How to Become a Penetration Tester

Why Become a Penetration Tester?

Penetration testing is one of the most exciting and rewarding careers in cybersecurity. You get paid to think like a hacker, break into systems legally, and help organizations strengthen their defenses before real attackers find weaknesses.

What makes this role compelling:

• High demand: Every organization needs security testing
• Continuous learning: New vulnerabilities and techniques keep the work fresh
• Impactful work: Directly prevent data breaches and security incidents
• Intellectual challenge: Every engagement is a unique puzzle to solve
• Strong compensation: Pentesting is among the highest-paid cybersecurity roles

What Does a Penetration Tester Actually Do?

As a Penetration Tester, you simulate real-world attacks to find vulnerabilities before malicious actors do. A typical engagement includes:

• Reconnaissance: Gathering information about the target through OSINT, DNS enumeration, and network scanning
• Vulnerability Discovery: Identifying weaknesses in networks, applications, and systems
• Exploitation: Safely exploiting vulnerabilities to demonstrate real-world impact
• Post-Exploitation: Simulating lateral movement, privilege escalation, and data exfiltration
• Reporting: Documenting findings with clear remediation recommendations

Types of Penetration Testing

Different engagements focus on different areas:

Skills That Set You Apart

Technical Mastery

1. Linux Proficiency: Kali Linux is your primary operating system. Master the command line, file system, and common security tools.

2. Networking Deep Dive: Understand TCP/IP at a packet level. Know how to analyze network traffic, pivot between subnets, and identify misconfigurations.

3. Web Application Security: The majority of penetration testing involves web apps. Master OWASP Top 10 vulnerabilities, authentication bypasses, and injection attacks.

4. Active Directory: Most enterprises run on AD. Understanding Kerberos, delegation attacks, and AD misconfigurations is crucial for internal assessments.

5. Scripting and Automation: Python, Bash, and PowerShell let you write custom exploits, automate reconnaissance, and extend existing tools.

The Hacker Mindset

Beyond technical skills, successful pentesters share key traits:

• Curiosity: Always asking "what if?" and exploring unexpected paths
• Persistence: Spending hours on a single vulnerability without giving up
• Creativity: Finding unconventional attack chains that automated tools miss
• Methodical approach: Following systematic methodology while remaining adaptable

The Certification Path

Entry Level: Building Your Foundation

eJPT (eLearnSecurity Junior Penetration Tester)

• Practical, hands-on exam
• Great first certification
• Builds confidence in methodology

CompTIA PenTest+

• Vendor-neutral
• Covers methodology and compliance
• Good for DoD environments

PNPT (Practical Network Penetration Tester)

• Affordable ($399)
• Real-world AD lab environment
• 5-day practical exam

Intermediate: The Industry Standard

OSCP (Offensive Security Certified Professional)

• The gold standard for pentesters
• 24-hour hands-on exam
• Proves real-world hacking ability
• Often required for senior roles

Advanced: Specialization

Choose based on your focus area:

• OSWE: Web application security
• CRTO: Red team operations with C2 frameworks
• OSEP: Advanced evasion techniques
• GPEN/GWAPT: GIAC certifications for formal environments

Building Your Portfolio

Since penetration testing is skills-based, demonstrating ability is crucial:

CTF Competitions

• Compete on platforms like CTFtime
• Document your solves and methodologies
• Team competitions show collaboration skills

Bug Bounty Hunting

• Real-world experience finding vulnerabilities
• Public recognition on HackerOne/Bugcrowd
• Actual findings prove capability

Home Lab

• Build vulnerable networks to practice on
• Document attack chains and techniques
• Create realistic AD environments

Technical Writing

• Write blog posts explaining vulnerabilities
• Create CTF writeups
• Share tool development projects on GitHub

The Job Search

Entry Points

Junior Penetration Tester

• Support senior testers
• Focus on specific assessment types
• Learn methodology and reporting

Vulnerability Analyst

• Run vulnerability scans
• Triage and validate findings
• Bridge to hands-on testing

SOC Analyst with Offensive Interest

• Build defensive experience first
• Transfer to pentesting later
• Understand what defenders see

Where to Find Jobs

• LinkedIn (filter for "penetration tester," "security consultant")
• InfoSec Jobs, CyberSecJobs
• Company career pages (NCC Group, Bishop Fox, CrowdStrike)
• Security conferences (job boards, networking)
• Consulting firms often hire at scale

Interview Preparation

Expect a mix of technical and practical assessments:

Technical Questions:

• "Walk me through how you would approach a network penetration test"
• "Explain Kerberoasting and how you would detect/prevent it"
• "What's the difference between stored and reflected XSS?"
• "How would you bypass antivirus detection?"

Practical Exercises:

• Capture the flag challenges
• Take-home vulnerable machine exercises
• Live hacking demonstrations

Common Challenges

Imposter Syndrome

The problem: Feeling like you don't know enough compared to senior testers. The solution: Everyone starts somewhere. Focus on fundamentals, document your learning, and embrace the continuous learning nature of security.

Information Overload

The problem: Too many tools, techniques, and attack paths to learn. The solution: Master one domain before expanding. Start with network or web app testing, get comfortable, then branch out.

Ethical Boundaries

The problem: Understanding what's legal and ethical. The solution: Always get written authorization. When in doubt, ask. Build strong professional ethics from day one.

Career Progression

Penetration testing offers multiple growth paths:

Technical Track

• Junior Pentester → Senior Pentester → Lead Pentester → Principal Consultant

Specialization

• Red Team Lead: Focus on adversary simulation
• Exploit Developer: Create custom exploits and tools
• Application Security Specialist: Deep web app expertise

Management

• Security Consulting Manager: Lead pentesting teams
• Offensive Security Director: Strategy and team building

Independent

• Bug Bounty Hunter: Full-time bounty hunting
• Independent Consultant: Run your own practice

Getting Started Today

If you're committed to becoming a Penetration Tester:

1. Start with fundamentals: Ensure solid networking and Linux skills
2. Create a TryHackMe account: Begin with beginner-friendly rooms
3. Set up a home lab: Practice in a safe environment
4. Pursue eJPT or PNPT: Get your first practical certification
5. Document everything: Blog your learning journey
6. Join the community: Discord servers, Twitter/X security community

The path is challenging but achievable. Organizations desperately need ethical hackers to find vulnerabilities before criminals do. Your future team is waiting.