I worked in IT from 2012 to 2015, spending about two years on a help desk and one year as a systems administrator for a post-production company. I eventually left after my hours increased and weekend work was added without additional pay, and I moved into carpet fitting because it paid better at the time. For the past five years, I've been running my own SaaS business. That experience has given me substantial hands-on work with Linux, Python, Docker, EKS, CI/CD pipelines, Jenkins, Nginx, Terraform, APIs, Stripe, and maintaining a production service with high uptime. I'm now considering returning to full-time IT, ideally in a DevOps, cloud, or systems engineering role. I'm concerned that my earlier IT experience is dated and that employers may not understand how relevant my SaaS work is. What would be the most realistic way to position myself and close any knowledge gaps without starting completely over?
5 Answers
Don’t quit your current source of income while searching. The technology job market is competitive, and even experienced candidates can spend months applying without getting responses. Refresh your cloud and automation knowledge, tailor your resume to each role, and use interviews as practice. Local government and public-sector employers can also be worth checking because some openings are posted only on their own career sites. They may not pay the most, but they can offer better stability and work-life balance.
Your biggest challenge may be explaining the SaaS period, not proving that you have experience. Employers could see “ran a SaaS” as either impressive production engineering or as an unrelated business venture, depending on how you describe it. Quantify your responsibilities and results: infrastructure scale, deployment frequency, uptime, cost savings, automation, migrations, security improvements, and the tools you used. Make it obvious that you operated a live service rather than simply taking a few online courses. You may be competitive for development, platform, or cloud roles if the technical depth is genuine.
Be prepared for the possibility that your first role back won’t have the title or salary you want. A systems administrator or systems engineer position could be a practical bridge while you rebuild industry connections and gain experience with current enterprise environments. A niche specialization—such as Kubernetes, cloud infrastructure, CI/CD, observability, or a particular platform—may help you stand out more than presenting yourself as a general IT candidate.
Ignore the blanket “don’t return to IT” advice. The field has frustrating employers and difficult periods, but it also has many different kinds of work and plenty of good teams. Focus on communicating with humility: users and business stakeholders aren’t stupid because they don’t know technology, and strong technical people still need communication skills. Your combination of earlier infrastructure experience and recent SaaS ownership could be valuable if you frame it around solving business problems, not just listing tools.
DevOps is usually a fairly senior role because it combines systems administration, networking, cloud platforms, automation, software development practices, and production support. Older help-desk and sysadmin experience alone probably won’t be enough, but running a real SaaS could be highly relevant if you can clearly document what you built and operated. Put the work into a portfolio or public repository where possible, including architecture diagrams, infrastructure-as-code, deployment workflows, monitoring, incident handling, and security decisions. You may also want to target systems engineer, cloud engineer, platform engineer, or DevOps-adjacent roles rather than only applying to jobs titled “DevOps.”
The SaaS work involved thousands of containers on Docker and EKS, automated customer deployments through APIs and Terraform, CI/CD pipelines, Linux, Python, Nginx, and maintaining roughly 99.99% uptime. I’ll work on presenting those accomplishments more clearly instead of letting employers assume it was just a small side project.
Also be honest about what you haven’t touched recently. IT changes quickly, and even experienced people forget technologies they haven’t used in years. Showing that you know your gaps and can learn quickly is more convincing than claiming to know everything.