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I’ve been working IT at small and mid-size businesses for the past 15 years, at the same place for nearly the past 12. I helped us grow from a “mom & pop” operating out of a converted farmhouse into a $20 mil regional powerhouse, the largest vendor for our products in the region. I guess I did my job too well though, because with the technology I provided, and a whole lot of really decent, hard-working coworkers, we got too big and were bought out by a large national competitor. Now I can see the writing on the wall, the company that purchased us has fired many of my coworkers already, a bunch of them on Christmas, and they’re rapidly shutting down our advanced technology projects that allowed us to be so successful. They’re keeping me around to finish shutting down our systems but even if they offered, I wouldn’t want to move to their corporate headquarters many states away.

When I got this job I was called by having my resume on the local Craigslist. The job I had before that, the same way. And also the job before that. Now I’m trying to scout job boards like Indeed and CareerBuilder, and I see plenty of listings from Boeing, and General Dynamics, and the huge defense contractors in our area, but nada for SMB’s. So for those of you working in SMB IT, how did you find your job? My usual approach doesn’t seem to be working. I love the feeling of “wearing many hats” and working for an agile small business, as opposed to being “just a number” at some corporate office. But where do SMB’s find their IT staff these days? Is it just blind luck pitching in with an MSP and hope someone decides to hire you on full-time?

Would love to hear some uplifting stories. Thanks! :slight_smile:

7 Spice ups
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I first completed a diploma in information technology (networking) and CCNA, my first job in IT was at an MSP, this was through a friend referral at the time.I find linkdein helpful to find a job these days and from the usual job advertising sites, you can also try giving out your resume to recruiters.

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Look toward MSP they will handle SMBs

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Our job postings go to Craigslist. We also work with recruiters.

Good luck!

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LinkedIn is pretty popular for job postings too

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Small businesses are almost completely owned by MSPs now.

Medium businesses are usually some mix of in-house IT and MSP (like ourselves). I mean we have a dedicated development team and some Cisco expertise, as well as 2 dedicate folks to do Systems Admin stuff (backups, upgrades, moves/adds/changes to phone etc)… but when it comes time to revamp our SAN, or forklift upgrade our switchgear/routing we work with an MSP. We’ll likely do our own hybridization of Exchange, and migration to O365, but some hardware stuff goes out.

I started with the company as the sole IT guy in 1999. I heard about the position from a friend. That friends wife worked for one of the companies I am responsible for supporting now. My friend and I worked on projects together at the Telephone company engineering firm together, one of our projects was to manage the IT roll-out of a regional bank (5 locations). We were really just the computer installers for that project. What we did back then was sold 3Com switchgear (because our other arm in the Telco back then was an ISP, so we were a Gold certified 3com provider). Anyway, after working on a few projects together I got noticed by several people.

So what I am saying is the relationships you build in the industry are the key to getting new positions.

Your CDW rep, your Dell Rep, your account manager with HP, your MSP contact, the guy you go to for larger projects stuff, your local Cisco Rep, all of these people bump into literally hundreds of other people in IT daily. Those are the people you need to stay close to. They will be your advocate if you let them know you are looking.

Linkedin, Indeed, Careerbuilder, Ziprecruiter are your friends. Keep in mind all of the above use resume indexing to find you “job matches.” This makes it very much like a website google indexing game. Trick is to pad your resume with the right info (in the right format), but not to make it unreadable, or irrelevant. So put down what you do, how you do it, and the systems you interact with daily. Also it may be time to call on some “friends.”

Final say. I think most SMBs are ditching the internal IT. I also think long term it is the wrong move. IT needs to be integral in the day to day of any business. I’m not bashing MSPs they are important to support the smaller staffs of the smaller business, and that relationship helps even into the medium business. Those of us who work with MSPs need to take a different attitude with them and embrace what they offer, and use them as extended staff when things get busy.

Obviously you could move to an MSP as well.

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Word of mouth is how I went from an ITSP to a SMB.

To be with that company pretty much from the ground up to multi-regional - wow! What a ride that must have been! Does really stink to hear what is happening though. I wish you luck in your future endeavors.

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I somewhat started sliding into SMB IT when I worked for a small restaurant. It was a small place with 3 computers, one was a register. We had a pair of back office computers on a LAN. I hooked them up so they could print and share files, and operate Quickbooks, and share the dial-up internet from the main computer.

