#7 Think Outside the Box to Land First Pentesting Job ft. Ryan Daub

The Hacker's Cache

In this conversation, Kyser Clark interviews Ryan Daub, an Offensive Security Analyst Associate, about his journey in cybersecurity and his current role as an internal penetration tester for healthcare organizations. They discuss topics such as landing a job in cybersecurity, the role of AI in penetration testing, the differences between internal and consulting pentesting, the importance of collaboration between red and blue teams, and the value of continuous learning in the field. Ryan also shares his advice for aspiring cybersecurity professionals.
Connect with Ryan Daub on LinkedIn: https://www.linkedin.com/in/ryan-daub-b87b9b216/
Takeaways

• Landing a job in cybersecurity requires dedication, self-awareness, and demonstrating your skills through personal projects and documentation.
• AI is a useful tool in penetration testing, but it is not yet capable of fully automating the process due to the complexity and constant evolution of technology and environments.
• The role of an internal penetration tester in healthcare organizations involves conducting compliance testing, red team engagements, and collaborating closely with the blue team.
• Continuous learning and staying up to date with industry trends and certifications, such as OSCP and CRTO, are essential for career growth in offensive security.
• Collaboration and knowledge sharing within the cybersecurity community are crucial for personal and professional development.

Connect
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Music by Karl Casey @ White Bat Audio
Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information.
Opinions are my own and may not represent the positions of my employer.

Chapters

1. Introduction and Backgrounds (00:00:00)

2. Landing a Role in Cybersecurity (00:05:50)

3. Rapid Fire Questions and AI in Pentesting (00:09:45)

4. Internal vs. Consulting Pentesting (00:15:27)

5. Working with Blue Teams and External Pentesters (00:20:29)

6. Current Training, Future Goals, and Final Advice (00:24:45)