Context:
I had interviewed at a company several months ago and the recruiter and CTO liked me and added me on LinkedIn. Didn't get selected for the initial role due to being a bit green for the level, but they said to keep an eye out. Flash forward to now, there's a new role open that I applied to that's definitely in my scope of experience.

My question is: should I reach out to the recruiter or CTO, and if so, how should I approach?

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Absolutely reach out, getting a job nowadays is all about connections. If you applied to that job you will just be another applicant thrown into a pile. If you are able to have him as a reference you will instantly go to the top of the pile. Reach out and send him a message over LinkedIn. Make it just a friendly hello maybe just reminding him of who you are to rejog his memory, don’t mention the reference. After he replies the next message or two you send him ask if you could use him as a reference when applying to the job. Don’t go straight into the reference, start off with a normal businessesc conversation. I did that same thing and landed my dream job.

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Update: I got the job! I start at the beginning of the month.

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