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IT Support to DevOps: The Only Roadmap That Actually Works

LeonIT Team

Stop resetting passwords. Start building infrastructure. Here is the step-by-step guide to doubling your salary by moving from Helpdesk to DevOps.

You are tired. You just spent 30 minutes explaining to "Karen in Accounting" that her monitor isn't broken, it's just unplugged. You make $55,000 a year. Meanwhile, the DevOps Engineer down the hall makes $140,000. He wears a hoodie. He doesn't talk to users. He leaves at 4 PM.

You want his life. The good news? You can have it. The bad news? You have to stop clicking buttons and start writing code.

For more on career pivots, check out our guide on high paying tech jobs.

The Scenario

You are an IT Support Specialist. You are good at troubleshooting. You know Windows. You know Active Directory. But you are stuck. You apply for "System Administrator" jobs, but they all ask for "Cloud Experience" and "Terraform." You are in the "GUI Trap." You can fix anything if it has a menu, but you are lost in a black terminal window.

The Old Way vs. The New Way

The old way was "SysAdmin." The new way is "DevOps."

Feature The Old Way (IT Support) The New Way (DevOps)
Tool Mouse (GUI). Keyboard (Terminal).
Task "Reset Password." "Automate Password Rotation."
Scale Manage 1 server. Manage 1,000 servers.
Mindset "Fix it when it breaks." "Code it so it never breaks."
Salary $50k - $70k. $110k - $180k.

1. Kill the Mouse (Learn Linux)

You cannot be a DevOps engineer on Windows. 90% of the cloud runs on Linux. The Challenge: For the next week, do not touch your mouse. Try to navigate your file system using only the Command Line (CLI). Learn these commands: ls, cd, grep, chmod, chown, ssh. If you can't SSH into a server and restart a service without a GUI, you are not ready.

2. Learn One Cloud (And Ignore the Rest)

Recruiters don't care if you know "a little bit of everything." They want an expert. Pick AWS. It has the biggest market share. Do not get the "Cloud Practitioner" cert. It's useless fluff. Get the AWS Solutions Architect Associate. It forces you to understand networking (VPCs, Subnets) which is the hardest part for IT Support people.

3. Infrastructure as Code (Terraform)

This is the magic key. In IT Support, if you need a server, you click "New Virtual Machine." In DevOps, you write a text file that says resource "aws_instance" "web". You run terraform apply, and the server appears. Why this matters: You can create 100 servers as fast as 1. That is why DevOps pays more. Scale.

4. Learn Python (Not PowerShell)

PowerShell is great for Windows. Python is great for everything. You don't need to be a software developer. You just need to write "Glue Code."

  • Script A takes data from AWS.
  • Script B puts it into a database.
  • Python connects A and B.

5. The "Portfolio" Project

You can't get a job without experience. You can't get experience without a job. The Loophole: Build a project.

  1. Write a Python script that says "Hello World."
  2. Wrap it in a Docker container.
  3. Use Terraform to launch an AWS server.
  4. Deploy the container to the server using GitHub Actions. Put this on your GitHub. Put the link on your resume. You are now a DevOps Engineer.

The Real Numbers

The salary jump is violent.

Role Average Salary Stress Source
Helpdesk L1 $45,000 Angry Users.
SysAdmin $75,000 On-Call Nightmares.
Junior DevOps $105,000 Breaking Production.
Senior DevOps $160,000 Architecture Debates.

Frequently Asked Questions

Q: Do I need a degree? A: No. I have worked with DevOps leads who were music majors. Certs + GitHub Portfolio > Degree.

Q: Is it too late to start? A: No. The cloud is still growing. But the "easy" entry-level jobs are gone. You have to be good.

Q: What about AI? A: AI writes great code. AI is terrible at debugging complex infrastructure. DevOps is 90% debugging. You are safe (for now).

Q: Can I skip Linux? A: No. Even on Azure (Microsoft's cloud), the servers are mostly Linux. Swallow the pill. Learn bash.

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LeonIT Team

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Our team of IT professionals brings years of experience in software development, AI automation, and digital transformation solutions.

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