers can be quite different from each other — a strong background in your organization’s specific environment(s) is the only way to evaluate server configurations and permissions effectively.
Certifications—if relatively current—can help verify a pentester’s baseline knowledge and practical skills. The full landscape of certifications is beyond the scope of this guide, but it’s good to be aware of two in particular: OSCP (Offensive Security Certified Professional) demonstrates practical skills in penetration testing and exploit development, while CEH (Certified Ethical Hacker) is restricted to theoretical aspects.
But real-world experience in a similar technical context or past successes with ethical phishing (as applicable) are at least as valuable. The question is, how much experience is appropriate for the role you’re filling?
Junior penetration testers are best suited to tasks like routine vulnerability scanning, conducting security assessments under supervision, or assisting senior testers. They often have 1-2 years of experience and may need practice with more complex techniques. Their experience may also be limited to a specific area, like corporate firewalls, mobile apps, or a specific operating system. That can be appropriate — a freelancer specialized in hacking mobile apps may uncover just as much viable attack surface as a more experienced generalist — but only if their past experience is an exact match for the role.
Mid-level penetration testers can handle standalone assessments, including exploiting vulnerabilities in web apps and mobile applications. They generally have 3-5 years of experience and can often readily adapt to various scenarios, from auditing an organization’s social engineering resistance to testing for SQL injection vulnerabilities in a web app.
Senior penetration testers are security experts who design and execute comprehensive testing strategies. With over five years of experience, they often lead red-team exercises to test a company’s incident response and conduct advanced social engineering simulations, they are used to providing effective remediation guidelines with clear technical details.
How to Write a Penetration Tester Job Description for Your Project
The definitions of and delineations between “penetration tester” and “ethical hacker” continue to be a source of industry disagreement. Some experts simply use the terms interchangeably as we’ve done here. However, the choice between the two role names for your job description isn’t as important as being specific about the expected scope of work. In fact, the role you have in mind may include enough adjacent elements that a system security expert job description template might be a good starting point.
Be sure to clearly outline your organization’s needs. Specify whether you need expertise in web app penetration testing, wireless network security, or social engineering, and name any skill requirements related to frameworks, whether they’re general pen-testing ones (like PTES) or use case–specific (like PCI DSS). Highlight desired certifications and tools, and highlight not only the required years of experience but also how the role fits into the relationship with existing members of your team.
Include expected deliverables, even standard fare like providing detailed pen-testing reports, articulating remediation strategies, and collaborating with security professionals to implement solutions. But for candidates to best understand the role, be sure to include as much detail as possible about the expected types and scope of penetration testing itself.
Lastly, emphasize whether the position is full-time, freelance, or part of a broader security consulting engagement and to what extent remote work fits your policies. Clear job descriptions will save you time by attracting candidates who are better aligned with your objectives.
What Are the Most Important Penetration Tester Interview Questions?
It’s worth quizzing candidates on common security mistakes (for example, how they might exploit or patch various web security vulnerabilities) but don’t neglect broader discussions in gauging their ability to apply information security principles. The following are designed to enable hiring managers — with the aid of in-house security experts — to identify top talent.
What is your process for integrating automation into penetration testing?
Automation enhances the efficiency and consistency of penetration tests. Which tools does the candidate use for repetitive tasks, such as vulnerability scanning or code analysis?
Look for a clear understanding of where automation ends and manual testing begins, particularly for nuanced vulnerabilities like business logic flaws. Ask for examples of how they’ve adapted automation tools to a specific project, as well as examples of when they’ve created ad-hoc pen-testing scripts in languages like Python.
Can you walk us through a recent penetration test you conducted?
With this broad opportunity to showcase their methodology and communication skills, strong candidates will reference frameworks like PTES or OWASP’s WSTG, emphasize both systematic and adaptive application security testing, and discuss their tooling preferences.
A good answer will cover security measures that the candidate encountered — such as firewalls and intrusion detection systems — and how they were able to bypass them. It will also cover which security controls they recommended, such as applying patches, hardening configurations, or implementing network segmentation.
Consider it a yellow flag if a candidate fails to prioritize vulnerabilities based on real-world impact or to propose clear, actionable remediation strategies.
How do you approach testing legacy systems, such as outdated PHP applications?
PHP is still widely used, particularly in legacy systems, even though PHP 8.0 hasn’t been officially supported since late 2023. If your tech stack involves (or may involve) an outdated PHP deployment, it’s highly relevant to check your candidate’s familiarity with PHP-specific risk factors, such as the misconfiguration of the long-deprecated register_globals or the use of the weak session ID generation mechanism that was once PHP’s default. Ask candidates to recommend methods for hardening legacy applications; responses can include securing PHP configuration options, adding modern authentication practices like 2FA, and integrating tools like PHPStan into build processes.
This question can be easily adapted to other languages and frameworks, especially in any projects in your organization with an under-active maintenance schedule.
Why Do Companies Hire Penetration Testers?
Penetration testers are indispensable in fortifying an organization against cyberattacks. Their expertise in simulating real-world attack scenarios enables companies to not only prevent costly breaches but also to respond better to unexpected scenarios. Skilled testers ultimately help to safeguard sensitive data, ensure regulatory compliance, and maintain the trust of their stakeholders. With this guide’s insights, your business is ready to fortify its defenses in an increasingly hostile cybersecurity landscape.
