5 Lessons I’ve Learned From One Year at Automattic

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As of a few days ago, I’ve now been working for Automattic, makers of WordPress.com, for just over a year. It’s hard to believe that just a short time ago, I was ending my trial and starting full-time on a product that I both love and believe in.

I’ve written quite a bit about the trial process and what a day in the life of a Happiness Engineer looks like. But, I haven’t written much about insights working for a distributed company or how I now view customer support. In other words, what I’ve learned over the past year working at Automattic. In no particular order, here are the top five items.

WordPress.com is extremely powerful.

There’s a pretty common misconception that in order to build a truly huge and powerful site, you need to move from WordPress.com to a self-hosted install. The self-hosted version of WordPress is incredibly powerful, and yes, it does offer some features like installing your own themes or the use of plugins that WordPress.com doesn’t.

I would argue that those elements are largely overrated in the grand scheme of starting a blog. I’ll be writing a post about this in the future, but I think WordPress.com is the better choice for many bloggers and writers.

Takeaway: WordPress.com is more powerful than I ever thought.

Productivity should never be based on time.

I’m fortunate to make my own schedule and work from home, two luxuries I never had prior to working at Automattic. The initial downside was this feeling of needing to overcompensate by working more hours. Since my coworkers weren’t seeing me around the office each day, I felt like I had to make an effort to be online more to show how much I was getting done.

In some distributed environments, this might be the case. Employees might need to hang out longer online to show their face. I’m fortunate that at Automattic, performance is based on outcome, not hours put in.

Organizations should be built on a foundation of trust, particularly organizations that want to work in a distributed fashion. At the end of the day, it comes back to hiring great people and letting them work in the way that makes them productive.

Takeaway: Your measure of productivity should be based on output, not time commitment.

Yes, you can take time away from the computer. In fact, you should.

I’m a chronic worker. I love being busy and secretly despise taking time off. When I’m away from work, I feel like I’m missing out on everything. When you combine this kind of mindset with remote work, where logging on is always a possibility, you can have a recipe for disaster.

At the start, I was tempted to constantly be available for pings (messages on Slack), notifications (mentions on our internal blogs), and emails (in case something slipped through the cracks).

Now, I’m exactly the opposite.

I don’t have email on my phone (something I would recommend to everyone). I don’t have Slack on my phone (unless we’re at a meetup, and I need to communicate). I still have the WordPress app on my phone so I can create posts, but I have notifications turned off.

Guess what? The ship still runs smoothly when I’m offline.

Not only do I enjoy my time away from work more, it helps to recharge me for when I actually do come back to work the next day/week/whenever.

Takeaway: Learn to take time off and enjoy it. For many, that’s a skill that needs to be practiced.

If you have an opinion, you should voice it.

When I was on my trial at Automattic, I was afraid to jump into big conversations that were happening on our internal blogs. The conversations were available for everyone to see so I was worried that I would look silly or stupid. After all, most of the people had been there far longer than I had.

Now, when I lead training sessions for new hires, I make sure I tell them to jump into conversations and provide feedback if they have something meaningful to say. If you’re hired on at Automattic, it means that the company values your opinion. If you have something valuable to add to the conversation that will improve the end experience for our users, we want to hear it.

Voicing your opinion can feel a bit like standing naked in the middle of a party. You’re expressing your thoughts and emotions for everyone to potentially laugh at. But, a company environment where everyone is scared to speak up is certainly going to experience a lack of innovation. Improvements come out of a discussion amongst many, not the sole direction of one individual.

Takeaway: Don’t be afraid to express your opinion.

Give customer support the freedom to solve problems.

I recently had an issue with an Amazon order, and I contacted customer service via live chat to get some help. The product I ordered (a Jawbone UP24) came without a charger, rendering it completely useless. I was happy to buy another band at full price, but I didn’t want to be out two amounts (one for the original purchase and another for the new purchase). I was asking for a credit of the original purchase on my account that I could then apply towards the new purchase while I return the old item. The agent then explained that she was just a regular customer service rep and was only authorized to credit up to $5.

Prior to Automattic, I had never worked in a role strictly devoted to customer support so my knowledge of the role elsewhere was and is still pretty limited. At Automattic, Happiness Engineers have the capability to do whatever they feel is necessary to assuage a user. This extends to refunds, credits, free upgrades, etc.

The environment at Automattic might not be possible to duplicate when you have hundreds of thousands of employees helping to serve customers. But, then again, perhaps it could be.

If you focus on hiring the right people, perhaps you can give hundreds of thousands of customer support reps the autonomy to do whatever they feel necessary to keep customers happy. In my personal experience, handicapping customer support staff only creates a worse user experience overall.

Takeaway: Hire the right people and give them the autonomy/resources necessary to do great work.


I put the slug as automattic-anniversary-one on purpose. I’m excited to learn and grow at Automattic for many more years to come. Here’s to many more lessons in the future!

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