I’m in a somewhat similar situation. Started my career 15 years ago as a dev, quickly moved to technical project management. Then I moved to infrastructure in

I’m in a somewhat similar situation. Started my career 15 years ago as a dev, quickly moved to technical project management. Then I moved to infrastructure in a variety of roles, essentially around management (of project managers, architects, HW engineers, etc). After 10 years of that, I completely switched tracks 2 years ago and became the CTO of a startup in the insurance sector. I joined as the first employee and the first IT person. Like you, I was worried about my lack of recent experience in development. I had to cram for the technical interview but it boiled down to architecture/dev best practices and talking about a small side project I’d done (to reassure them that I would be comfortable coding myself). After I got the job I spent a few weeks coding in earnest: nothing like the perspective of a new job to focus the mind! When I started the job, I quickly found out that although there was some coding involved, a surprisingly big part of it was very similar to my previous jobs: security audit, contract management, hiring... My first hire was a lead dev to help me with the back-end and to do the front-end. So, I managed a similar transition (although the circumstances are a bit different), it was easier than I expected, and I haven’t regretted it for a second. Hi for it! (If you want to chat, send me an email)