The Ultimate Happiness Engineer Starter Pack

So you just found out that Happiness Engineering is an actual job. You always thought customer support is all about scary call centers, but then you met some folks who do this and have fun. You might have heard some stories that sounded too good to be true, and then became jealous when they turned out to be quite true indeed.
Maybe you’d never heard of Automattic before, and only had a vague idea of what WordPress is, but the more you learned about what Happiness Engineers do, the more you realised this is the job you always dreamed of.
Does that sound anything like you? That’s great, you’re most probably a my kind of person. Here is the ultimate guide that will answer the questions you have on your mind, and help you get started as a Happiness Engineer.

How do I know this is the job for me?

Not everyone can be a Happiness Engineer. Not everyone would even want to be one. If all the jobs you had so far somehow revolved around people and problem solvingthis is a good sign. Here are a few other ones:

  • You enjoy working with people. This is an absolute must. Happiness Engineers work mostly with people, even if they only “see” them online. If you’d rather hide in your cave and do stuff on your own, consider a different position out of the many we have.
  • You have high empathy levels. You care about people and do your best to help them. It’s easy for you to imagine how others perceive the world, and how it’s like not to know something.
  • You love solving puzzles, learning new things, and have exceptional googling skills,
  • Your secret superpower is explaining technical stuff in terms understandable to your mum or seven year old kid,
  • You’re willing to stretch yourself for 4 weeks and get baptised in fire during the trial. There will be more on that later.
You probably noticed there’s no mention of technical skills on that list. I skipped that part on purpose. The only technical skill you really need is the ability to google and learn new technical skills, fast. Our products evolve over time, so get used to learning by trial and error rather than by heart.
Before you apply, it’s good to have a decent understanding of HTML, CSS, domains, HTTP requests, and browser debugging tools. It’s even better to know how WordPress works, and how different people use it. Coding skills are not required by any means, but often help. However, if you know how to google and how to learn, you should be able to prepare yourself for the trial in a few months, even if you don’t know anything about WordPress or HTTP yet.

How do I learn about WordPress then?

Glad that you asked! The fastest way to learn is to start actually using it. There’s a few things you can do, and the first one is obviously to…

Start a free blog on

This is the product you’ll mostly work with during your trial. The free version doesn’t have all the awesome features of premium plans, but it’s more than enough for a first encounter with WordPress.
Challenge yourself to use the product, so you can learn how it works. Play around with the site design and see how it looks with different themes. Connect it to your Facebook and Twitter accounts and observe how your posts get automatically shared with the public. Set up a homepage, some widgets, and a contact form.
Commit to adding at least one or two posts per week. If you don’t know what to write about, post photos of your food, dog, or kid. Or if you’re like me, find a rainbow pencil, ask people to draw something for you, then post it on the blog. I’ll be happy to ship a rainbow pencil wherever you live, if you need one.
Your blog doesn’t need to be professional or serious, as long as you’re consistent and learning this way
Still doesn’t sound like fun? If you’re too pragmatic to play around with no purpose, you should probably try something else…

Find a non-profit without a website, and help them create one

You’ll learn much more this way, as their needs might be specific and unusual. It may turn out that the free plan is not enough, and you will need to move to a self-hosted WordPress and install all the themes and plugins yourself. Perhaps you’ll even end up setting a fundraising campaign for them, or an online store of some kind.
Above all else, working for a non-profit you will learn how non-technical customers communicate what they need, which will be invaluable at your work. You’ll also have a great story to share in your application letter. Plus you will earn karma points. That’s a quadruple win.
Not sure where to find an organisation you care enough about? Start with the Worldwide NGO Directory, or find a local one. In the NGO catalog provided by the city of Warsaw, only half of the entries have a website link.

Start helping out on the forums

And start it sooner than later. There’s only so many ways to break a website you can come up with yourself. Other folks in the forums will surely have other ideas, and helping them will speed up your learning a lot.
You’ll spend the most of your trial on, so start on the support forum. Reply whenever you know the answer, and follow up if there’s extra questions. Observe what others say in threads where you don’t know what to do, watching out especially for staff answers. These people got the job, so they might have an idea what they’re doing.
This shouldn’t take more than few hours per week – you probably still have a full-time job at this point, so the worst thing you can do is to burn out before even applying. If you don’t have any coding background, and still have some free time, you can learn a bit about CSS or troubleshooting with Chrome Dev Tools.
Once you’re comfortable replying to about 80% of the forum threads you open, you are ready to apply. Provided, of course, that after a few weeks of blogging, setting up websites and helping folks out in the forums, you still think it’s super fun and would like to keep doing this thing.


Before you apply, make sure to present yourself in the best way possible. So as the first step…

Spice up that resume and application letter

It’s too easy to spot a generic application sent to a hundred companies for a hundred different positions. Yours will be a very specific one that shows why you’re a good fit for a Happiness Engineer. No matter what your past job experiences were, they are always relevant, as long as they helped you learn how to solve problems, communicate with people, or act in difficult situations. Make sure to present them in this light.
There’s more than just past jobs you can write about in your application. Write why of all companies on the planet you want to work for Automattic (because you do want to work here, right?). Write what you liked most about blogging, setting up websites and helping out in the forums, and what you learned in the process. Write how and why you’d like to make the world a better place.
There’s no need to write a long application letter, a few short paragraphs are surely enough. It’s much more important what is in there, so make sure to check suggestions on the job listing page, and reference at least two of them. Double check for any typos and ask a friend to triple check. Ready? Then send that email and…


It may take a few weeks before you hear back. It’s a little bit stressful, but perfectly normal. Use that time to expand your knowledge about WordPress and keep replying in the forums. If you make it to the trial, domain-related questions will make a big part of your work, so make sure to review the All About Domains page.
Or if you want to learn the fast way, buy a plan, move your site and existing domain there, and immediately lose access to the email you used to send your resume. Bonus points if that’s also the email on your account, which now controls all the settings of the domain you moved. You’ll learn much more in one day than you would if you just kept reading articles for a whole month. Believe me, I’ll never forget how nameservers and MX records work.
Now is also a good time to start reading the Customer Service Survival Kit. If you only have time to read one book during these few months, make it this one. You’ll thank me for this later, and will be wondering where this book has been for your whole life. If you absolutely don’t even have a spare while to read it, here are the key lessons I’ve taken from it.

