Penetration Tester Career Path: Key Steps and Opportunities

Penetration Tester Career Path Featured Image

What does the penetration tester career path look like for you?

Are you looking to step into the role of a pentester, or are you already there? If you're considering this path or are already on it, you might wonder about the career prospects and advancement opportunities that lie ahead.

Once you’ve started, your path as a penetration tester can unfold in many directions.

In cyber security, every step forward opens new doors and challenges, keeping the pentester career path thrilling and rewarding.

Join us as we discuss the pentester career path and break down what positions you can enter and any expert positions that may be available if you want to take your career further.

Understanding the Role of a Penetration Tester

Before we dive into other areas, let's take a moment to discuss what a penetration tester is.

A penetration tester is responsible for conducting tests on networks and other assets with the primary goal of simulating a hacker's actions.

Penetration testers must adhere to a specific “scope” from the client, which outlines what they are allowed and not allowed to do during the testing process.

For example, a client may only want the tester to attempt to breach a certain server while avoiding any interaction with the domain controller.

The most important responsibility of a penetration tester is to provide the client with a report. This report outlines both the areas where the client is doing well in terms of security and those that require remediation.

Feeder Roles

Entering cyber security without any prior experience in IT is certainly possible, but certain feeder roles can help you get your foot in the door. These roles include IT support, systems administrator, and web developer, among others.

While these roles are not strictly necessary, they equip you with valuable skills, such as hands-on experience with operating systems, networking, analytical, and communication, to name a few, that can ease your transition into the role of a penetration tester.

General Cyber Security Roles

What are some general cyber security roles that can help you transition into a penetration tester role?

You could take a broader approach to becoming a penetration tester by taking on positions like a SOC analyst, cyber security analyst, or cyber security auditor.

These positions can give you skills and experiences that will be useful to you once you transition into the more specialized role of a pentester.

SOC Analyst: This role gives you exposure to real-time security monitoring and can teach you a lot about how attacks happen, which is useful for understanding what you'll be simulating as a pentester.

Security Analyst: In this role, you'll likely learn about risk assessments, security policies, and possibly even some basic vulnerability assessments, which are directly applicable to penetration testing.

Security Auditor: This role will give you a broad overview of security policies and configurations, teaching you what "good" security looks like — knowledge that's useful for identifying “bad” security later on.

The roles that will provide you with the most direct exposure to penetration testing tasks are those of junior penetration tester and vulnerability tester. If possible, you should aim for one of these positions as an initial step toward transitioning into a full-fledged penetration tester role. See our article A Newbie’s Guide to Finding a Cyber Security Job for steps and advice.

Jr. Penetration Tester: As a junior penetration tester, you'll be doing the job you ultimately want but at a less advanced level, including doing initial reconnaissance, running scans, or testing less critical systems. This is perhaps the most direct path to becoming a full-fledged pentester, and you will most likely be mentored by experienced penetration testers.

Vulnerability Tester: This role is often very similar to a penetration tester but might focus more on using automated tools to find security vulnerabilities rather than manually exploiting them. This role will give you an excellent foundation in vulnerability identification.

Cyber Security Career Pathway

Penetration Tester Positions

10 Penetration Tester Positions

Before we discuss the different penetration tester positions, let's first talk about some of the key responsibilities of a penetration tester.

Regardless of the type of penetration test being performed, you must follow a penetration testing methodology. These eight steps are crucial to performing a successful test.

Penetration Testing Steps

For a detailed look at these steps, please see our article, Penetration Testing Steps: A Comprehensive Assessment Guide.

Some of the key responsibilities of a penetration tester include conducting assessments, identifying vulnerabilities within systems, and writing detailed reports. It’s also important to stay updated with current trends. Other responsibilities include utilizing a range of tools and ensuring you are continuously learning and improving your skills.  

