No milestone triggered this post. No anniversary, no big launch. Just five years behind me and enough distance to see the shape of them clearly.
Here is what I learned, and where it came from.
Tide: Building IT From Zero
I joined Tide as employee 39. There was no exactly IT department to speak of.
That meant setting up the systems, the access controls(physical and digital), the device management, the processes that let a growing company actually function without breaking. I scaled that IT function across three offices: Sofia(Bulgaria), London(United Kingdom), and Hyderabad(India).
Building from scratch teaches you things a mature IT department never will.
You learn what actually matters versus what looks good on a slide.
You learn to make decisions with incomplete information because there is no legacy system to defer to.
You learn that IT exists to serve the business, not the other way around.
That lesson stuck with me for everything that came after.
SpotMe: Running IT Across Distance
At SpotMe, an event-tech company of 100+ people, I ran distributed IT operations. Different challenge, same core problem: how do you keep a company’s technology coherent when the people using it are scattered across time zones, offices, and working styles.
This is where I got sharper at the operational side. Identity management, endpoint management, SaaS administration, all at a scale where manual fixes stop working and you need real systems and real processes.
It also taught me something less technical: how to be the calm, reliable point of contact when things are uncertain. Distributed teams need that more than they need any specific tool.
Freelancing: Where It All Came Together
Employment teaches you how to run IT inside one company’s walls. Freelancing teaches you something different: how IT needs actually shift depending on the business, the sector, the size, the ambitions.
Since going independent, I have worked with multiple organizations, each with a different relationship to technology. Some needed structure. Some needed security discipline. Some just needed someone who could translate between what the business wanted and what the systems could actually do.
Freelancing forced me to get good at things employment never demanded: sales, positioning, scoping, pricing, explaining technical value to people who do not think in technical terms. It also gave me the freedom to build my own tools, including a structured IT assessment framework, rather than just operating inside someone else’s.
The biggest shift was mindset. In-house, IT often gets treated as a cost center or a support function. Freelancing forces you to prove value constantly, which forces you to actually deliver it. That pressure made me better at aligning IT decisions with what the business is actually trying to achieve, not just what best practice says on paper.
The Thread Running Through All of It
Three different environments. One consistent lesson: IT that is not aligned with business needs is just infrastructure for its own sake. It does not matter how clean the architecture is if it is not solving a real problem for real people trying to run a real business.
Five years in, that is the principle I keep coming back to. Not the tools, not the platforms, not the certifications. Just that one question, asked over and over: does this actually serve the business, or does it just look like it does.
No milestone. Just five years of learning that lesson from three different angles.