Derrick Hostburner, AKA Web Dude
System Administrator of Plastroltech. Quite competent with computers and has a full grasp of the concepts and skills needed to execute his job. Derrick is also very lazy and avoids taking responsibility for anything if at all possible. Frequently plays video games during work hours, sometimes even as he claims to co-workers that he's working.
- Brilliant, but Lazy: He's plenty knowledgeable about computers and is capable of doing all of his tasks as Plastroltech sysadmin, but he simply doesn't care and would rather play Halo or Nethack whenever possible.
- Jerkass: Mostly. He ignores work until pressured by someone demanding that something get done, avoids responsibility or deflects it to someone else whenever possible, and clearly no longer cares about his job beyond the minimum it takes to not get fired. Frames Chip for a virus attack to cover up accidentally resetting every password in the enterprise, which results in Chip getting fired.
- Only Sane Man: His co-workers include a pair of idiotic sales associates, a bitchy sales director, a director of IT who seems to know nothing about IT, a data center manager who cares about work even less than he does, and a stoner who works the nightshift. Of the characters we've seen, only Daryl seems to have a level head and enough knowledge to do his job effectively. Derrick may not be a good worker, but he's got more competence and does more good than most of the rest of the characters we see combined, and at least seems to be well-adjusted.
Chip Morehead, AKA Sales Guy
Sales Associate at Plastroltech. Similarly lazy (though more excited about his job), Chip proves to not only be completely inept at all things computer-related, but also a complete imbecile in virtually every way he has been shown in the web series so far. Was fired after episode four after releasing a computer virus on the Plastroltech network that shut down everything at the company for a day (the virus was a cover story for Derrick's mistake), and is currently working as a comically overwhelmed System Administrator at another company.
- Blatant Lies: Does these a lot, often for no reason, and doesn't seem to pay much mind to actually making the lie believable.
- Sales Guy VS Web Dude - Derrick accesses Chip's computer through remote desktop and sees dozens of open windows, including inappropriate websites, Solitaire and Freecell games, and other such meaningless programs. Chip insists that the windows are all for his work even as Derrick is looking right at the screen and can easily see it's all garbage.
- Excel Hell - Tells Ricky he was working on a sales report when he was just playing Wolfenstein 3D, which is somewhat strange given Ricky wouldn't have cared what he was doing. Later, tells Derrick he didn't download the virus attachment even though he definitely did, then a few minutes later admits to it as if he doesn't care whether or not Derrick knows.
- Chip The Sysadmin - Denies that he got fired from Plastroltech to Derrick, even as he looks through texts from Irving saying, in no uncertain terms, that he has been fired, and minutes later admits that he has a new job.
- Too Dumb to Live: His idiocy goes beyond simply being clueless about technology.
- Retro Gaming: Might be this, as he's playing Wolfenstein 3D at the start of "Excel Hell", in contrast to Derrick playing Halo in "Sales Guy VS Web Dude". Might also be just because he can't upgrade his computer since he can't handle any change.
- Walking Techbane: Oh, yes.
Sales Director of Marketing at Plastroltech. Started out as a minor side character, is now one of the primary characters in the series. Got married prior to the events of episode four, and is pregnant as of episode 4.5. Developed a very antagonistic relationship with Chip.
- Ascended Extra: In The Website is Down, was just a voice talking with Chip during his phone call with Derrick. Makes a blink and you miss it sort-of cameo in "Excel Hell" as an email in Chip's Outlook folder asking about his bad sales numbers and implying his termination is imminent if it keeps up. Gets assaulted by Chip in "Remain Calm". By "Sales Demolition", she's one of the major characters in the series, and this continues in Chip the Sysadmin.
- Characterization Marches On: In episode one, is having a conversation with Chip that indicates the two are at least on good terms, possibly friendly. In episode two, she sends Chip an email threatening to have him fired for poor sales numbers in the recent quarter. In episode three, Chip throws broken computer pieces at her and she gets a security officer to tackle him. By episode four, she clearly has distaste for him, not helped when he attempts to peek up her skirt while plugging a projector in underneath a table. In episode four and a half, Chip attempts to get an upskirt photo of her at a coffee shop, and Derrick mentions that he knows that Nancy hates Chip's guts.
- Department of Redundancy Department: Changed her name from Nancy Johnson to Nancy Johnson-Johnson after marrying someone with the last name of Johnson.
