[robdimarco]

I have very similar experience. I'm 42, spent most of my career in startups / small companies in CTO-level positions, but last year took an engineering position in big tech (at one of the companies you mention).

My suggestion for someone with a lot of experience is to focus more on networking your way in to the company than on skills brush up. Find contacts at the company(s) you are interested in and try to set up direct meetings (in person, video conference) to find out more about positions, responsibilities, etc. at that particular company. Each company has their own unique philosophies and growth paths for individual contributors vs. eng. managers, so I don't know that there would be one generic piece of advice to follow.

Feel free to reach out to me at <username> @ gmail if you would like to talk more specifics.

[Rickasaurus]

As someone in a CTO position now but being a serious IC ~5 years ago, I'm curious. How was the transition back for you? I love my job, but I also miss it.

[robdimarco]

So far (been about 9 months), I like being an IC a lot. I still get to be a leader and mentor, but have a lot less paperwork to fill out come review time! I always enjoyed the coding part of the startup CTO job more than the manager part anyhow. I feel that if I ever want to get back in to management, either at my current employer or somewhere else, I'll be able to make that transition pretty easily.

But if I go full-time manager, I don't know how easy it would be to flip back to dev / IC.