Stranger, I'm sure Kevin will have some excellent advice for you on this subject.
If I may offer some advice to the young man you are referring to as another young person trying to break into the NFL Front Office going into his Senior year in college, it would be this:
1. Attain as much meaningful work experience as possible and play/be around the game for as long and as much as possible. Don't be afraid to start looking for meaningful work experience in high school, it will only help.
2. Network as much as you possibly can. The key to this business is getting your foot in the door which is also probably the most difficult part of it. If you don't have a family member/close friend with strong connections to the industry, aren't a former player and aren't a former coach, you are going to have a difficult time getting your foot in the door. However, I did say difficult, not impossible. You just have to be willing to put yourself out there and go after it. You'd be surprised at how many of the guys in NFL Scouting departments around the league and Front Offices as a whole are willing to speak with you and give you advice if you put yourself out there and seek it.
3. You're going to have to be able to deal with rejection. I have NFL internship experience and have been working hard to get a shot at a scouting internship. Thus far, I've been rejected around 80 times over the last 2 years. It is going to happen to just about everyone. It is a real challenge. You have to be able to get past it, keep fighting and not get discouraged. I am a self-confident person and very driven but I would be lying to you if I said that I have never been discouraged. There have been letters/emails that I received from teams that I felt I had a shot with rejecting me and it really stung. Luckily, I have two great parents that have always been there to help me get back up when I have been knocked down. And I will keep fighting for this until I get an opportunity. You have to have that sort of mind-set if you want to get a shot.
4. Once you get an opportunity, be ready to work. The hours are going to be intense especially as an intern. They will work you hard and they will work very long hours. If you get that opportunity to prove yourself, don't let it go to waste. The hours will likely be brutal but it is all worth it in the end. Don't be afraid to ask for help or make mistakes. Just do your best and be accountable for the mistakes you make. As an intern, they're pretty understanding because it is part of the learning process as long as you are willing to take responsibility, fix your mistakes and do not keep making them.
5. Finally, don't take any opportunity for granted. If you receive a chance to work with your college team or work with a camp or something else, you never know what sort of connections you might make and things you might learn. Try to learn as much as possible and try to meet as many people as possible.
That's all I have for you now, Stranger. Hope some of this helps the young man that you are talking about and I hope he gets his shot in the NFL. I wish him the best of luck!
Jerry