5 Golden Tips to Land Your First Job in Offensive Security

Starting a career in Offensive Security can be both exciting and overwhelming. From bug bounty hunting to penetration testing, mastering the skills needed can seem like a huge mountain to climb. But with the right approach, dedication, and a little guidance, you can break into this field and thrive. Here are five golden tips to help you get started!

Every expert starts as a beginner. Begin with the foundations — cybersecurity basics, common terminology, and core concepts. Platforms like TryHackMe are fantastic for this. They offer Cyber 101 courses, which cover essential cybersecurity principles, and even modules focused on the OWASP Top 10, a fundamental list of the most common web vulnerabilities. Understanding the basics is crucial to make sense of advanced concepts down the line.

Start here:
Pre Security

Cyber Security 101

Once you have the basics down, it’s time to practice. Again, TryHackMe is a great resource. Start with hands-on labs covering each of the OWASP Top 10 vulnerabilities, you can find them as part of the Junior Penetration Tester (JR PT) path on TryHackMe. Practicing hands-on will sharpen your skills and help you build a deeper understanding of real-world scenarios.

Hands-on labs for OWASP top 10

After gaining confidence in your skills and doing some rooms on TryHackMe, challenge yourself on Hack The Box. Here, the virtual machines (VMs) are more complex, and the learning curve steeper, so don’t be discouraged if you get stuck. The process of struggling through these challenges is where real growth happens. At the beginning, I highly recommend following IppSec’s video write-ups. IppSec’s breakdowns provide valuable insights into advanced techniques, cheat sheets, and tools that you can use throughout your career.

Another Youtuber you should follow and watch is John Hammond

Bug bounties are an excellent way to learn offensive security by seeing what real-world vulnerabilities look like. There are two parts to this tip:

4.1 Read Bug Bounty Reports on Bugbounty sites
Check out reports that other researchers have disclosed on platforms like HackerOne. For instance, if you’re keen to learn XSS (Cross-Site Scripting) techniques, try searching “HackerOne XSS report” on Google. Reading through these reports will teach you about different methods and creative approaches, giving you insight into the mindset of successful hunters.4.2 Start Trying Bug Bounties Yourself
When you’re ready, jump into bug bounty hunting. Begin with free programs where competition is lower, which is great for both learning and building your resume. Practical experience is essential, and participating in these programs will give you exposure to real-world applications and scenarios.

Finally, Capture the Flag (CTF) competitions are a fantastic way to further hone your skills. Focus on CTF categories that align with your interests — such as Web, Binary, or PWN — and study from write-ups for each challenge you attempt (or for old CTFs). Reading others’ write-ups allows you to see different approaches and gain insights into problem-solving techniques that you might not have considered.