Assuming I find the contact information for the hiring manager, should I try and connect with those that work for him or those more senior?

Original Question: Assuming I find the contact information for the hiring manager, should I try and connect with those that work for him or those more senior?
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FINDING THE HIRING MANAGER
If the hiring manager is not specifically identified - three ideas
1)Start with a note into the HR group to clarify the reporting structure
2)If you know the title, not the person - use Advanced Search on LinkedIn to find them
3)Use your network to get contacts inside the firm to help figure it out.

CONNECTIONS AROUND THE HIRING MANAGER
I would try to connect with people who are senior, peers and direct reports to the hiring manager.

All Contacts: Help them understand the 2-3 key experience points on why you can accomplish the role's objectives. Keep it to 2-3, because it gives them a simple 'pitch' to share internally - also people will not remember any more. Focus on outcomes acheived in the past (e.g. raising capital, overseeing merger) that are relevant to the company, not specific skills.

Here's are the key items I seek for each type of person:

Senior: What are objectives for both themselves and the hiring manager. If you can show the hiring manager how to meet their goals, beside how you can perform within the role, that's a big win.

Peers: Objective view of what the finance function is doing well (or not) and what they need from finance to help with their success.

Direct Report: How does the hiring manager run their group (philosophy of their role in company, style, etc.). What are the key initiatives within the group - both current and expected. Lastly, what are their objectives/goal - this will be your peer, so if you have experience that can help them - that's another big win.

ENGAGING THESE CONTACTS
Usually you get these connections via your network. I have always positioned my request to seek their insight into the company's culture and objectives.

Before you meet each person, figure out if there is an idea, connection, etc. that may be useful to them. If so, get it on the table straight away when you meet - it really changes the tone of the meeting to one of offering mutual assistance.

Hope this helps.

Mark