Man on a mission to become a pentester

For the past 10 years ive been doing systems administration for a mix of Operating Systems Windows, freebsd, solaris and linux, i also have experience coding in c and in python as of late ive been working on getting into a pentester role ive passed my ceh currently working on my chfi (the employer has paid for both) once this is complete im going to take the offensive security course and then sit for the oscp exam. How does one break into the pentesting field with no real experience on the pentesting side of the house. Im not trying to become a paper tiger that is why im picking which certs i take.

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veritas_libertas

Hi. Have you checked out EH-Net Online Mag - Free Online Magazine for the Security Professional : EH-Net Online Mag There are certainly some knowledgeable individuals on TE, but EH is devoted to that kind security career. You appear to have a good foundation for Pen Testing. You may also want to check out eLearnSecurity - Worldwide IT Security training provider which I'm told is a good stepping stone between CEH and OSCP.

Master Of Puppets

You have a great background. You won't have that much trouble getting a job as a pen tester. What will seal the deal at this point, IMO, is putting a security edge to your skills. You already have the needed abilities in networking, operating systems and coding, now is the time to learn about the vulnerabilities in them, exploits etc. In other words, starting to explore the security side of them. The self study method will be great. OSCP is a probably the best choice. I would even say that after getting the OSCP, CEH and another security cert or two, if you want to, you should land a pen tester job.