How to reconnect with a Director?

Current analyst that connected with a BB managing director on LinkedIn. We both went to the same non-target state school and we both share the same ethnic background. I felt that he really liked me and we connected a lot. I messaged him on LinkedIn a few months later but he never got responded (I chalked it up to him being busy, as MD's routinely are). I would like to connect with him again as I started a new job a few months ago and would love to update him on that and speak to him again. How would I go about connecting with him?

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