You have two options when it comes to being a penetration tester. You can stay general and continue on as a network pentester, where you assess and fortify the security of network systems, or you can add specialized areas to your expertise, such as web app or wireless pentesting.

Following the path of specialization, here are ten unique penetration testing roles that you might consider branching off into. These positions will likely require you to take training specific to these areas and any certifications that can prove to current or future employers that you have the skills for these specialized roles.

Web Application Pentester

Web application pentesters specialize in finding vulnerabilities in web applications. This includes testing website architecture, user authentication, and data protection mechanisms.

Scope

Engage in tasks like testing user authentication, session management, input validation, and exploiting vulnerabilities such as SQL injection, Cross-Site Scripting (XSS), and Cross-Site Request Forgery (CSRF).

Tools

Use tools like Burp Suite for intercepting and modifying web traffic, OWASP ZAP for automated scanning, and SQLmap for database exploitation.

Skills Needed

  • Strong understanding of web languages like HTML and JavaScript and server-side languages like PHP, Python, or Ruby.
  • Good understanding of HTTP/HTTPS and understanding of cookies and sessions.
  • Familiarity with databases, encryption, authentication, and authorization mechanisms like OAuth and JWT.
  • Good grasp of the vulnerabilities listed in the OWASP top ten.

Recommended Courses

API Pentester

API pentesters specialize in assessing the security of Application Programming Interfaces (APIs), which are essential for data exchange between different software systems.

See how Blue Hat Hackers fortify security in our article What Is a Blue Hat Hacker? Defending Applications Pre-Launch.

Scope

Primarily assess areas like authentication, authorization, data exposure, and rate-limiting. They often focus on RESTful APIs but may also work on SOAP or GraphQL APIs.

Tools

Frequently use Burp Suite and OWASP Zap for its API scanning capabilities, Postman for manual testing, and specialized tools like SoapUI for SOAP APIs.

Skills Needed

  • Proficiency in RESTful and SOAP APIs, as well as data formats like JSON and XML.
  • Understanding of HTTP methods, status codes, and headers.
  • Knowledge of  API keys, OAuth tokens, and JWT.
  • Experience in using API testing tools and frameworks for both manual and automated testing.

Recommended Courses

Mobile Application Pentester

Mobile application pentesters focus on mobile apps, testing them for security vulnerabilities related to data storage, communication, and unauthorized access.

Scope

Primarily assess vulnerabilities related to insecure data storage, insecure communication, weak authentication, and unauthorized access to sensitive features within the app.

Tools

Use specialized tools like Drozer and MobS. The tool Frida is utilized for dynamic analysis, while Xcode or Android Studio is used for static code analysis.

Skills Needed

  • Understanding of mobile OS’ and app sandboxing mechanisms.
  • Familiarity with mobile programming languages like Java for Android and Swift for iOS.
  • Proficiency in reversing mobile app binaries and understanding mobile app obfuscation techniques.

Recommended Courses

Cloud Pentester

Cloud pentesters specialize in assessing the security of cloud services and architectures, including configuration issues, access controls, and data encryption.

Scope

Check for misconfigurations, insecure data storage, and access controls, as well as test identity and access management, storage protections, and network security, and evaluate logging, monitoring, and cloud service vulnerabilities.

Tools

Commonly use cloud-specific command-line tools like AWS CLI and Azure CLI and specialized penetration testing tools like MicroBurst, Scout Suite, PurplePanda, and CloudBrute.

Skills Needed

  • Deep understanding of various cloud service models and architectures such as IaaS and PaaS.
  • Proficiency in scripting languages like Python or Bash for automation.
  • Knowledge of cloud-native security features like IAM roles, security groups, and encryption options.

Recommended Courses

IoT Pentester

IoT pentesters focus on the Internet of Things devices like smart home systems and wearables.

Scope

Assess the security of device firmware, hardware interfaces, data communication protocols, and cloud or mobile app interactions.

