I’m Joining Automattic – Excitement Factor Bazillion

When I turned 42, I had a feeling that this year would be different for me. Actually, it was more than just a feeling, I had already started a process that has come to fruition.

I’ve had opportunities to interview at some of today’s most exciting companies

Starting on Monday, 19 February, I am joining Automattic as a Happiness Engineer. I’m beyond excited!

My journey, so far

I applied for the position in October last year. The position looked interesting, and it seemed like something I’d been doing to help out for years. Sure, it was different to any other position I’d worked in the past but it looked like a great opportunity to pursue.

Above all, it was an opportunity to join one of my dream companies.

I had my first assignment and interview about a month later. That was followed by another assignment, and a second interview shortly before my birthday. As you can imagine, that all went well because I received the best birthday present from someone outside my family: an offer to start a Trial.

A Trial is part of the interview process. It’s a paid opportunity to work at Automattic so both you and the company can get a good feel for you in the role. Automattic pays $25 an hour, which makes a huge difference. It gives you the space you need to really dive in and do the best you can.

I started thinking about the Trial like this: Automattic had given me an opportunity to work as a Happiness Engineer. I had almost the same level of access to just about everything that a full time Happiness Engineer had. I had the best possible chance I would have to prove to Automattic that I was worthy of keeping this new role.

Because I was freelancing, I decided to commit fully and set aside the four and a half weeks I’d need, and threw myself into it. I worked harder than I had for just about anything else in my working life, and I loved it.

It was challenging, there was a tremendous learning curve, and I had the opportunity to work with some of the most amazing people I’ve met. I was fortunate in that I could treat my Trial like a full-time job. I was part of a group of a dozen and a half people who didn’t all share the same luxury.

Not all of them made it through the Trial, for various reasons. All of them inspired me to keep improving, keep learning, and deliver more happiness with each interaction I had, whether that was with our users, or my fellow Automatticians.

My buddy, Rynaldo, and my Trial Lead, Daniel, gave me great feedback throughout my Trial. They guided me from the start and I owe some of my success to them. I also received so much help from other Automatticians who were doubtless incredibly busy, but who took the time to guide me to the answers I needed. Having the opportunity to work and learn from them is easily one of the best parts of working for Automattic.

There is so much more about the work that I love. It’s difficult to express it all. I spend my days learning, helping users with a wide variety of issues, improving my skills, gaining insights from people I admire … the list just goes on.

And then it became official

When I finished my Trial a week ago, and Daniel told me that the hiring team was recommending me to the HR team, I actually cried tears of joy. It was an incredible feeling.

This morning, I had my chat with an HR Wrangler and, before I knew it, I was official. I’ve been on a cloud for most of today, and I suspect this feeling is going to last a bit longer.

One of the first things you read when you start your Trial is “Welcome to the chaos”, followed by:

The only correct approach is to embrace the chaos, not fight it.

That pretty much covers how Automattic works (and it does, so incredibly well). We are a distributed team, working from all over the world in our homes, coffee shops, co-working spaces, camp sites, and more. We use Slack and internal blogs called P2s to communicate, share information, and keep connected.

Somehow the chaos doesn’t detract from just how effective everyone is.

I frequently found myself just amazed at how incredible everyone is at their jobs, and wondering whether I was worthy enough to join them.

My answer to my Imposter Syndrome was to ask myself this question: “Why not? I made it this far. Even if I don’t see it yet, the hiring team saw my potential and I owe it to them, and to myself, to realise that potential. So, why not me?”

As much as I achieved through hard work, and perseverence, I still believe I owe some of that success to the remarkable people who helped me along the way. They inspire me, they are my heroes, and I am grateful to them.

If you’d like to read a few more perspectives on working for Automattic, and their journeys, here are some of the stories that lit the way for me:

Oh, and by the way, we’re hiring! Join us. 😁


20 responses to “I’m Joining Automattic – Excitement Factor Bazillion”

  1. Shaun Trennery avatar

    Oh wow Paul. Congrats on the big move. Incredible company.

