An Inside peek into a Remote Team Meetup

My favorite days of remote working aren’t the days when I get to work by a pool, or even when I get to stay home all day working on my couch in my favorite sweatpants (as a really strong introvert, that’s saying a whole lot there). My absolute favorite days are when I’m on a meetup and I get to see my coworkers in person, these amazing people here.

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2016 Automattic Grand Meetup

I posted a ton of pictures of last year’s Grand Meetup here and posted my thoughts here. And just realized that I forgot to post them for the Grand Meetup we had back in October of 2016 (which was around 5 months ago).

Wait, so what is a Grand Meetup?

Automattic is a remote company, which means that all employees work from wherever in the world they are. While we do have several offices or lounges in San Francisco, Maine, and Cape Town, no employees are expected to work out of there. The one time of a year we all get together is for the Grand Meetup (or what we fondly call the “The GM”) where Automattic flies all employees to one location where we all work together for a week.

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A Day in the Life of a Happiness Engineer

This post is part of a series describing what Automatticians do on a daily basis. You can read more posts like this by following the tag #a8cday on and Twitter.

Hi! I’m Tish, and I work as a Happiness Engineer at

I get asked a lot what it means to work from home, on a remote team where my coworkers live all over the world. So today I’m giving you an inside look into my day and schedule.

My days rarely look the same, because I love the variety. I’ve structured my Mondays to be my “long day” since I tend to get a lot of work done, so I work from 9am – 7pm.

This is what my Monday looks like:

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Lessons Learned from The Customer Survival Kit

Awhile back I was reading a book called The Customer Survival Kit. It was FANTASTIC! I highly recommend it. Several months ago I ended up writing an internal p2 post about it and sharing my favorite takeaways with my team at Automattic. But I was recently talking to a friend who also works in support and I wanted to share my favorite quotes from the book, so I decided to post an excerpt of my original p2 post here:

Angry customers. I’m kinda terrified of them.


Whenever I encounter an angry customer, it takes a lot out of me emotionally/mentally. And I wanted to find a way to get a better handle on those interactions.

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How I became a Happiness Engineer at Automattic Part 3: Paid Trial at Automattic

Part 1: Application Process
Part 2: The Interview Process
Part 3: Paid Trial at Automattic (this post)

What is a Trial?

This is the opportunity to work at Automattic, doing the job you’re applying for. It’s fantastic because you have the opportunity to see if you’d actually like the job and gives Automattic the opportunity to see how well you do the job.

It’s a paid Trial, so it really is a win-win situation. You get to try out the position, paid (this isn’t a salary but $25 hour), and see if you both think it’s a good fit.

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The schedule of a Happiness Engineer working in live chat

When I was first hired as Trial Happiness Engineer, I was  concerned about the flexibility of live chat.

I imagined a live chat operator being chained to their desk all day. But since this is Automattic the pioneers of remote working, how was this possible? How was it going to work?

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Women who WP Presentation: How to Rock WordPress

Yesterday I had the privilege of speaking at Women who WP, which is this wonderful meet up that gets together some amazing women and we have dinner and talk about WordPress, our stories, and what we’re learning.

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