By saying my hint was "strategic", I was meaning that it wouldn't come completely as a surprise when I give them my 2 weeks notice.

I do the job of 3 people, and sit at the confluence of Product, Sales, and Customer Service. If I were to poof out of existence tomorrow, they would have to scramble to fill my role. If I were to poof out of existence at the end of January, the whole sales organization would be fucked, because that's when the "season" for my work starts, and it ramps up VERY fast.

But we get a TON of paid vacation in November and December. (One of the benefits of being owned by a German company, is they value their family holidays very highly.) I also have about a month of PTO available to me.

And this company tends to cut people out pretty quickly. Someone gives 2 weeks notice, and by the end of the day - sometimes end of the week - they are no longer in the office or reachable. There are some security concerns around our products and services that make it prudent for the company to disable the accounts of employees pretty quickly, rather than continue letting them have access to the company's data and resources.

So yeah... I think I'll give them notice on January 3.