  2. The Other Sarah Marshall avatar


  3. The Other Sarah Marshall avatar

    MAN, I was READING those vacancy ads they post, for inspiration and some insight into their company (really cool ads, btw). HELL I am excited for you. THRILLED

  4. Paul Jacobson avatar

    Thank you, it’s an amazing opportunity.

  5. Carl Anderson avatar


    Carl Anderson


  6. Brett Deaton avatar


    1. Paul avatar

      Thank you very much.

  7. nuclearpengy avatar

    Super exciting; congratulations!

  8. Kevin O'Keefe avatar

    Big kudos to former attorney, @pauljacobson who is joining @photomatt’s @automattic. Incredible career path following passion.

  9. Leita avatar

    Congratulations, Paul. I’m so happy and excited for you!!

    1. Paul avatar

      Thank you very much Leita. 🙂

  10. kerawright avatar

    Congrats! This is one of the newer success stories and I notice that you didn’t have a Matt Chat. So that’s been changed? Also, do you have any insight to the application review process? Who looks at resumes?

    1. Paul avatar

      Hi Kera. As the company has grown, Matt simply didn’t have the time to have his famous Matt Chats with everyone. You can still request a chat with Matt, but the HR team has taken over that part of the interview process for the most part.

      As for the application process, the best way to find out more about it is to go through it. I suspect it’s a bit different for everyone who goes through the process, regardless of whether you are successful or not. I believe that the Hiring Team reviews resumes as part of their process.

      So, with that in mind, why not apply for a role that interests you and join us? 🙂

  11. No I’m not pregnant. Just been absent. For 6 months.
    For some reason I just stopped blogging. No great secret, no shocking reason. I just stopped. I also seem to have stopped using Twitter. Again, no idea why, no real reason. I just stopped.
    So, whats happened over the last 6 months?
    Paul has a new job. Its a pretty cool position in an awesome company that he gets to do from home.
    We got a dog! Her name is Nessi which means miracle in Hebrew. She is the cutest floof ever, even when she bites and nibbles to get your attention. I will write another post all about her soon.
    The morning after Nessi came to live with us.
    The kids have finished school and are well into summer vacation. In September, Aaron will be in 5th Grade and Faith will be in 3rd Grade. Where has the time gone?
    Our third Pesach in Israel. It was a good evening with my family and our friends.
    We all finally got our Israeli passports. This means we can travel easily throughout Europe. So give me your suggestions. Where should we visit?
    I dyed my hair. Purple and blue! I love it.

    Other than that, the last 6 months have been pretty quiet. Just the way I like it.
    Hopefully I will be back in the writing mood now and will post more often. Or not. No promises.

  12. Regina Foo avatar

    Congratulations, Paul! I love how you guys share your experiences in joining the big family of Automattic. They’re very inspiring and motivating! Hope to read more about your work as a Happiness Engineer and the stories on how you enjoy it!

  13. Paul avatar

    Today is a Big DayTM For Blogging, but probably only for me. Today is this blog’s 14th birthday! On 6 December 2004, I wrote my first post on this WordPress blog: In the beginning … Where this chapter all began … It was originally at a different domain, and has evolved over the last 14 … Continue reading My blog is 14 years old, today, and it’s a big day for blogging

  14. Paul avatar

    Another year has passed, and it’s my birthday again! 🎉 Quite a lot has changed in the last year. Last year, I looked back on 2017, and where my path had taken me. 42 I pretty much ended my retrospective with the following: While I don’t have all the answers (not even remotely), perhaps being … Continue reading 43 →

  15. Another year has flown by. We’ve had our ups and downs. Mostly ups though.

    Paul started a new job, we adopted a rescue dog, the kids are thriving.

    My Hebrew still sucks and we still don’t have a drivers license between us, but my resolutions for the new year are to sort those two things out.

    Every year here seems to be better than the last, so here is to a fantastic upcoming year!

  16. Paul avatar

    Chris Maiorana published a post highlighting why blogs remain relevant despite social media, perhaps because of social media.

  17. About me • Paul Jacobson avatar

    This Article was mentioned on pauljacobson.me

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