Interview time!

All interviews at Automattic are in Slack, just like the most of internal communication. If you’re used to traditional face to face interviews, this may feel very weird at first.
Don’t be surprised if the questions will be different from what you’re normally used to – since you can use Google during the interview (and, khem, during your everyday work), traditional knowledge quizzes don’t make much sense here.
Also, once you’re finally hired, we’d love to hear what is your spirit animal, what you were like as a child, and what box of cereal you would be, but a first interview is probably not the best place for these.
If all goes well, you’ll be invited over to the next step of the process, which is…

The Homework

You’ll get a few problems to solve – either to write down an answer, or to set up something on a WordPress site. You can take as much time as you need to complete it.
If you’re not sure what to do at any of the steps, remember that “I will not just work on things that are assigned to me” is part of Automattic creed. Whenever in doubt, feel free to go above and beyond (and don’t forget to google!).

Second interview

For me, this one was mostly about the homework. There may be more technical questions at this point, but if you did all the assignments yourself, you should have no problems answering those.
If you successfully pass the second interview, you’ll be invited to where the real fun begins.

The Trial Process

This exquisite goat is brought to you by Michael Kahl, to help you relax a bit before the rest of your journey
The idea is very simple – you get hired as a test, both for you to see if this is how you want to spend a large portion of your life, and for the company to see if you’re doing a good job. The details have changed a lot since I was on my trial, but you can expect working 25-30h per week for up to several weeks. You will get paid for each hour you worked.
For the first week you’ll start out in the forums (yes, the same forums you should be already familiar with), along with a bunch of other candidates. If you do a good job there, you’ll take a quick training on internal workflows and tools and move over to working on live chat and tickets. Get ready, this will be intense.
You’ll need to learn a ton of things during the trial, and you’ll need to learn all of them fast. The most important one is how to search for answers – we have a vast library of internal and public docs, which soon will become your best friends.
You’ll also get a buddy – another fellow Happiness Engineer who will help you with rest of your trial process. You can always ask anyone for help (and are strongly encouraged to do so!), but if you feel that your questions are too silly, or you messed something up, your buddy will be the best person to help you get yourself out of trouble.

Can I do the trial while working full-time?

Yes, it’s doable. Tough and exhausting, but doable. I did this, my friends did this, I don’t have official stats but it’s likely that the most of the company did their trial while still working full time, or taking care of small kids (but very few people did both!). It helps if you prioritise sleep above everything else, give up on most household chores, and have an understanding and supportive partner.
Still, despite having the best partner in the world and giving up on pretty much everything except for work, I was physically and mentally exhausted by the end of my trial. The process is so intense, and you learn so much over such a short time, that it would be tiring even as the only job you have. Doing it as a second job is certainly going to stretch you out.
Luckily, it’s easier to stretch yourself when you know where the finish line is. No one would be able to work this way in the long term, but a few weeks’ sprint won’t do that much harm.
You’ll also learn things about yourself you always deemed impossible. Like that you’re able to wake up daily at 5:30am, to do some live chat in the morning before going to work. I still have no idea how I did this. There’s no such hour as 5:30am on any of my clocks.

What is evaluated on the trial?

Everything! How many interactions you can normally do in certain time, and how accurate your answers are. The way you speak to customers, especially if they are angry, confused or upset. The way you ask for help, the way you help others, the way you give and receive feedback.
If that sounds scary, imagine how scary it must be to be hired based on what your spirit animal is… Here you are given a fair shot to do the work, and prove yourself competent.

Final Interview

This one is to see how you fit in the company culture. What makes Automattic such an awesome bunch to work with, is that everyone cares about what they’re doing, and agrees on the values written down in the Creed. If you’ve reached this stage, there’s high chance that you do fit here, so this one will likely be a friendly chat.

What if I don’t get hired the first time?

You’re more than welcome to apply again in a few months. Many of our colleagues were hired on their second try. Get some rest, learn some more, read more books on customer support, and come back refreshed whenever you feel that you’re ready.

Is it worth all the hassle?

I may be biased, but it totally is! Yes, the hiring process at Automattic is much longer and complicated than in most companies. From the moment you send your resume, till the moment you start working full time, it might take about 3 to 4 months, or even more.

Still, because of the very fact that the process is so long and complex, only people who do care about working here end up working here. Coincidentally, these people also tend to care about their colleagues, the products they create, their clients, and a whole lot of other things. And, believe me, I know how big of a difference it makes.

10 responses to “The Ultimate Happiness Engineer Starter Pack”

  1. Reblogged this on Luminus Alabi and commented:

    If you were wondering what a Happiness Engineer is or does, what a hypothetical day in the life might look like and how to get to work for the company behind, and other amazing products, my colleague who’s also an awesome teammate has provided the ultimate starter pack here.

    Don’t say I never did anything for you.

  2. Hi, I just found your site and wanted to say thank you!!! I am looking to apply as a happiness engineer and am excited and scared at the same time..your post helped me better understand what is needed. I excel at customer service and love to learn so but I am still a little rusty with the technical knowledge, but as I said before your blog pushed me over the edge to apply and have fun doing it!!! Thank you!!

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