Starting in consulting to F500?

Networking into Fortune 500 from Consulting (Originally Posted: 01/12/2011)

I'm in a bit of a weird situation and am unsure how to proceed.

I graduated in June 2009 and immediately went to work as a financial analyst for a small consulting firm. Our largest client is a Fortune 100 company. My boss used to work for this company and has a bunch of contacts there. I would like to move into industry in a finance position, especially for this client. However, I'm unsure of the networking etiquette when trying to do so. For some background, we've spent a lot of time with two groups within this company:

Group A) Since I joined, we have worked with this team on 4 different engagements. I personally have not interacted with any of their team members. The closest I've come has been on calls (almost exclusively listening/taking notes) and being copied on emails. Nevertheless, I have spent significant time on their projects and think that they would recognize my name if they saw it. This group is headed by someone who used to work for my current boss (when she worked at this company) and they are still somewhat close and in contact, which is how we got this engagement. This group focuses exclusively on finance.

Group B) This group is in a completely different division and city as Group A. I have spent the past 9 months working on-site with this group 3-4 days/week, so I've gotten to know many of the team members very well. The individual I've been working most closely with used to work with my boss. Again, this is how we got this engagement. This individual is in a finance role, but because of the nature of the group many of my other contacts are in separate roles, in particular marketing and sales.

I recently became aware of a job opening with Group A that would be a great fit for me. I'd like to know how best to leverage my contacts to help me land it. Here are some concerns I have:

1) Is it appropriate to contact a team member in Group A, an active client, to express my interest? Again, I haven't interacted much with anyone in this group, although they would probably recognize my name and certainly my company and the work we've done for them.

Concerns: Would this be considered presumptuous? Also, since at least one person in this group is close with my boss, there is some risk that my boss would find out I applied. Pros: I could find out more info about the position and might have an advantage since I'm familiar with the group's work. Contacting them would remind them of this, although I'm certain they'd recognize this when looking at my resume since this engagement is included on there. Still, this would be a good way to stick out from the resume pile.

2) Would it be appropriate to ask one of my contacts in Group B (also an active client) for any help they could provide, particularly the individual whom I've worked most closely with and who is in a finance role?

Concerns: He is close with my boss.
Pros: He is in a well-respected position and has likely either worked with or at least knows some of the team members in Group A, so a recommendation would probably be a big boost.

3) Should I be concerned at all about my boss finding out that I've applied for a position? I just have a terrible vision of one of my bosses contact's in either of these groups calling her up and letting her know I've applied. That seems awfully unprofessional to me (and possibly illegal?), but my boss's contacts are somewhat professionally close with her. We're a VERY small firm and I know from a prior incident involving a co-worker that my leaving would be a major inconvenience and probably harm the business in the short-term since we'd have to take on fewer engagements. My boss's contacts in both groups may be aware of this, as well.

4) Does the fact that our engagements with these groups are currently ongoing change how I approach this? I wouldn't have any familiarity with this opportunity or my contacts if not for these engagements. Would leveraging these contacts violate some sort of professional etiquette?

5) On a resume, is it appropriate to list the company name when I describe my experience with Group A since the client is in fact the group I'm applying to? It isn't public information. What about listing the client name with the experience I've listed involving Group B? This is a separate division and city and again, the information is not public. The reason for doing so would be to add to my credibility since I've done lots of work for this company.

I have a feeling I'm over-thinking all of this. However, I've never been in this type of situation and don't have much networking experience, so I appreciate any advice anyone can give me.