From there I got snagged to work for a truck brokerage doing about the same stuff. Just managing the network printing, file shares. I learned Dataease the hard way when it crashed and lost all forms at 4:30 pm, data was still there just the forms were lost. When a restore wasn’t feasible since we had a day’s worth of data to re-enter, I worked till 3 am to rebuild all the forms. I played gopher when computer stuff wasn’t needed, handled accounting queries for AP. I managed the change from 6 dialup aol internet accounts to 2 way satt internet. Managed their phone system changes. Handled all their load postings every night on several platforms (cleverly abusing html to do so as fast as possible)

I wandered away from computery stuff for a 5 year stint at Walmart, and then worked another year in the warehouse before sliding back into IT as point of contact while doing a data entry job/receiving clerk for a few years. The company had 1 site, then 2… then bought 2 more. IT got started at the same place after the 4th site was bought and I was told “You’re POC for the MSP’s, go tell the new IT director what you know”. I spent my afternoons after my regular shift chatting with the guy. After the 2nd afternoon he told me I had given him more information about everything than anyone else who actually has admin passwords. Then he asked me “What are you doing not working in IT?” and offered me a job. 6 or 7 years later still here! Different office/site but I’m handling all the network, hardware, VM, server, and services stack.

It’s funny years ago I feared working in IT I would lose interest in computers. I’m still a fanatic. Probably worse than I had ever been before.

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I literally got offered a job right as my internship was ending because I apparently proved that they needed the extra help. Otherwise around this region it’s really just a lot of recruiters and sending your resume in to anyone who might be looking.

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Found my current job 2.5 years ago on craigslist. I’ve been in SMB for 20 years. Keep your eyes on every job board. Usually a SMB will pick 1, maybe 2 free or cheap places to post job announcements.

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I went through that for the Last Time in December of 2000. (For a born-again Southern boy, Rochester, NY = “Lake-Effect Snow” = HELL no.)

It was the 4th or 5th time I’d been put on the street by the death of my employer through no one’s “fault” (but it happened anyway).

I did the usual recently-released things until Y2k didn’t happen and then 9/11 did, and “employee” jobs vanished where I live. I refuse to debase and humiliate myself by peeing in a cup for some Hater, and I am quite happy living where I live, so I did whatever I could get paid for to keep the bills current & try to get “back on the horse”. Nothing helped, including the government “Job Service” BS. Don’t waste your time there.

It turned out to be the Very Best Thing that ever happened to me in my entire Life (of several careers)!

One of the gigs i picked up (from Craigslist, coincidentally) introduced me to “Freelance Boards” and I have never looked back. Being a small Southern town, we don’t have much “computer” work here, but I have a good car (and plenty of previous-career experience keeping it running) and love Road Trips; so I cover 3 states for “on-call smart-hands” gigs and Love Every Minute of it.

I’m not “self-employed” (that’s a legal-status term with a specific meaning); I “work for myself”, which means I am FREE to do what I want & get paid fairly well for it. I choose the Work Orders I take (if they don’t want to pay, I don’t offer to play), do an AWESOME job for the “Buyer”, get on “Preferred Vendor” lists all the time; and generally don’t remember what “stress” felt like. Paying my own taxes, insurance, mileage, meals, etc. and funding my retirement are a chore and a duty, but (it turns out) that’s so easy I can’t believe I haven’t worked this way my entire life.

Many of my “gigs” have turned into “long-term engagements” with billing rates that make me very happy (and highly motivated to Do Good Work) and the work itself (since I have plenty of experience) is, often-as-not, almost trivially easy.

If you feel a “Need to Belong”, stay the hell away from “Freelance Work”!! You’re the Lone Ranger, sweeping in to kill off the Bad Guys, tip your hat to the school-marm, collect your bag of gold and ride off into the sunset. Likewise, if you need to Google answers (especially "How do I get the Internet back up so I can Google “How to get the Internet back up?”) you’re not going to make it in this world. OTOH, if you have “the skills to pay the bills” & a Work Ethic to match and want to be treated as a peer, a valuable ally, a “go-to guy” for a raft of different, interesting, brilliant people in many companies from all over the world, maybe this would be useful to you?

