Jr Pentester Roadmap

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roadmap

Breaking into the world of pentesting can feel overwhelming, but with the right roadmap, you can navigate the journey with confidence. Whether you’re starting from scratch or pivoting from another IT role, this guide will help you focus on the key areas that matter most.

Here’s the roadmap I recommend:

Build Your Fundamentals

Before diving into pentesting, it’s essential to have a solid foundation in IT, Networks, and Security.

Consider pursuing certifications like:

  • CompTIA Network+
  • CompTIA Security+ or (ISC)2 CC
  • Cisco’s CCNA

These will equip you with the core knowledge needed to understand the environment you’ll eventually be testing.

Gain IT Experience

Experience in an entry-level IT role is crucial. Look for positions in Managed Service Providers (MSPs) or Managed Security Service Providers (MSSPs). These environments expose you to a wide range of systems and scenarios, helping you solidify your knowledge.

While gaining experience, also focus on hands-on practice. Start with beginner modules on platforms like:

  • Hack The Box Academy
  • TryHackMe

Additionally, delve into web application security through resources like:

  • PortSwigger’s Web Security Academy (cover all apprentice and practitioner labs)

Get comfortable with Linux terminal commands and tools like Nmap, Burpsuite, Nuclei, Hashcat, WFuzz, Metasploit, and SQLMap.

Join a CTF Team

Capture The Flag (CTF) competitions are a fantastic way to learn by doing. Find a CTF team where you can collaborate with more experienced testers. Some excellent CTFs to explore include:

  • SquareCTF
  • PicoCTF
  • GoogleCTF
  • Advent of Cyber (THM)
  • KringleCon (SANS)
  • Deadface CTF
  • NahamCon CTF

Being part of a team helps you learn faster and stay motivated.

Get Certified & Document Your Journey

As you build your skills, certifications will help validate your knowledge. Look into hands-on pentesting certifications like:

Document everything you learn. Share your experiences, write detailed reports on the challenges you overcome, and showcase your progress online. This not only reinforces your learning but also builds your reputation within the community.

Network with the Community

Networking can’t be overstated. Many people land pentesting roles through referrals rather than cold applications. Engage with the cybersecurity community on platforms like LinkedIn, Twitter, or relevant forums.

  • Connect with peers and industry experts.
  • Join online groups and participate in discussions.
  • Attend cybersecurity conferences (even virtual ones) to broaden your network.

Don’t forget to apply to junior roles, and most importantly, don’t give up. Persistence is key in this industry.

Final Thoughts

Becoming a junior pentester requires dedication, continuous learning, and an active presence in the cybersecurity community. Follow this roadmap, work on these areas simultaneously, and stay consistent in your efforts.

Success in pentesting, like in any challenging field, doesn’t come easy—but with the right approach, it’s entirely achievable.


If you’re interested in conducting a security review or penetration test, feel free to reach out to us. We’re here to help you secure your environments effectively.