From Pentester to Red Teamer: Navigating the Skills Needed for the Transition

If you're already in the cybersecurity field or looking to break in, you've probably noticed that the industry is constantly shifting. It's an endless game of cat and mouse between defenders and attackers. Many cybersecurity professionals start their journey as penetration testers (pentester), tasked with identifying vulnerabilities in networks, systems, or applications. But for those looking to move from finding holes in security to simulating real adversarial attacks, the jump to red teaming is a big one.

It's not just a “level up”, it's a mindset shift, a deeper technical dive, and a move into a role that looks at security from every angle.

Pentester vs. Red Teamer: What's the Difference?

As a Pentester, your main focus is on identifying vulnerabilities in a controlled, often isolated, environment. You typically work through a structured process, using a well defined methodology like OWASP for web applications or other vulnerability frameworks. The aim is to highlight weaknesses and deliver specific recommendations to improve security. This means pentesters are very methodical, targeting specific systems or applications for a focused assessment.

In contrast, a Red Teamer operates more like a real-world adversary. Instead of finding vulnerabilities, you're simulating actual attack scenarios to understand how far an attacker could get and how well an organisation can detect and respond. It's not just technical systems you're assessing, but there full defensive posture, including people, processes, and detection capabilities. Red teaming requires pentesting skills but adds in a whole other layer, you're emulating threats, using adversary tactics, and focusing on stealth to see if you can fly under the radar.

How a Pentester's Skillset Evolves for Red Teaming

May red teamers start with a strong penetration testing background, so the jump to red teaming builds on those foundational skills. Here's how key skills evolve from pentesting to red teaming:

1. Exploitation Techniques: Basic to Advanced

Pentester: As a pentester, you're comfortable with common exploitation techniques, usually leveraging tools like Metasploit or Burp Suite to uncover and exploit web or network vulnerabilities.

Red Teamer: In red teaming, the game changes. You're moving into more advanced exploitation, covering a wider range of systems and techniques. Tools like Cobalt Strike are essential, and you'll be simulating sophisticated attacks, including advanced payloads and lateral movement tactics to mimic high-level threats.

2. Command and Control (C2) Frameworks: Building Persistence

Pentester: In pentesting, persistence isn't always a priority. You find a vulnerability, exploit it, and report the results.

Red Teamer: Persistence is critical. You're establishing and maintaining C2 communications while evading detection, much like real-world attackers. Familiarity with frameworks like Mythic and Posh C2 enables you to test defenses and remain hidden, mimicking the stealth and persistence of sophisticated threat actors.

3. Adversary Emulation: Beyond Finding Vulnerabilities

Pentester: Your focus is on vulnerabilities - identifying and exploiting them in a technical, structured approach.

Red Teamer: Red teaming means stepping into an attacker's shoes. You're no longer just finding vulnerabilities, you're emulating the behavior of threat actors. Frameworks like MITRE ATT&CK become essential, letting you build scenarios that test the full extent of an organisation’s detection and response.

4. Social Engineering Techniques: Expanding the Attack Surface

Pentester: Pentesting is usually limited to technical testing and doesn't often include social engineering, though phishing simulations might sometimes be included.

Red Teamer: Red teaming takes on social engineering in full force. Phishing, pretexting, or even physical intrusion are tactics you'll employ, testing an organisation's human defenses along with its technical controls.

5. Reporting and Communication Skills: Tailoring the Message

Pentester: As a pentester, your reports focus on technical findings and remediation steps for each identified vulnerability. Clear communication is important but typically stays within technical teams.

Red Teamer: For a red teamer, reporting is more strategic and narrative-based. You're documenting attack paths, impact, and the organisation's response gaps. This means translating technical jargon into clear risks and actions for both technical and executive audiences, offering insights that help teams strengthen security holistically.

Soft Skills and Mindset: The Core of Red Teaming

For both roles, technical expertise is vital, but moving into red teaming means enhancing your soft skills too. Communication, collaboration, and a proactive, strategic mindset are key. Red teamers work closely with different stakeholders, often mentoring junior staff and contribute to broader security awareness. These skills are what help bridge the gap between finding vulnerabilities and building an organisation wide defensive posture.

From Pentester to Red Teamer: Embracing the Challenge

Transitioning from pentesting to red teaming is an exciting and challenging move that broadens your view of cyber security. By building on the technical skills of a pentester and developing a strategic, adversary-focused mindset, you're positioning yourself to make a real impact in an organisation's security. Red teaming isn't just a job, it's a commitment to pushing defenses to their limit and ensuring resilience against real world threats.

If you're ready to take on this challenge, embrace the complexity and step confidently into a role where you'll learn, adapt, and continuously test your mettle. The journey from pentester to red teamer is one of growth, resilience, and an ever-deepening understanding of security.

So dive in and start exploring, you're in for a rewarding, dynamic career that's anything but ordinary.