Since finishing I've worked at a single org (5 years). I've become far too complacent because our projects have mostly been internal projects. I have worked in an ecommerce type company before masters (5 years), but it was before clouds were mainstream, and the traffic was in thousands daily, not millions.
Lately, I've been thinking about my career, and it seems I'm at a deadend. There's no way to progress at this current org, since it's quite small. The income is not bad, but I feel it's not a very secure position due to the current situation. I would like to interview at bigger companies, especially Microsoft since that's the tooling I have most experience with. I wouldn't mind prepping 6 months on the side using cracking the coding interview, leetcode, etc. but I feel like I will be judged too harshly due to my lack of progress in my career during the last five years. I haven't worked on large, scalable, fault-tolerant, kubernetes, kafka messaging, insane-state-of-the-art type of systems.
Is anyone else in a similar position? Any advice?
All of that is mostly made up. The world runs on pretty mundane software.
You seem to have internalized a few aspects of the software culture that are not constructive. Writing software is a fine job. No one can tell you if you have "progressed" enough or not and "hyped" technology should not be the metric you use to judge yourself.
I would recommend reading “So good they can’t ignore you” by Cal Newport to get realistic advice and strategies for career advancement.
For example, firstly you need to be clear about whether you’re in (or want to be in) a “winner takes all” market or an “auction” market. The strategies for building “career capital” are completely different for each.