The 2024 Pentesting Roadmap: From Beginner to Hired in 8 Steps
A beginner-friendly guide to fast-track your journey and master the skills needed to land a penetration testing job
Breaking into penetration testing can seem overwhelming — especially if you’re starting with no prior experience. I know this from personal experience. For me, penetration testing once looked like an impossible career to build. But what if I told you that there are shortcuts you could use to accelerate your journey? By leveraging weaknesses in existing penetration testers’ methods and personalities, you could go from a complete beginner to landing your first job as a penetration tester in 2025.
Whether you’re a student, career-switcher, or someone who’s simply intrigued by offensive security, this roadmap is designed to fast-track your journey.
First, let me address some misconceptions that I see show up all the time in guides like this, probably made by senior testers that don’t usually have the responsibility of hiring people, and that are victims of the weaknesses I will tell you how to leverage. What you want is to learn the “must-haves” as fast as possible, get a job in the field, and then get paid while learning the “nice-to-haves”. Those “nice-to-haves” could be important in the long run, but they are not essential to break into the field. Let me divide some examples into two groups for you:
You don’t need (nice to haves):
Previous experience in IT
You can build the necessary skills from scratch specifically for penetration testing, without needing a general IT background.Coding skills
While useful later on, they aren’t essential to get started. Focus on tools and methodologies first.Expensive certifications
Many entry-level jobs value hands-on experience over certifications. Save the costly ones for later when your employer covers the cost.A blog or YouTube channel
Sharing knowledge is great, but it’s not mandatory at all for getting your first job in the field.
You need (must haves):
A strong work ethic and persistence
Success in pentesting comes down to how dedicated you are to solving problems and continuing when the going gets tough.Flexibility and willingness to learn in-demand skills
Focus on areas where there’s a shortage, like cloud or OT security, to make yourself more valuable quickly.Soft skills as well as hard skills
The ability to communicate your findings clearly, both in writing and presentations, is crucial — clients need to understand your discoveries.Patience and willingness to do the work
Don’t just rely on guides and write-ups, do your own work.
So, the good news? You don’t need to be a coding genius or have years of IT experience to get started. By focusing on the right skills, certifications, and practical experience, you can stand out and land your first job as a penetration tester in under 12 months. This guide will show you how in 8 simple steps.
Step 1: Dedicate Yourself to the Journey
None of this will work unless you commit. The most important aspect of your journey is your dedication and persistence. This journey will take time and hard work, but if you stay committed, the results will follow. This article is not about how to stay motivated and dedicated, so I won’t spend much time on it.
If this is a challenge for you, I suggest reading about techniques for productivity, or watching videos on motivation. Find what drives you and commit to seeing this through. This is entirely in your own hands, and up to you to promise yourself to keep up the work. Stay dedicated, and you will see good results in the long term.
Step 2: Understand the Goal of Penetration Testing
To understand what it takes to enter this field of work, it is crucial to understand what penetration testing actually involves. At its core, Penetration Testing is about problem-solving. You are trying to make applications do things they shouldn’t do, think of it as reverse troubleshooting. You want to provoke errors, and then try to understand why those errors happened to exploit them. This is why Hack The Box is such a popular platform among aspiring penetration testers. It’s an unforgiving environment designed to throw hard problems at you without any mercy, expecting you to work hours without any progress, just hoping that you are on the correct path.
This is very similar to real penetration testing. Often, you don’t even know if the solution to your problem (a vulnerability), even exists. This makes penetration testing as much about methodical exploration as it is about technical skill. Your job is to find and exploit vulnerabilities in systems, networks, and applications — mimicking an attacker’s approach. The goal is to identify weaknesses before they are used maliciously.
Nobody is paying you to hack their systems. They are paying you to find and report security flaws, explain the potential risks, and offer guidance on how to mitigate those weaknesses. You are there to help companies improve their security posture and ultimately protect their business assets.
This is a crucial distinction: A penetration tester is not a hacker. Understanding the difference is important. While both roles involve finding system vulnerabilities, the penetration tester has an additional responsibility in effectively and professionally present the problems they uncover, and the solutions to them.
This additional responsibility is in my opinion more important than the technical part. Your expert hacking skills provide no value if your customer doesn’t understand what risks your findings expose their companies to.
