Dirty IT job No. 3: Enterprise espionage engineer (black ops)

Seeking slippery individuals comfortable with lying, cheating, stealing, breaking, and entering for penetration testing of enterprise networks. Requirements include familiarity with hacking, malware, and forgery; must be able to plausibly impersonate a pest control specialist or a fire marshal. Please submit rap sheet along with resume.

Social engineer, con artist, penetration tester, or white hat hacker — whatever you call it, Jim Stickley has a dirty job that actually sounds like fun. As VP of engineering and CTO of TraceSecurity, Stickley gets to talk his way into a client's offices, sneak into their data centres, make off with the company's vitals, then come back later to show them where their internal security broke down.

The best part? He gets to wear disguises. Pest control specialist, AC repairman, OSHA inspector — Stickley and his crew have a closet full of uniforms. But fireman is a particular favourite. "At one place you're the fire inspector, and girls fall all over you," Stickley says. "The next place you're wearing the pest inspector suit and you're the scum of the earth."

First, Stickley and his team take over the company's e-mail system and schedule an appointment. Then they show up in the appropriate fake attire. Whoever has been assigned to watch them usually leaves after about five minutes, Stickley says. If not, they send her out to get them coffee or offer to show her a (fake) dead mouse they found in the corner. That usually does the trick.

Once she's gone, they sneak into the security room and take all the backup tapes, load Trojans onto the servers, or plug wireless devices into the network and hack it from the parking lot.

"If we can get the backup tapes, we're done," Stickley says. "Every piece of data you'd want — mothers' maiden names, Social Security numbers — is on those tapes. We've also walked out with computers, boxes filled with loan documents, and applications for patents that have been drawn up but not submitted. It's amazing."

Stickley says he's penetrated more than 1000 locations and has yet to be thwarted. The dirty part: Coming back the next day to face the people you just owned.

"You feel dirty, if nothing else," Stickley says. "People come up to you and they're mad. 'I can't believe I got you a cup of coffee.' But ultimately you're just trying to help them out. Nobody gets fired for screwing up. The whole point is to learn from the experience."

There's at least one person who doesn't gain much from Stickley's exercise in creative insecurity, however.

"I feel really bad for the real pest inspector," he says. "The next time he shows up, boy does he get beaten down."

Dirty IT job No. 2: Data centre migration specialist

Position involves relocating and reconfiguring data centre over impossible distances within a ridiculously short time frame. Prior experience as cable jockey, rack-n-stack grunt, console monkey, and/or log zombie a plus.

Moving a data centre is a dirty job. Moving one halfway across the country in 48 hours — that's a really dirty job. But that was the task facing Scott Wilson and his firm, Marathon Consulting, when one of its clients needed to close down its Chicago data centre the day before Thanksgiving 2003 and open for business in New York the following Monday.

Wilson tried to persuade his financial services client to set up a duplicate centre in New York; they could power down the Windy City operation, light up the Big Apple, then gradually move equipment as it was needed. No good, said the client — too expensive. So at 4:30 p.m. on Wednesday, his people loaded roughly 80 machines into trucks and drove nonstop to New York.

"We tracked the trucks using GPS, so when they reached the Holland Tunnel, we went to the data centre," says Wilson, managing director of the Brooklyn-based Marathon. "We spent the next 48 hours setting it up and getting operational. But we got it up." Unplugging everything and cleaning out the muck that's collected over the years is bad, Wilson says. "Cables sit for years in half-baked air-conditioned rooms that are dusty and nasty."

But the worst part is putting Humpty Data centre back together again. "Most data centres aren't labelled correctly and have been put together by 10 different consultants and in-house employees who each have their own ways of doing things," Wilson says. "And recabling someone else's work is always fun."

Fortunately, migrating data centres isn't something firms do very often. But when they do, it's an ordeal. IT pros resent having to do grunt work, but they also understand it's part of the job.

"On the other hand, moving 10 racks of servers from Chicago to New York in 48 hours at the end of the day feels amazing," says Wilson. "The gratification is definitely there."