Should I / How to reach out?

I’ve come here looking for advice again for my job search.

So a year ago I emailed an alumni from my unversity looking for some resume advice. He responded favourably, saying I should quantify tasks and when he looks at resumes, he is looking for at least CFA level 2, etc.

Then, just last week I saw a job posting at his firm for a junior position, which I really want. Would it be okay to email the alumni again asking for the hiring manager’s phone number and email? I haven’t developed any rapport other than the email I sent. Would it seem like pestering and annoying? I want to be proactive in my job search. I feel like I am qualified for this position since it is junior but since online applications have such a low success rate, there is a chance they won’t see it.

obviously

email the alum and let them know you are interested in the role and think your x y skills and experience would make you a great candidate, ask if he could provide an introduction to the manager to chat about the role.

he will do one of the following a) ignore you, b) put you in touch, c) recommend you.

yes