I started out as very-entry-level phone support and worked my way up. Do you know anyone who works in IT who can give you a recommendation just to get your foot in the door? That's what worked for me.
JLee, have you written about that path anywhere? It's one my husband is currently in the relatively early stages of.
I started as an intern for a small IT company in September 2012. We were a managed service provider (MSP) primarily serving small community banks. My initial tasks were fairly simple; checking backup logs and completing task tickets was my primary function. I learned quickly and started taking phone calls as well and was promoted to what was effectively a junior help desk position in January 2013. I only did that for two months - in the end of February I was promoted into a normal help desk role. Also, during this time we were bought out by a huge company and started expanding even more rapidly.
To clarify what I was actually doing - our techs had effectively unrestricted access to customers' server environments, so the person who answered the phone could fix hung servers, Exchange/email outages, etc. We didn't have graduated access levels for that unless you're talking about network stuff (routing/switching) or the VMware infrastructure that we provided (we did have access to customer-provided VMware infrastructure). I worked in this position for 11 months and slowly transitioned into a backup for our technical lead during that time. When an opening came up, I was promoted to a technical lead (January 2014). I did this for seven months, learning more along the way (routing/switching, etc). In July 2014 I was promoted to our escalation/emergency team. Basically, we were three people working (or on call) 24x7 for emergency / high priority outages across 120+ customers (each with anywhere from one to dozens of physical locations). I was promoted again (from sys admin 1 to 2) in August 2015. In September, I was offered a position with a major company on the east coast, which I accepted.
My advice for him is to try to do the job above what he's currently doing. If he has a technical lead, work towards doing what his lead does. In my experience, trying to do the job of the person above you will demonstrate a willingness and ability to learn - and also an ability to handle the next step up the ladder. Also keep in mind that there will come a point where he will be better off to jump ship than he will relying on in-house promotions/raises. I'll list my salary history as best as I remember, using annual figures for each step (in reality my annual income varied from these numbers, since I never did the same thing for a full calendar year):
Sept 2012: $33,280, no benefits, intern
Jan 2013: $40k, plus benefits (medical, holidays, two weeks PTO), tech support analyst
Feb 2013: ~$43k, tech support consultant
Jan 2014: ~$49k, tech support engineer
July 2014: ~$57k, sys admin 1
April 2015: ~$58k (2% raise), sys admin 1
August 2015: ~$61k, sys admin 2
Sept 2015: $97k + bonus, four weeks PTO, HSA benefit, paid phone, far superior health plan, etc - technical manager / new company
I gave my notice the day of my 3yr anniversary, which was rather satisfying. :)
I had a wide range of experience with my prior company (VMware ESXi, Exchange, Citrix, AD/GPO, Windows server 2003-2012, Cisco route/switch, Cisco firewall, SolarWinds network monitoring, and many proprietary applications I'd be happy to forget about). Now I primarily deal with VMware, Cisco UCS, Cisco Nexus fibre channel, and I'm about to learn about robotic tape libraries too.
I did relocate from AZ to NJ for the last job, but fortunately I am able to rent my house in AZ to friends and I'm renting a furnished room from friends in NJ, so the financial impact of my move was fairly minimal. I decluttered/donated a lot out of my AZ house and "moved" via one-way airline ticket and two checked bags.
Finally - networking is how to move up. I almost didn't get my foot in the door three years ago, but I had a good friend who pushed hard to get me hired, and one of his managers agreed enough to give me the opportunity. He has this part done already - the rest of it is making connections and establishing a reputation of "that guy who wants to learn." If you have any questions, feel free to send me a private message!