Relaunching my career by building the tool I needed

There is a particular kind of quiet that comes with a career relaunch. The calendar empties out. The feedback loop you were used to, the one where work tells you every day whether you are doing well, goes silent. And you are left with a search that feels less like a plan and more like shouting into a well.

I know that quiet. On the last day of 2025 I left one of the largest cybersecurity software companies in the world, having owned reporting for the better part of a billion dollars in revenue, and woke up on January 1 with none of it. No title, no team, no dashboard to hide behind. Those first weeks felt less like a job search and more like re-learning who I was without a title in front of my name.

What I want to write about is not the hard part. It is what I did with it.

The search itself felt broken

The first thing I noticed, once I actually started applying, was how bad the tools were. Not the job boards. The part where you, one person, try to run a serious search across dozens of roles, keep track of who said what, remember to follow up, and learn anything at all from the whole exercise.

I have spent my career in revenue operations and analytics. Making messy, high-stakes processes legible is the actual job: take something people are running on instinct and memory, and give it stages, numbers, and a follow-up cadence so nothing important falls through. So it bothered me, more than it should have, that the most important process I had ever run for myself was the least organized.

I decided to build instead of just apply

At some point the frustration turned into a question I could not put down: what would it look like to run my job search the way I would run a real pipeline?

So I started building it. A way to score roles for fit so I spent my best effort where it counted. A way to track every application through real stages instead of a color-coded mess. A follow-up system that did not depend on me remembering. The tool I wished someone had handed me on day one.

I called it trajecktory.

I will be honest about why this helped, because it is not only the obvious reason. Yes, it made the search more organized. But the bigger thing was this: building it gave me back the feedback loop I had lost. On the days when no recruiter wrote back, when the search gave me nothing, the work still gave me something. A problem to solve. A thing that was a little better at the end of the day than it was at the start. That mattered more than I expected.

What building it taught me that applying alone would not have

A job search can make you feel like a candidate, a line in someone else's inbox, a yes or a no. Building something pushed back on that. It reminded me, daily, that I am a person who makes things, not just a person waiting to be chosen.

It also turned out to be the best interview material I have. When someone asks what I have been working on, I do not have to reach for a careful non-answer. I built a tool, I open-sourced it, I use it every day, and I can walk you through exactly why I made the choices I made. That is a very different conversation than explaining a gap. It is a demonstration instead of an explanation.

And there is a quieter lesson underneath all of it. The instinct that made me good at my work, taking something chaotic and giving it structure, was still there the whole time. The relaunch did not take it away. I just had to point it at my own situation for once.

Where it stands

trajecktory is open source and still evolving. So am I: still searching, still adding to it, still learning from what works and what does not. This is not written from the far side of the story with everything figured out. It comes from the middle, which is where most of us actually are.

If you are in your own version of that quiet right now, here is the one thing I would pass along: find the piece of the problem where your instincts still work, and start there. It will not fix the market. It will not make the search short. But it will remind you who you are while you wait for the market to catch up, and some days that is the whole game.

If any of this resonates, I would genuinely like to hear from you. You can connect with me on LinkedIn, follow the build as it goes, or look at the code on GitHub.