I worked at Geek Squad for about five years, but I've been out of work for a few years. Will that experience help me get an IT job above entry level, or should I expect to start at the help desk?
Does five years at Geek Squad help me get back into IT?
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It should help, but I wouldn't count on skipping entry level. Help desk and desktop support are reasonable places to look, especially after a few years away.
Your experience may give you something to talk about that a brand new applicant doesn't have. Apply to roles that fit your skills even if the title sounds junior.
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A lot depends on what you actually did there. Troubleshooting, documenting problems, explaining fixes, and dealing with frustrated customers all transfer. Put the specific work on your resume rather than relying on the job title to explain it.
If the role was mostly sales, that can still show customer service skills, but it won't demonstrate the same technical depth as hands-on support.
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For a sysadmin role, the gap between retail support and managing business systems can be pretty big. Employers may ask about operating systems, networking, remediation, and tools like Active Directory. Brush up on the areas you've actually used and be honest about what you haven't.
A more advanced support role could be worth applying for if your technical skills match the posting, but the five years alone won't establish that match.
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Don't dismiss the people side. Explaining technical issues clearly and keeping track of customer problems are useful in support, and they matter in admin work too. They just need to be paired with the technical skills the job calls for.
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midrange_maven:
We didn't work with Active Directory, so that's one area I'd need to learn.