A comprehensive guide to pursuing a career in offensive security, including penetration testing and red teaming roles, skills needed, and career paths.
Author: Swetha Kannan
A Penetration Tester is a security professional hired by a company to assess their information security defenses and find vulnerabilities. Pentesters may also try to gain access to systems through social engineering measures like phishing, impersonation, or elicitation. Basically, a penetration tester is a hacker hired by a company to help defend against other hackers.
It's a lucrative, challenging line of work that's currently in high demand. Organizations across all industries need skilled professionals who can think like attackers to help them identify and fix security weaknesses before malicious actors can exploit them.
Understanding Offensive Security Roles
Before diving into the career path, it's important to understand the different roles within offensive security:
Penetration Tester
Penetration testing is the evaluation of computer systems through authorized simulated attacks. The purpose is to expose as many vulnerabilities as possible across the tested systems, so they can be addressed before exploitation during an actual cyber attack. Pentesters typically focus on:
- Network penetration testing
- Web application security testing
- Mobile application testing
- Social engineering assessments
- Physical security testing
Red Team Operator
Red teaming goes beyond traditional penetration testing. A red team simulates real-world cyberattacks to test an organization's overall security posture, including people, processes, and technology. Red team operators:
- Operate covertly, trying to remain undetected
- Test detection and response capabilities
- Use advanced persistent threat (APT) tactics
- Conduct social engineering at scale
- Evaluate security awareness and incident response
Key Differences
While both roles involve simulating attacks, penetration testing is typically a focused, time-boxed assessment of specific systems, often for compliance purposes. Red teaming is a more comprehensive, adversary-simulation exercise that tests the entire security program.
Steps to Becoming a Penetration Tester
Step 1: Build Strong Foundational Knowledge
As a beginner, you must be familiar with the fundamentals that underpin all security work:
- Networking: TCP/IP, DNS, HTTP/HTTPS, routing, firewalls, VPNs
- Operating Systems: Windows and Linux administration, command line proficiency
- Programming: Python, Bash scripting, understanding of web languages (JavaScript, SQL)
- Web Technologies: How web applications work, common architectures, APIs
- Security Fundamentals: CIA triad, common vulnerabilities, defense mechanisms
It takes years to build the necessary experience and knowledge to become a penetration tester. Like most security jobs, penetration testers often reach their position after years of experience in other technical roles like network engineer, system administrator, or software engineer.
Step 2: Learn the Tools of the Trade: Kali Linux
The journey to becoming a penetration tester inevitably runs through Kali Linux. Kali Linux is a free Linux distribution designed for and by penetration testers. It comes pre-installed with hundreds of security tools and is constantly updated by the Offensive Security community.
Essential tools to master include:
- Nmap: Network scanning and discovery
- Burp Suite: Web application security testing
- SQLmap: Automated SQL injection detection and exploitation
- Metasploit: Exploitation framework
- Wireshark: Network protocol analysis
- Hashcat/John the Ripper: Password cracking
- Gobuster/Dirbuster: Directory and file enumeration
- Nikto: Web server vulnerability scanning
Alternatively, you can use Parrot OS, which also has a vast array of security tools and is equally suitable for penetration testing.
Step 3: Get Hands-On Experience
Hands-on experience is absolutely essential. You will learn far more by doing than by simply listening to videos or reading books. Here's how to get practical experience:
Lab Environments
- TryHackMe: Guided, beginner-friendly rooms covering various security topics
- Hack The Box: More challenging machines for intermediate to advanced practice
- VulnHub: Downloadable vulnerable virtual machines
- PortSwigger Web Security Academy: Free web application security training
Home Lab
Set up your own lab environment to practice safely:
- Virtual machines with vulnerable configurations
- Practice network segmentation and pivoting
- Build and break your own applications
- Document everything you learn
Capture the Flag (CTF) Competitions
CTF competitions are excellent for developing skills in a competitive, time-limited environment. They cover various security domains and help develop problem-solving abilities under pressure.
Bug Bounty Programs
Platforms like HackerOne, Bugcrowd, and Synack allow you to legally test real-world applications and potentially earn rewards for finding vulnerabilities.
Step 4: Earn Relevant Certifications
Certifications validate your knowledge and demonstrate commitment to the field. Consider this progression:
Entry-Level Certifications
- CompTIA Network+: Foundational networking knowledge
- CompTIA Security+: Broad security fundamentals
- CompTIA Linux+: Linux administration skills
Intermediate Certifications
- CompTIA PenTest+: Penetration testing methodology
- Certified Ethical Hacker (CEH): Theoretical hacking knowledge
- eLearnSecurity Junior Penetration Tester (eJPT): Practical, hands-on certification
Advanced Certifications
- Offensive Security Certified Professional (OSCP): The gold standard for penetration testers—a challenging, hands-on 24-hour exam
- Certified Red Team Professional (CRTO): Red team operations and Cobalt Strike
- GIAC Penetration Tester (GPEN): Comprehensive penetration testing
- Offensive Security Web Expert (OSWE): Advanced web application attacks
The OSCP is particularly valued because it proves practical hacking skills rather than just theoretical knowledge. Many employers specifically seek candidates with this certification.
Step 5: Getting Your Foot in the Door
Breaking into offensive security can be challenging. Here are strategies to land your first role:
Networking
- Attend security conferences (DEF CON, BSides events, local meetups)
- Engage with the security community on Twitter/X and Discord
- Build relationships with professionals already in the field
- Seek out mentors who can guide your career development
Community Involvement
- Join non-profits that support beginners and underrepresented groups in cybersecurity
- Contribute to open-source security tools
- Write blog posts about your learning journey
- Share your CTF write-ups and walkthroughs
Alternative Entry Points
Consider starting in related roles that provide relevant experience:
- Security Operations Center (SOC) analyst
- Vulnerability management analyst
- Security engineer
- IT audit or GRC roles
Penetration Tester Roles and Responsibilities
As a penetration tester, your core responsibilities include:
- Reconnaissance: Gathering information about target systems and organizations
- Vulnerability identification: Finding security weaknesses in systems, networks, and applications
- Exploitation: Demonstrating how vulnerabilities can be leveraged by attackers
- Post-exploitation: Determining what an attacker could achieve after initial access
- Documentation: Writing clear, actionable reports that help organizations remediate issues
- Consulting: Advising clients on security improvements and best practices
Career Outlook and Advancement
Offensive security is a rapidly growing field as cyberattacks become more frequent and severe. The career path offers:
- Strong compensation and job security
- Continuous learning and new challenges
- Opportunities to advance into senior technical or management roles
- Potential for consulting, bug bounty hunting, or entrepreneurship
Career progression typically follows:
- Junior Penetration Tester
- Penetration Tester
- Senior Penetration Tester
- Lead/Principal Penetration Tester
- Red Team Lead/Manager
- Director of Offensive Security
- CISO or Security Executive
Conclusion
A career in offensive security offers exciting opportunities to apply creative problem-solving skills to real-world security challenges. While the path requires significant dedication and continuous learning, the rewards—both professional and financial—are substantial. Start building your foundational skills today, get hands-on experience, earn relevant certifications, and engage with the security community. With persistence and passion, you can build a successful career helping organizations defend against cyber threats.
About the Author: Swetha Kannan has over 6 years of experience in cyber security consulting, working across several industrial sectors. She currently volunteers with Cybertrust America as a Tech Lead and Director. She compiled this article with significant research from various Security Training forums and websites.
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