Project Management (Score 0)

My suggestion would be to look for someone with structured project management experience. I am not necessarily referring to a "PMP", but more someone who understands how to approach things by developing a process. For the 200+ clients, the more information you know about them, the better you will be. There should not be much guessing about how much downtime will cost. They can tell you pretty close. Make sure that you are up to date on exactly the technologies that they are using. Install remote access capabilities like VNC. Install a modem at their rack if they have one. They will need a dedicated analog line for this. This allows you to get into their system even if their network is down. A VPN connection would also be a good investment for when their network is up IF you will be working on code. For simple setting changes, the modem should suffice and is much more cost effective. You are in business (I hope) to expand and make money. Two mistakes plague our industry. People try to grow in an unintelligent manner or they are afraid to grow and die. Grow smart. Take the clients if you are the type of person who can research and learn quickly. Hire a consultant for a 2 month gig to help you ramp up your systems to a more automated level. Put it in the contract that the consultant will fully train your staff on it. Then (s)he is off the payroll. An hire a PM who you can offload the research to. And most importantly, good luck and have fun!