I’ve been working at Automattic as a Happiness Engineer on WordPress.com for a little over two years now. The work is varied, and I love it. But the title ‘Happiness Engineer’ doesn’t really explain a lot about what I actually do.

I thought it would be good to share what a typical week might look like for me working as a Happiness Engineer.


I like Mondays. Being in the Asia Pacific region means that much of my day is still the weekend for many customers (and other people in the company). It’s usually a quieter day where I can catch up on loose ends and get ready for the week.

My alarm goes off. I snooze it once – but then I’m up. If I’m lucky there is leftover coffee from yesterday in the jug – and I’m not above warming it in the microwave.

This early in the morning I tend to work on the couch in the main living area – meaning I’m around if the kids happen to emerge from their sleep early.

The majority of my work is working directly with WordPress.com customers to help them with their sites. This morning that means a Live Chat shift where I’ll be chatting (in text form) with customers as they work on their site. From 6-8am I chat with a range of folks helping them with billing, technical challenges, CSS tweaks, and all sorts of other things.


At 8am my Chat Shift is over and anyone I was chatting to is now being assisted by one of my colleagues. I close my laptop and help my wife with the tail end of getting the kids fed/dressed/off-to school.

Most importantly – I’ll also brew a batch of filter coffee to last through the rest of the day.

Today I’ve got a slightly bigger gap than normal before my next shift so there’s time to head down to the harbour and go for a walk soaking in the sun and the sea breeze. One of the best things about working from home is how close I am to both practical locations (like school for the kids) and places like this…

From 10am-11am I have a shift working on tickets over email, before another hour of Live Chat. For today I’ve decided to work outside of home – so I head to my favorite cafe and spend those two hours working while enjoying coffee.

After that I head back home for lunch with my wife before some more work in the afternoon.

Another ticket shift. There’s a team of Happiness Engineers who share this responsibility of triage – we do it a few times a week. It involves taking an overview of all our incoming inquiries and doing things like removing spam, and making sure any duplicates are consolidated.

By 3pm I have wrapped up my triaging and am helping pre/school pickups and making sure the kids are home and settled. On some days I’ll be finished at this point depending on my shifts, but today…

My last chat shift for the day – I wrap up at 5:30pm and after a couple of follow-ups am done for the day.


No work today!

In order to make sure we can help people over the weekend(s) all Happiness Engineers work at least 2 weekend days a month. This week I’m working on Sunday – so today is my flex/day off.


After a week-day off, there’s always a fair bit to catch up on – so Wednesday is a busy day.

Today is a day full of chat shifts – in that sense, it is much the same as any other. I still have shifts broken up so I can help with School pickup/dropoff. For today I work at home in my office – where I favor a standing desk.

Let’s be honest – it’s not normally this clean

A few notable things that happen through the day:

  • I spend some of my time liaising with our Product teams to make sure we know what future changes and improvements are coming, as well as helping the whole team of Happiness Engineers provide feedback that we get from working directly with customers.
  • While chatting with customers – I’m also involved in Slack channels (our internal chat tool) – chatting with my immediate team-mates, helping out other Happiness Engineers with questions, and chiming in on conversations.


This week is a bit special. I’m starting to ‘Buddy’ one of our potential new Happiness Engineers who is doing a trial period. Everyone who ends up as a Happiness Engineer goes through a paid-trial to see if they are a good fit. Today is training day!

Rather than my normal chat or ticket shifts – today I work 1:1 with the new trial Happiness Engineer: walking them through the way we do things; helping them help their first customers; and getting used to the way we work. It’s a really great experience.


Friday is a pretty regular day – helping customers over chat and email. I also start drafting a blog post (to be posted internally) to help demystify some of the confusion around SSL certificates and how they work.

I usually spend time on Friday closing the loop on conversations, finishing up any project work, and reading posts I have sitting open in tabs in my browser.


Today is my weekend day. These days are usually a little busier in chat (as we have less Happiness Engineers around) but it makes for pleasantly paced day. Even though it is the weekend – I still tend to try and have an early shift.

With my morning shift finished – I have a break to spend with the family.

After a break of a few hours – I have more chat shifts spread through the afternoon, along with tickets. And then I’m all done for the week 🙂

Sound like an interesting way to work? We’re hiring Happiness Engineers at the moment and would love to have you join us.

Published by jordesign

I'm a web guy who lives in Wollongong, Australia with my awesome wife and 2 little girls.

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