HTH, Oldsmobile_Mike…

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I found my first real IT job by calling all the computer service companies in the Yellow Pages (remember those?) and asking if they are hiring. I called about 20 of them, maybe 7 had me send resumes, and I think only 2 called me back. One of them (the very first one that I called that day) was a small shop with 2 techs and the owners/sales guy. One of the techs quit that morning and they had a big network cabling job starting that week. I interviewed the next day and started that afternoon. I chalk it up to being in the right place at the right time. I worked there for almost 6 years. I started as a PC/printer repair tech and the company grew to specialize in POS software, and by the end I was handling all the POS implementation projects.

The first few years of that service job were part-time, so I found a second part-time job doing tech support for a local dial-up ISP (remember those?) I found that job because a friend worked there and it was down the road from my other job, so I would occasionally drop in to shoot the breeze. I got to know his boss a little bit so when my friend went on vacation for 2 weeks his boss asked if I would cover for him. I ended up working there part-time on a regular basis. I started as simple tech support and grew in to a network/system admin and did some neat projects like coding a custom dial-up billing integration. That ISP was bought out by another slightly larger one, so we all moved over to that company and I continued part-time. I ended up working both these jobs part-time for almost 2 years, until the service company asked me to go full-time.

After working full-time at the service company for several years, one of their customers approached me and said they were going to be hiring a full-time IT person to replace the service company. They offered me the job. I wasn’t completely happy with the service company, the pay still wasn’t great and the customer was offering a good amount more, and I didn’t have a non-compete or anything, so I jumped at the chance. The company was relatively small, roughly 20 people in the office, so I was “the IT guy” who did everything. Over the years the business grew and I learned lots. During that time we added a second IT person who reported to me and he handled a lot of the front-line support so I could focus on IT projects (and enable me to real vacations.) I also became very involved in BI/data analysis projects, process improvement/automation, ERP system customization/integration, etc. I worked there for 11 years.

While working that job, I did the odd bit of IT work in the evenings and weekends. Over the years my name was passed around to various people/businesses and so I had this “side hustle” which I partly did for enjoyment/variety, partly to keep my options open in case my day job ever disappeared, and the extra income was nice. Over the years this side hustle grew and started consuming much of my free time. I was getting to the point where I had to start turning away extra work or make more time for it. After a lot of consideration, I decided that becoming a full-time consultant was something I really wanted to do. I enjoyed being exposed to different environments all the time at the service company, learned a lot of real business skills from my long-standing day job, was growing bored with some aspects of the day job, enjoyed working with a lot of external consultants in that job, had a lot of business contacts, and had people calling to offer me bits of work. I eventually made the leap and as of a month ago I officially became independent, with my old day job as one of my clients. I’m only a couple months in to this adventure but it’s been quite enjoyable. I’m mostly focused on SQL database/integration and process improvements, some networking projects, and some traditional IT break/fix work

Having contacts makes a huge difference in finding a job. Almost every company would rather hire someone they know or was referred, over some unknown person who came in through a job posting. But also try cold calling some local businesses - you might get lucky, and it avoids being buried among the dozens/hundreds of other applicants on a posting.

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I’d love to hear a bit more about this. Can you give an example of a long term freelance job you’ve had? Would this be a situation where you had to live out of hotel for a while? How does work like this affect your family life?

@jimlong3

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It’s hard to answer that question. I mostly just take "commute-able’ jobs so I get to be home every night (and most afternoons). Most of the work I get is “two-a-day” calls, so that’s the opposite of “long term”. (I set my quota to a certain amount of money I need to bring in per week, which means I can stand 1-call days or 3-call days & they all work out at weeks-end.)

Long-term gigs “just happen” – sometimes I only see them in retrospect. E.g. swapping Routers for a new Lunch Store chain’s stores nearby got me into almost all their stores in the State, eventually. Then there’s the kiosk work, which is another one that started with one at a decent bill rate, then ended with me having keys to all of them & being the “preferred vendor” for my area.

I once got to run Dell Warranty calls for a decent overall rate (they were all the same laptop, all in batches, all in schools) by requiring that I would only roll for them if they could guarantee me a minimum of 10 laptop repairs per day. (I knew how pitiful the per-device rate Dell squeezes out to their end-workers so I stuck to my guns & got what I needed) Since the kids in the schools were less than motivated to take care of their “free” laptops, a 10-ticket day was “light”, but I got to sit my butt in one chair, depot-fashion, and process laptops in batches from one side of the table to the other, All Day Long. Glorious work, that, until the contractor who brought me in got in trouble with Unisys & we were all sent away.

