Approaching a CEO on Chief of Staff Role

Was curious if anyone had been in this position before. I am targeting CoS roles & I ran across a startup that raised a huge B round (90mm plus) and is advertising a CoS role.

Their CEO and co-founder is an undergrad alum. Should I reach out directly to him on LI about the role or apply online & then reach out? I would never hit up a C-suite exec at an org this size, but the job literally will report to him.

Any thoughts on how to run this approach in the most strategic fashion?

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