Tools

Use tools like Firmware Analysis Toolkit (FAT) to identify vulnerabilities in firmware, JTAG debuggers for hardware interfaces, and Wireshark to analyze network traffic.

Skills Needed

  • Experience in hardware hacking and ability to perform soldering or use hardware debugging interfaces.
  • Understanding of IoT communication protocols like MQTT, CoAP, and Zigbee.
  • Familiarity with programming languages like Java, C, or Python.

Recommended Courses

Social Engineering Pentester

Social engineering pentesters specialize in testing the human element of security, using techniques like phishing and pretexting to test an organization’s awareness and response.

Scope

Employ techniques like phishing, vishing (voice phishing), pretexting, and baiting to evaluate an organization’s vulnerability to human-based attacks.

Tools

Use social engineering toolkits like  GoPhish or SET (Social-Engineer Toolkit) for phishing campaigns and software like SpoofCard for caller ID spoofing in vishing attacks. Other tools might include Maltego and WifiPhisher.

Skills Needed

  • Exceptional interpersonal and communication skills to successfully manipulate targets.
  • Creative problem-solving to adapt social engineering tactics on the fly.
  • An understanding of human psychology and behavior.

Recommended Courses

Physical Pentester

Physical pentesters evaluate the physical security in place at a facility, including access controls and surveillance systems.

Scope

Tasks may include lock picking, badge cloning, tailgating, and social engineering to gain physical access to a secured area. They also evaluate the internal security of sensitive areas, including server rooms, executive offices, and R&D labs.

Tools

Common tools used include lock pick sets, RFID cloners, hidden cameras, disguises, fake badges and IDs, and social engineering pretexting props. Once inside a location, Wi-Fi sniffers and network taps may be used. Under-door tools and electronic bypass devices can also help open locked doors.

Skills Needed

  • Proficiency in lock picking and understanding of various physical lock mechanisms.
  • Technical skills to identify gaps in camera coverage and badge reader weaknesses.
  • Strong understanding of surveillance technologies like CCTV and motion sensors.
  • Social engineering skills.

Recommended Courses

Wireless Pentester

Wireless pentesters focus on identifying vulnerabilities in wireless networks, including Wi-Fi, Bluetooth, and even radio-frequency identification (RFID) systems.

Scope

Check for vulnerabilities of poor encryption and weak authentication and attempt to install rogue access points or an Evil Twin.

Tools

Wireshark for packet capturing, Aircrack-ng for cracking Wi-Fi passwords, and Ubertooth for Bluetooth sniffing. Wifi Pineapple for conducting advanced wireless attacks and network reconnaissance by creating rogue access points and capturing traffic.

A Wi-Fi adapter is essential for a wireless pentester. See the Best WiFi Adapters for Kali Linux to Buy.

Skills Needed

  • Deep understanding of wireless protocols and encryption methods.
  • Familiarity with radio frequency (RF) technologies.
  • Proficiency in using wireless sniffing and injection tools.

Recommended Courses

Automotive Security Pentester

Automotive security pentesters are specialized pentesters focusing on the vulnerabilities in automotive systems, including car software and hardware.

Scope

Tasks may involve CAN bus sniffing, firmware analysis, and even physical tampering with vehicle controls.

Tools

CAN bus sniffers, diagnostic OBD-II tools, and JTAG debuggers for firmware analysis.

Skills Needed

  • Understanding of automotive technologies and communication protocols like CAN or LIN.
  • Familiarity with embedded systems and real-time operating systems (RTOS).
  • Hands-on experience with hardware debugging tools.

SCADA/ICS Pentester

SCADA/ICS pentesters focus on industrial control systems and SCADA (Supervisory Control and Data Acquisition) systems, which are critical in industries like manufacturing, energy, and utilities.

Scope

Evaluate the security of control systems, PLCs, and industrial networking protocols.

Tools

Modbus scanners, PLC programming tools, and industrial firewalls for network segmentation tests. Other tools like Metasploit, Shodan, and Wireshark.