Step 3: Choose your specialization
Yes, you read that right, I recommend you specialize while having little to no general knowledge about penetration testing. While this may seem counterintuitive, building expertise in one area can be your fast-track to landing a job, as long as this area is in high demand. Penetration testing is a fast-evolving field. Certain areas of infrastructure and types of applications are always in greater demand than others. Choose one of those areas. This means that your specialization will NOT be Active Directory, no matter how much you want it to be.
Do some research by looking at job postings. What are people and companies around you actively searching for? This can vary depending on various factors, but here are some guesses you can take inspiration from:
Web Application Penetration Testing
Always in high demand, and still a growing field. This is also one the areas that have the closest to a standardized testing methodology due to the OWASP framework, making it simpler to learn.Cloud and Penetration Testing (Azure, AWS, GCP)
This is still a relatively new field, and many penetration testers shy away from it because learning new areas of expertise is hard. As a beginner, you don’t have this limitation, and jumping in at the newer areas of pentesting could be a great way to be valuable fast.OT/IoT Penetration Testing
We are getting rather niche here, but this is absolutely a field where companies could be desperate to hire someone that even has a small amount of knowledge. A large part of penetration testers dislike OT/IoT testing, even though it is growing at a high pace due to OT systems being exposed to cloud integrationsAPI Testing, Container and Kubernetes Testing, Social Engineering, Physical Testing, Mobile Application Testing
Each of these fields are situational and can be in high demand, depending on trends, your location, or industries in your area.
Take some time to research which path aligns with both your interests and the job market around you.
Step 4: Get Hands-On Experience
Personally I would rank the hierarchy of experience like this:
Work experience > Bug Bounties > Certifications > HTB/Tryhackme/otherIn short, real-world experience carries the most weight, but bug bounty experience is not far off. There are plenty of ways to gain practical, hands-on experience that will help you stand out.
Practice in Real-World Simulated Environments
Tools and platforms like TryHackMe, Hack The Box, and VulnHub provide real-world simulated environments where you can practice what you have learned. While TryHackMe is a great learning platform for learning new things, Hack The Box is a great platform for training your testing methodology. If you go the route of web application testing, the “Web Security Academy” from PortSwigger and their tool Burp Suite are all you need in the beginning, and amazing free resources.
Bug Bounty Programs: Your shortcut to Real-World Experience
If you want to impress potential employers, bug bounty programs are the best option. To me, bug bounty experience is almost as good as work experience, and it will make you stand out like a rockstar compared to most other people applying for entry-level jobs in penetration testing.
Bug bounty programs are more attractive to employers than certifications, if a pentester is involved in the hiring process. Platforms like HackerOne and Bugcrowd allow you to hunt for vulnerabilities in live systems — And you might even get paid for it! More importantly, bug bounty experience shows initiative above and beyond what one would expect of a beginner, and it proves that you can find actual real vulnerabilities.
I know that bug bounty programs seem scary and too difficult for most testers I have talked to, but I would recommend that you try it out. I would actually recommend spending all the energy you wanted to use on learning platforms like HTB on bug bounties instead. Especially for web application testing. Do a category of labs in the PortSwigger Labs (Web Security Academy), and then apply that knowledge to your testing.
Step 5: Choose the Right Certifications, if any
Let’s be clear: Contrary to popular belief, certifications are still valuable, but you don’t need a wall full of them to get started in penetration testing. You might not even need a single one to land your first job, but they will give you an edge.
Look for a cheap, respected certification within the specialization you have chosen. For example the “Burp Suite Certified Practitioner” for web application testing, or “Attacking & Defending Azure AD Cloud (CARTP)” for Azure testing.
Yes, Offensive Security Certified Professional (OSCP) is a very impressive certification to have for a beginner, but it will probably be very hard to attain in a short amount of time, and it will also not give you expertise in any one area. When it comes to certification there are some newer ones that I know little about, like the one offered by Hack The Box, so do the research yourself to see what is worth it. DO NOT spend all your money and time on collecting expensive certifications. Your job will pay for you to take those later on.
Pro Tip: Work experience trumps certifications. While these certifications will open doors, nothing beats real-world experience, for example from bug bounties, when you’re looking to get hired.
Step 6: Develop Crucial Soft Skills
Among penetration testers, technical prowess is highly respected. Because of this, many pentesters overlook the importance of soft skills, and that’s a big mistake. Being able to find vulnerabilities is only half the job. The ability to effectively communicate your findings and their mitigation steps is just as important. While those latter skills may be overlooked by the average penetration tester, they most likely will not be overlooked by the team lead or senior tester that interviews you for the job. Employers are always on the lookout for pentesters who can present their discoveries, write clear reports, and support the customer. These skills will not only make you a better penetration tester, they will also help you perform better during job interviews.
