The 10 worst tech jobs
Taking an objective look at the 10 worst jobs in technology
Last week, I took a deep dive into the best jobs in technology. They spanned a wide range of activities and backgrounds, but it got me wondering what the WORST IT jobs were. What are the jobs you don’t want to find yourself in?
If you tuned in last week, then you are already familiar with the ranking system I am using here. The goal is to create an objective ranking of different jobs in tech by evaluating the things that are clearly “good” or clearly “bad”. For instance, we can all agree that more money is better, so jobs that pay more are ranked higher. The visualization below examines the objective elements of a wide range of jobs in tech. Look for yourself, but for reference, it’s probably best to examine the categories that I am using first. The highest score in each category is 10, the lowest is 1.
Base pay - How much does this role get paid in base pay, on average, in comparison to the others? This is based on my experience as well as some research on Glassdoor and Payscale.
Bonus pay - How much incentive pay could this role earn?
Equity - People in startups get equity! How much do people in this role generally get?
Ease of entry - How easy is it to get into this role? A higher score means it is easier.
Opportunity to stand out - How easy is it to make an impact and get noticed in this role.
Control of performance - Do you actually have CONTROL over how well you do in this role? Or, is your performance at the whim of someone or something else. The higher the score, the less your success comes down to luck.
In the view below, you will see the roles stack ranked by their total score across all of these categories. Higher is better, lower is worse. The color of the bar corresponds to the score within that category, with a darker shade of blue indicating a higher score.
One other note: I am comparing roughly equivalent roles in terms of seniority. This is where a hard working, ambitious person could expect to land at a business to business technology company after 10-12 years of work in the role.
And as always, your mileage may vary. This is my opinion, although I have tried to ground my opinion in reality and hard numbers as much as possible.
These are the 10 worst IT jobs, counting down to the very worst
You can see the roles stack ranked above, but I want to go into more detail on all of these.
For each role, I will explain the ranking in more detail. What is the best part about this job? What is the worst part about this job? And, most importantly, what type of person would do well in this role.
I am counting down from the 10th worst to the WORST, so make sure to scroll to the bottom to see the worst role.
Also, and I cannot stress this enough, any job can be a good job with the right fit for the right person. If you happen to do one of these jobs and you love it, that’s great. But objectively, my ranking is attempting to zero in on the relative merits of each job, compared to others in tech.
The 10th worst job in tech - Sales - Director, Sales Enablement
What does this person do: The director of sales enablement runs the team that trains, informs, and arms the sales team with all of the resources and knowledge they need to be successful.
Best part about the role: Sales enablement is a highly visible role that lends itself well to team players. If you train and arm the team with what they need, they’ll love you.
Worst part about the role: Sales will never be satisfied with what sales enablement can provide. There will always be something else that is needed, so sales enablement is always at the mercy of expectations. The comp is also much worse than quota carrying sales roles.
People who would do well in this role: Team players who want to support others.
Do NOT pursue this role if: You want your effort to correspond to your pay or career advancement.
9th place - Support - Director, Professional Services
What does this person do: The director of professional services runs the team that provides paid consulting for customers. They oversee the consultants that work onsite with customers to run and integrate the product.
Best part about the role: Professional services can have interesting technical challenges that are fun to solve, similar to sales engineering.
Worst part about the role: Unfortunately, proserv is not a great place to get noticed. Because the work is offsite, it is difficult for people to see the impact. At some companies, you are also judged on your ability to bring in new business and that sets a weird incentive where you want the customer to need your help more than would be ideal.
People who would do well in this role: Ex-consultants will be very comfy in proserv since it’s essentially the same job.
Do NOT pursue this role if: You aren’t at least a little technical.
8th place - Support - Director, Customer Training
What does this person do: The director of customer training runs the team that trains customers on the product.
Best part about the role: Educating people and seeing them start to find success with the product can be massively rewarding. It isn’t too hard to get into, either.
Worst part about the role: Trainers are rarely seen and easily forgotten. What’s more, once you are in a training role it’s really hard to move out of. Bottom line: training is not a dynamic and noticeable part of company operations so it’s not a good place to be if you are ambitious. The money is pretty bad, as well (in comparison to other roles).
People who would do well in this role: People who get a thrill from helping people and educating them.
Do NOT pursue this role if: You are ambitious or want to make a lot of money.
7th place - Marketing - Director, Public Relations
What does this person do: The director of PR is responsible for making sure the company is written about as much as possible, in as positive a light as possible.
Best part about the role: PR can be pretty flashy; you get to work with external agencies and you often work hand in hand with senior management on interviews and other public facing activities.
Worst part about the role: More than any other role in marketing, someone in PR is at the mercy and whim of other people. Press doesn’t like your product? Tough luck. Data breach? Sucks to be you. And when you get GOOD press? Well… that’s expected! *pats you on the back condescendingly* PR is a tough gig.