Skills Needed

  • Deep understanding of industrial processes and control system architectures.
  • Familiarity with industrial networking protocols like Modbus, DNP3, or Profinet.
  • Knowledge of safety measures and procedures to avoid disrupting industrial operations.

Recommended Courses

Expert Penetration Tester Positions

What if you are interested in moving beyond the role of a penetration tester? What options can you explore, and where can you take your career? Advanced positions usually entail years of experience and advanced certifications such as CISSP or CISM. Here are three opportunities you might consider.

Pentester Team Lead

The pentester team lead is responsible for overseeing a team of penetration testers, ensuring that assessments are conducted effectively and efficiently. The team lead is responsible for planning, executing, and managing penetration testing projects.

Scope

Define the testing scope and ensure quality reporting. The team lead will coordinate with clients and stakeholders, oversee report generation, and develop remediation strategies.

Tools

Familiarity with a wide range of penetration testing tools like Burp Suite, Metasploit, and Wireshark to mentor team members. Project management software like Jira or ClickUp and communication tools for team collaboration, including Slack and Microsoft Teams.

Skills Needed

  • Strong leadership and project management skills.
  • Advanced knowledge in various domains of cyber security.
  • Ability to mentor and upskill team members.

Recommended Courses

Exploit Developer

Exploit Developers are security professionals who work on discovering vulnerabilities in software and writing exploits to target these vulnerabilities. Their work is essential for understanding how attackers can gain unauthorized access to systems and how to prevent such access.

Scope

Identify software vulnerabilities and develop exploits to demonstrate their impact. Collaborate with penetration testers to simulate real-world attacks and provide insights into hardening software against exploitation.

Tools

Debuggers like GDB or WinDbg, disassemblers like IDA Pro and Ghidra, and programming languages like Python or C. Fuzzing tools like AFL or Peach Fuzzer to discover vulnerabilities.

Skills Needed

  • Deep understanding of operating systems, particularly memory management and process execution.
  • Proficiency in programming languages like C, C++, or Assembly for exploit development.
  • Thoroughly understand vulnerability types like buffer overflows, use-after-free, and privilege escalation.

Recommended Courses

CISO (Chief Information Security Officer)

The CISO is a C-level executive responsible for an organization's information and data security.

Scope

Oversee, develop, and implement the organization's cyber security strategy and program.

Oversee compliance and risk management while engaging with board members and other executives.

Tools

Enterprise-level security information and event management systems and risk assessment frameworks. Governance, risk management, and compliance platforms and executive dashboards for cyber security metrics.

Skills Needed

  • Strong leadership and management skills.
  • Broad understanding of cyber security, risk management, and compliance.
  • Ability to communicate effectively with both technical teams and business stakeholders.

Recommended Courses

Conclusion

As you've seen, the penetration tester career path can be quite unique, and you can branch off into many specialized roles.

You could focus on physical penetration testing, where you assess the security of physical locations or specialize in wireless testing to identify vulnerabilities in wireless networks. There are numerous options.

As you gain experience, you can move into expert-level positions, including the role of a lead penetration tester or even a CISO, where you oversee an organization's entire cyber security plan.

Are you looking to jump-start your career as a penetration tester? Join our Accelerator program today and join a community of like-minded individuals where you can access a career roadmap, connect with mentors, enroll in courses, and more.

Frequently Asked Questions

Level Up in Cyber Security: Join Our Membership Today!

vip cta image
vip cta details
  • Richard Dezso

    Richard is a cyber security enthusiast, eJPT, and ICCA who loves discovering new topics and never stops learning. In his home lab, he's always working on sharpening his offensive cyber security skills. He shares helpful advice through easy-to-understand blog posts that offer practical support for everyone. Additionally, Richard is dedicated to raising awareness for mental health. You can find Richard on LinkedIn, or to see his other projects, visit his Linktree.

>