Here are the key soft skills you should develop:
Presentation Skills: Be confident in delivering your findings to both technical and non-technical audiences. Take some notes from developers and try to present your findings to a rubber duck. This will both help your presentation skills, but also help you with knowledge retention.
Writing Skills: The ability to write detailed, clear, and actionable reports is crucial. Your report may be the only thing the client reads. And again, know your audience. You should know how to write about your findings both to technical and non-technical people.
Meeting Preparation: Always be prepared for meetings and discussions. Prepare for the questions that may be asked, and how to answer them.
And always remember this: You have fun while doing the testing, but you get paid for the report and presentation.
Soft skills are not just a “nice to have”, they are critical to your success. This is your easiest way to stand out compared to other applicants. Every hour spent on working on this will pay double what the hours honing your technical skills will.
Step 7: Overprepare for the interview process
Preparing for a pentesting interview is often underestimated, and many candidates walk in without having prepared specifically for a job interview at all. The technical know-how that got you to the interview is only part of the equation, now you need to show you can apply that knowledge under pressure.
Different companies have different methods of doing pentest interviews, but here are some of my experiences:
Walking through a typical pentest
This is the methodology I like to use myself. I typically don’t care about specifics like tool names and so on, but rather that you can explain to me what your testing methodology looks like. I will expect everything from the presale process to the post-test presentation. Especially the phases outside of the technical testing itself is where you can impress at the entry-level. For example, be prepared to walk through what your methodology for testing a web application looks like.Specific tools and their uses
You could also be quizzed on specific popular tools like Nmap, Burp, Metasploit and so on. In my opinion, a better way for the interviewer to do this is to ask you to talk about the tool you use for things like vulnerability scanning, tunneling, handling shells and so on.Scenario-based questions
The interviewer could ask you to explain how you would perform a test of a blog that has a functionality to leave comments, or how you would mitigate an SQL injection vulnerability.Whiteboard session or live demo
The interviewer could give you a problem on the spot to solve, either using a whiteboard or an actual live demo where you demonstrate your methodology. Don’t get too stressed here, your explanation of your process is just as important as getting the flag in the end.CTF to solve at home
You could be sent home with access to a Lab they want you to solve over a couple of days or a week.
My biggest tip here is to calm down and do many interviews. Make sure that your first interview is not for the job you want the most, as you will probably perform much better after a couple of tries.
Step 8: Start applying, and not only to the dream job
Once you’ve built up your skills and gained some experience, it’s time to hit the job market. But here’s the key: don’t limit yourself to only applying for your dream job. While it’s great to have long-term career goals, focusing solely on landing the perfect position can delay your entry into the field.
Why You Should Cast a Wide Net
Entry-level pentesting roles can be highly competitive, so it’s important to apply to a range of positions, even if they aren’t exactly what you envisioned. Roles such as junior penetration tester, security analyst, or vulnerability assessor can provide valuable hands-on experience and help you get your foot in the door. Many of these jobs can serve as stepping stones, allowing you to build your portfolio, learn on the job, and advance toward your dream role.
Don’t Dismiss Smaller Companies
Sometimes, the big-name companies are where everyone’s applying. But don’t overlook smaller firms or startups. They often offer more hands-on experience, quicker growth opportunities, and may even expose you to a wider variety of tasks. You might find that a role at a smaller company can help you develop a more diverse skill set and get noticed faster. One thing you do want, however, is someone that is much better at you already working at the company. This way you will learn faster, and have something to replicate and reach for.
Remember: your dream job will still be there a couple of years from now, but getting relevant experience now will help you land it faster.
Conclusion: Fast-Track Your Way to Success
Becoming a pentester in less than 12 months is entirely achievable with the right approach and commitment. By following this roadmap, mastering essential technical skills, earning key certifications, gaining hands-on experience, and honing your soft skills, you’ll position yourself strongly for your first pentesting job.
But remember, the journey doesn’t stop at landing the job. The field of penetration testing is fast-paced and ever-evolving, so continuous learning and adaptation are essential to long-term success. Stay curious, stay updated on the latest trends, and never stop improving. With this mindset, you’ll not only secure your first role, but you’ll thrive in this industry.