People who would do well in this role: Outgoing, persuasive people that don’t want to be in sales.
Do NOT pursue this role if: You are uncomfortable being uncomfortable.
6th place - Operations - Director, Human Resources
What does this person do: The director of HR is responsible for recruiting people, and keeping them happy.
Best part about the role: HR is the ultimate people person job. If you want to take care of a team, there is immense capacity for deep meaning in this role.
Worst part about the role: HR is really challenging. Someone will always have a complaint. Recruiting will always be a little too slow and a little too low quality for people’s taste. Add to that the day to day sexual harassment and inevitable lawsuits and you begin to see the headache that this role can become. And if you manage to run everything perfectly? Congrats, you meet expectations. There is also very little room for advancement beyond this level, and the pay isn’t great in comparison to other roles.
People who would do well in this role: This is the team players team players job.
Do NOT pursue this role if: You don’t like people, or if you want to get paid a lot.
5th place - Sales - Director, Sales Operations
What does this person do: The director of sales ops keeps Salesforce clean and running smoothly, and makes sure the team gets paid accurately.
Best part about the role: The pay is ok.. If you are a detail person, it can be fun to figure everything out and set up infrastructure.
Worst part about the role: All day long, the sales team is entering bad data into Salesforce that you are responsible for fixing. While they are doing that, the management team is imagining new and increasingly complex ways to pay the team, which you have to actually administer. Even if you manage to keep up, where is the chance to outperform? How can you stand out? Where do you go after this role?
People who would do well in this role: Detail oriented people who will get meaning out of supporting the rest of the team.
Do NOT pursue this role if: You can’t keep 10 things in your mind at once.
4th place - Operations - Director, Accounting
What does this person do: The director of accounting runs the accounting team.
Best part about the role: Hmmm. The hours are a little better than in traditional accounting roles? Equity is also a nice plus that accountants don’t normally get, but that doesn’t make this role any more attractive in comparison to other tech roles.
Worst part about the role: You will probably get paid less than at a big accounting firm. This is also a pretty quiet corner of the tech world. You’re working in tech, but you’re not really a part of the action.
People who would do well in this role: Accountants who don’t want to work for a big company.
Do NOT pursue this role if: You are not already an accountant.
3rd place -Operations - Senior Attorney
What does this person do: Attorneys at tech companies generally work on contracts and MSA’s.
Best part about the role: Better hours than traditional legal jobs?
Worst part about the role: Holy shit, attorneys are used and abused at tech firms. You will be run into the ground with requests from sales, whose customers will spend every waking minute red-lining the shit out of your paper. You will spend the rest of your time cleaning up after the hasty signatures and rushed contracts that were done before you, or without your knowledge. For extra credit, deal with the HR lawsuits that inevitably will come up at a fast paced tech company with a bunch of young people who don’t know better (but should). Have any spare time after that? Go negotiate with some vendors!
People who would do well in this role: Attorneys who want slightly better hours than traditional roles.
Do NOT pursue this role if: Just don’t pursue this role, IMO.
2nd worst job in tech - Support - Director, Support
What does this person do: The director of support runs the support team. They deal with customer problems.
Best part about the role: I am drawing a blank here. It’s not toooo hard to get into? You get to help people who MIGHT then show you gratitude?
Worst part about the role: WHERE DO I START???? You will never be fast enough for customers. Or thorough enough. The sales team will be constantly hounding you to help THEIR customer first. The management team will always expect you to be improving your numbers as customer count increases, with no commensurate increase in headcount. You don’t get paid that much, in fact, support is often the LOWEST paid job in tech. Even if you knock it out of the park with all of those issues, you’ll get a nice “atta boy/girl” and that will be it. Awful.
People who would do well in this role: People who are gluttons for punishment. I mean, to be fair, if you REALLY like solving problems, then this could be ok.
Do NOT pursue this role if: If you are happy and want to stay that way.
THE WORST JOB IN TECH - Operations - Director, Security
What does this person do: The director of security is responsible for securing the data, customer information, and overall technical safety of the companies assets.
Best part about the role: You get paid? But… not that well considering the risk.
Worst part about the role: Everything. Absolutely everything. All day every day, people are trying to hack into your systems and get you fired. If, by some miracle you manage to escape the inevitable breach, you won’t get any recognition for it. What’s more, everyone in your company will be constantly sending you articles informing you of how hard your job is and how fucked you really are (they will always be assuming, of course, that you have no idea what you’re doing). And, if you DO get hacked, sayonara. Good luck finding another job, ever. This is absolutely the riskiest job in tech and the money isn’t anywhere near good enough to compensate for it.
People who would do well in this role: People who like to play Russian Roulette.
Do NOT pursue this role if: You are a human being.
Honestly, the jobs at the top of this list aren’t that bad, but I would aggressively avoid the bottom three. There are so many great jobs in tech, why take a bad one?