Five standout skills to be a successful Happiness Engineer

Happiness Engineers love helping people use Automattic’s products like, WooCommerce, Jetpack, and more. While the desire to help others is important, Happiness Engineers must have other skills to successfully help customers in live chat and by email. With that in mind, here are my recommendations for those wanting to improve their skills as new or aspiring Happiness Engineers. These tips are from my personal experience working as a Happiness Engineer for more than seven years.

Love of Learning

The WooCommerce ecosystem is so vast that nobody can possibly know everything. And while we have a lot of smart people working here at Automattic, occasionally no one knows the answer to your particular question! So how do you handle that? You have to learn. And, if you don’t enjoy constantly learning, you won’t enjoy being a Happiness Engineer.

Sometimes that learning process takes place over months. Seeing multiple support requests about a complex extension forces you to do some in-depth research and really learn the plugin inside and out. Other times, like during live chat shifts for example, you need to learn quite quickly. So quickly, in fact, that it seems to the customer that you knew the answer right off the top of your head!

Reducing Complexity

Having worked in support roles for over 10 years now, one thing stands out to me as an absolutely critical skill for all support workers to have: the ability to take a complex concept and distill it down into something simpler, something that non-technical folks can understand.

Similar to how Automattic’s company goal is to democratize publishing, our goal in the WooCommerce division is to democratize commerce. In order to do that, starting an online store cannot be some unattainable goal to the average business owner. It’s our job as Happiness Engineers to help them accomplish something that at first may have seemed far too technical for them. Part of that is knowing how to simplify things in the right way.

Reading and Writing

As a remote company from the very beginning, Automattic is built on a foundation of written communication. Whether it be in our massive Slack instance, or spread across our hundreds of internal P2s (, the written word is critical to our day-to-day work. As a Happiness Engineer, just as in any other role at Automattic, you’re going to be doing a large amount of reading on a daily basis to keep up with internal news, events, best practices, and so on.

Writing is, of course, just as important. Most of your writing as a Happiness Engineer will be customer-facing, i.e. in emails or live chats with our users. However, it’s still important to be able to transition between different styles quickly. For example, live chat support is suited to shorter responses and a more conversational tone. But in the next moment you may need to write a lengthy and technically detailed bug report on GitHub. The ability to adjust your communication style for each “audience” is a necessary skill here.


The most important responsibility we have as WooCommerce Happiness Engineers is to our customers. We’re here to help them overcome challenges and grow their business. How this happens, though, is always subject to change. That’s why it’s important to keep in mind that, as a Happiness Engineer, your workday will very often be more than just responding to customer questions.

We have small teams (referred to internally as “guilds”) that handle a wide variety of projects, such as updating our documentation to reflect the latest changes in plugins, scheduling shifts for others so that our support coverage is fully staffed when needed.

Investigative Mindset

Being a Happiness Engineer sometimes feels a lot like being a detective in a crime thriller. Initially the situation is not very clear, but over time, by asking the right questions and digging for answers, you can piece things together, little by little. The reward comes when you finally discover the critical bit of information that solves the puzzle, and then all the pieces that came before fall into place, and you can understand the whole thing at once.

Like a detective, you need somewhat of an investigative mindset to succeed as a WooCommerce Happiness Engineer. We have an old saying here that sums this up:

Intuition + Investigation > Memorization

It means that knowing where or how to find the solution to any given problem, plus a bit of intuition that comes with experience, is better than memorizing a rigid set of steps for solving it. This is because, over time, the right way to do a given thing will change. This tidbit of wisdom still serves me well after 7+ years.

Are you interested in working in customer support for a distributed company? You can read more about the Happiness Engineer role and find instructions for applying here.

2 thoughts on “Five standout skills to be a successful Happiness Engineer

  1. You had me at writing. Besides bug reports on GitHub would you say it would be good to give a non-brief very detailed response over emails . You did mention that live chats require brief straight to the point response does that go for email tickets as well or it depends. I would love to become a Happiness Engineering some day.


    1. The answer is of course “it depends.” 🙂 Everyone we communicate with in support is at a different point in their WordPress and WooCommerce journey. Some folks are just starting out with their first store, and they might benefit from longer, detailed explanations. Others might already know WooCommerce inside and out, and they just need a quick verification from us on how a certain bit of our code works. In those cases, we can get right to the point.

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