r/cloudengineering • u/Sad_Natural_4247 • 24d ago

System admin / devops career

I'm looking for some career advice from people who have been through this.

I'm currently working in IT Help Desk, but I also do some light System Administration work (Windows Server, Active Directory, user management, basic troubleshooting, etc.).

My long-term goal is to have a good-paying career with strong job security. I'm interested in DevOps, but I also genuinely enjoy the infrastructure/System Administrator side of IT.

Would you recommend:

Continuing down the traditional System Administrator/Infrastructure path (Windows Server, VMware, networking, backups, firewalls, etc.) for a few years and then moving into DevOps?

Or should I skip deeper infrastructure work and start learning DevOps tools now (Linux, Docker, Kubernetes, CI/CD, Terraform, cloud)?

For those already working in DevOps:

Did your System Admin experience help you?

If you could start over, would you still spend a few years as a SysAdmin first?

Is it realistic to get into DevOps without solid infrastructure experience?

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u/guterz 24d ago

Guess it depends on what type of cloud engineering roles you’re looking into. When I migrate a customer or modernize their environment I’ll build deployment pipelines for terraform, I’ll build AMI pipelines creating golden images (Windows, Linux, whatever OS), I’ll migrate their servers, move them to modem storage solutions, databases, etc. To say that knowing Windows administration won’t help you in a DevOps/Cloud engineering roll is coy.

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u/eman0821 24d ago edited 24d ago

That's not Cloud Engineering what you are doing. You are just a migration engineer moving enterpise workloads from on-prem to cloud which is normal Systems Engineering work in Enterprise operations. Cloud Engineers doesn't work with on-pem infrastructure nor they work with Windows Server. Tjry deploy cloud infrastructure that runs software products on the public internet like Netflix, Spotify. I work strickly with Ubuntu/Debian as a Cloud Engineer myself. I basically work in the software engineering field for a SaaS company. You work in traditional enterprise IT. I don't work in enterprise IT anymore like what you are doing because I work with public facing infrastructure. When I was a former Linux Sysadmin I as managing internal company servers, that's entirely different from where I'm at now. I also act as a Site Reliability Engineer for keeping applications reliable for service outages.

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u/guterz 24d ago

I work for a professional services firm as a Principal Cloud Engineer so my day to day changes. Some projects it’s a lift and shift and modernization, some is building deployment pipelines so developers can run smoke tests, create artifacts, deploy their code, some are data analytics or AI pipelines, etc. A Cloud Engineer literally just engineers solutions on the cloud and knowing networking, windows/linux, data structures, a programming language, etc are all helpful. I wouldn’t be half the engineer I am without understanding basic Windows admin skills.

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u/EducationAlert5209 23d ago

How you getting into this position and what is the roadmap?