Once I got to go to a metropolitan center 2 states away for 2 weeks to cover for a POS service tech who needed a break. That was fun; I told the hotel I needed Internet access, but I only had a wired computer. The only room that had wired Internet just happened to be next to the pool!!! SWMBO went with me, but not as a co-worker, just someone to watch the room while I ran calls. Not relevant, okay… Since it was just “on-call, ready” status, we got to play Frisbee golf, swim, sight-see, etc. as long as I would “stop, drop & roll” when the buzzer went off. Since the guy I was covering for was Very Talented, that buzzer was pretty quiet. (Fun tech there, too – loved soldering chips and connectors on an antique POS system on the counter in front of their customers… During a thunderstorm, no less!)

Another time, I took a Work Order for cabling help, which led me to meet the crew chief, who called me back after the WO Buyer went under. This project was converting the biggest building in my town from a hotel (failed) cum office-space (failed worse) to a dormitory for the local State College (still struggling). That led to me rolling in SWMBO as labor for many months, as well as getting a friend on the crew for a month or so. We followed the framing crews up the building, installing miles of Cat5e & RG6-Siamese cables on every floor; then we went back through installing WAPs, Routers & Switches and Cameras & DVRs, then stuck around for troubleshooting & punch-list. A year later & the #3 man on the corporate totem pole was calling me in for all sorts of high-tech help like pulling fiber, finishing a Jumbotron physical installation, getting it working then effecting repairs over the next year or so, etc. Loved every minute of that gig too! Well, except for the fire clay… SWMBO helped with that (and we got “exception” treatment carrying ladders up & down in the elevators which pissed off the General Contractor’s help), but I still hate fire clay.

I’m trying to think but nothing’s happening. There were other multi-week gigs, but the main point is, I take the Work Orders with an acceptable Spend Limit/Bill Rate & see where they end up. I always do Good Work so if there’s any more “meat on the bone”, the Buyers are usually happy to keep me around awhile.

Anyway, the last 19 years have left me with a lot of these stories, but the hour is nigh and I must away. TTFN…

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Quite interesting. Hearing these stories makes me miss the variety of work I was able to do at my previous job (an ITSP). Being able to put your hands on so many different types of tech can be a great thing. Thanks for posting these.

Do your work orders come from one central agency? Or are you truly on your own and you just take jobs as they get posted (perhaps bidding for them)?

@jimlong3

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The “platform” (a WWWeb site) is like a clearinghouse, a proxy, or a broker. Work Orders are “bought” (with provisional qualifications like skill sets, background check, proximity to the work, etc.) by “Buyers”, the platform pushes them out to any “Pros” (short for “Service PROviders”) in the area who have posted matching skills or qualifications on their Profile, and it’s “catch-as-catch-can” from there. The “Pros” either ignore the offer, make a counter-offer, or accept it outright; then the Buyer picks from the list of replies. The Work Order isn’t “entered” into the system until the Buyer pays the Spend Limit in escrow & when the Buyer approves that the work is done, the “platform” cuts the check (not on paper unless you ask for it). Any disputes are handled by the “platform”, usually to the Pro’s favor unless the Site Contact has anything to add.

The only real “negatives” I have are the lack of work in my area (not that much going on around here), and the fact that some “Buyers” seem to think I’m some incompetent miscreant hiding in the basement looking for drug money so they don’t offer (or accept counter-offers of) anything like “prevailing rates” in my area for the Scope of Work they propose. Eventually “those” Buyers either get no help at all (or “get what they pay for”), are disappointed, drop off & are never heard from again. Self-correcting, just like Liberty and Free Markets always are.

PS: “Being able to put your hands on so many different types of tech” is absolutely “a great thing”, but these “platforms” are not the place to acquire that!! If you really want to succeed here, you need to bring that experience to the table, not expect to take it away.

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All I meant was that it makes this line of work fun and interesting vs. working for a single entity with technology that rarely changes.

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The closest I ever came to SMB work is working with a team of 4 that service veterinarian’s offices. I’ve interviewed at a number of them, and repeatedly it has looked like soul crushing work that involves a whole lot of “answer the call, service the client, bill for time” work that just seems like a huge drag. The people that I know that are successful are the project team guys, but I’ve never been able to get interviews on those teams.

I’ve heard that kind of work isn’t for everyone, and maybe it will be for me one day as well, but you seem to be doing very well at it.