Career Path Advice

RPGChai

Hey everyone,

Just wanted to pick the brains of those more experienced than myself to hopefully give me some insight on what I should focus on career-wise.

Here's where I am currently: I started my IT career working part-time at a hair salon, working on their 2 computers and 1 server. I did all of the hardware/software installs and all of the support. Pretty basic stuff. After about a year of that, I got a job opportunity as a Desktop Tech II at a large insurance company (as a contracter through an IT staffing company), basically doing all break/fix work, new deployments, some light project work, etc. I did that for 2.5 years, learning a little bit about all of the different IT departments in the company.

About 7 months ago, I made a huge move within the company (still as a contracter) to a Senior Network Tech position. In this new position I administer Workstation Security over 12,000+ workstations in the company (GPO management, vulnerability patch deployment, run vulnerability scans, work with DoD IAVM bulletins, etc).

Here's where I want to go: I would like to eventually end up working in Network Security as a PenTester. I have no delusions of thinking that this means I will be "h4xx0ring all the time". I know that there are lots of meetings and documentation between the technical work, but this is the type of work that interests me.


What I want to know: What kind of career moves should I make to reach my end goal? I know that to be an efficient PenTester, you need to know the systems you are attacking. As I move from job to job, I'd like to focus on taking positions that will give me access to learning more indepth the systems I will be working against once I reach my dream-job.

Now here is where I need help from those who have more experience than me: What types of jobs do you consider "must-have" on the road to becoming a penetration tester? For example, I have my CCNA (and will be getting my CCNA Security through school this year), but do I need to work a couple of years as a network/firewall technician? Should I look at jobs with Linux administration (I have a small amount of Linux knowledge from my home lab)? Or should I take a more logical move (from where I am) and take a job more focused on Information Assurance?

Hopefully this makes sense to you guys. I look forward to hearing your responses!