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What are recommendations to make the transition from a systems administrator into cybersecurity?


Kenneth Boyd Belleville, IL

I am looking to transition into the cybersecurity realm. I recently acquired my CompTIA Advanced Security Practitioner (CASP+) certification and have been working as a systems administrator for approximately 3 years. What are some recommendations of tools, tips, and technology to assist with the transition? I also plan to earn my CISSP later this year.

22 April 2022 7 replies Career Advancement



Gary Rossi Napa, CA

Kenneth - you can also use LinkedIn to network with individuals that have done the same thing - search cyber security companies and then the people send them a tailored connection request to set up an informational interview - secondly connect with me to broaden your network -


Justin Baker Evans, GA


A lot of great information and advice, especially from Adam. I'll add the following from my experience: network, apply, network, interview, network, wash-rinse-repeat. I'd recommend some level of caution as this *could* lead to burnout (as it did with me, initially).

I broke into infosec in 2018 with zero years of IT/cyber experience, though intel/SIGINT experience certainly helped. However, the biggest plus I had going for me was completing the SANS VetSuccess program. I recommend looking into that to see if you're a candidate. Regardless of whether you are, I would definitely recommend joining the VetSec community. You can find tons of guidance just by searching through the Slack, let alone by directly engaging. There's also a workflow for requesting a mentor.

Best of luck, Kenneth! It's only a matter of time until you've knocked this goal out.


Adam Couch Ladera Ranch, CA

Hi Kenneth,

I recommend applying for analyst or engineering jobs right away and getting as many 'at bats' in interviewing as you can because you're going to see a large variance in what you're asked to do in the role, cultures, org structures, etc. You have to start somewhere and landing a job will get you the experience you need to make moves, and I think this is a two move approach. And by that I mean you're likely going to land a job to get you started, and the next job will likely be the one you're looking for.

Simultaneously sharpen or grown your cybersecurity specific skills by leveraging free training to build on your sysadmin experience. With that experience I'd look at vulnerability management as a possible point of entry. A SOC analyst position would likely leverage your skills too and aid in a segue to a position in incident or vulnerability management.

Be flexible with locations and don't be afraid to admit you don't know something but will find the answer - then go find it and communicate back to whomever asked. You're a former military member so you're trainable and understand 24x7 operations, just ask most larger security teams operate. And has good data to look at trends on jobs and other insights to how to land your next cybersecurity job.

Go get it, and good luck.



Mark Young Salem, NH

Please contact me if you want to work for Raytheon Technologies, if you have a clearance and cert your a good candidate. ISSO or ISSM



Gabriel Hoffman Dayton, OH

Kenneth, I can connect you to a cybersecurity expert from the company I just retired from (Northrop Grumman), if you wish.


Jerry Welsh Middleville, MI

Start Informational Interviewing with employees doing what you want to move into. Research job postings on job boards. To know what you have to do you need to know the career. Also hook up with groups on LI and fFacebook professional. People like to help service members and veterans with information, stay away from asking for work! Seek information and build a network. Thanks for your service.


ACP AdvisorNet Staff New York, NY

Hi Kenneth,

Thank you for your service and your question! It sounds like you’re already on your way to success with those certificates.

To learn more from industry professionals I would recommend utilizing the "Community" tab on the ACP AdvisorNet website. You can refine your search to locate an Advisor or a fellow Veteran based on your specific career or company preferences (such as Information Technology and Security or any Cyber-based company). You’ll be able to connect with experts within the field to see what they recommend as far as tools, tips, and technologies moving forward.


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