- Viva Las Vegas!: She went to Las Vegas for her honeymoon, referenced in her conversation with Irving at the start of Sales Demolition.
Director of Information Technology at Plastroltech. Derrick's immediate boss, Irving mainly serves to tell people what should be done and berate them for making mistakes. Also exhibits a lack of knowledge at things computer related, though not quite as bad as Chip.
- Face Palm: Gives a webby-winning (in-universe) one in the webby episode after seeing Chip's desktop.
- Kicked Upstairs: The only explanation for him being the Director of IT and outranking the considerably more competent Derrick.
- Pointy-Haired Boss: Probably. Keeps leaning up close to the webcam whenever he says something to Derrick like he needs to have his mouth right up to the microphone, has difficulty setting a projector up to work with a laptop, and is completely clueless when Derrick admits that he reset everyone's password by accident using mild tech-speak.
Lazlo, AKA Data Center Gangster
Data Center Manager at Plastroltech. Rivals Derrick in terms of laziness and disinterest in his job. Lazlo works out of the server room at Plastroltech and is called by Derrick whenever there's a question concerning what's happening with the servers. Has what appears to be a vitriolic, but somewhat friendly, relationship with Derrick, and is at least somewhat competent at his job.
- Bystander Syndrome: Hangs up the phone call with Derrick in Sales Demolition as soon as he figures out his issue doesn't involve him, saying 'this is not my fucking problem'.
- Only One Name: Has no last name listed on Derrick's phone contact list, the only person shown not to have one.
- Poor Communication Kills: Can barely hear Derrick on his cellphone while trying to reboot the web server, leading him to accidentally power off the Exchange server before getting the website's server.
Network Manager at Plastroltech. An elderly Texan, Daryl is the only character in the series so far who can understand computers on the level that Derrick does and displays a knowledge of technology that would be described as even average.
- Reasonable Authority Figure: Seems to be this. He realizes that Derrick is a capable sysadmin who shouldn't be fired over a simple mistake and/or that the Single Sign-On Server was set up in an incredibly stupid way that would inevitably lead to someone clicking the recompute button, so he tells Derrick to fake a virus attack to avoid getting fired. Or more likely he just doesn't want to deal with the additional workload and finding a new sysadmin."No no, you ain't getting fired for this 'cause then I'll have to deal with it."
Corey Kush, AKA The Nightshift Hippie
Nightshift watchman of Plastroltech's office. A stereotypical hippie, complete with a reference to attending Burning Man and possessing a Graphix Bong, Corey dropped the power caps at Plastroltech during his watch one night in an attempt to conserve power and caused some difficulties for Derrick the next day.
- Meaningful Name: Kush, of course.
- New-Age Retro Hippie: Takes up less than a minute of total screentime in the series, and yet there's a reference to him attending Burning Man, owning a bong, being zoned out during a conversation, having a friend named Candle, and dropping power caps to conserve energy at Plastroltech to help 'save the planet'.
- Small Reference Pools: Very few people are going to understand the significance of him groaning "My Graphix!" during his phone call with Derrick. Graphix is a brand of bong.
- The Stoner: In Sales Demolition, Derrick calls him in the middle of the day to reprimand him for dropping the power caps. Corey works the nightshift, so the middle of the day is his middle of the night. The call wakes him up, and Derrick puts him on hold. Apparently, the first thing Corey did, after being woken up in the middle of the night by a phone call, was take a hit off his bong.
Information Technology Support at BoZargs. Is being forced to purchase and install a product from Plastroltech by his boss, but knows full well that the product is useless.
- Deadpan Snarker: Has no problem being sarcastic, rude, and completely honest with Chip during his attempted purchase since he knows the software he's buying is a piece of shit. Even more so when Chips reveals himself to be an idiot and completely inept at computers.
- Genre Savvy: Knows full well that the Plastroltech product he's buying is worthless, but his idiot boss, 'who knows nothing about IT', read an article about it in Blight magazine and is now forcing him to buy it.
Sales Associate at Plastroltech. Appears during the first couple minutes of Excel Hell when he calls Chip to inform him about an email attachment he sent him that is actually a virus.
- Walking Techbane: Was stupid enough to run a 'MILF on MILF' program he got in an email, which of course infected his computer with a virus, so he certainly fits here.