A couple of years ago I saw a job ad that was a perfect match to my skills and experience, but I couldn't apply for it at the time (was on maternity leave). I have been checking the company website ever since, but similar roles haven't come up. Would it be worthwhile sending a speculative application to them to see if they might be interested, or would this ruin my chances further down the line if they advertised for a similar role again?
Also, at the time I sent an invitation to connect to the person recruiting (head of the department) on LinkedIn with a message saying I am not applying now but might be interested in the future. They accepted me as a contact but didn't reply anything. Would it be worth messaging them again, or just contacting the HR department?
I work in a very niche field so really can't afford to mess this up as there aren't many employers in this field.
I don't see why not! If I had necessary skills and experience. I would send in a (tailored) CV and covering letter to the HR dept and to the LinkedIn contact. Then I would try to follow up by phone. Why the hell not? This is an intelligent and completely appropriate strategy.