I get about a half-dozen emails a year via my contact form asking me this question or asking related questions, like how to craft a resume, or what it’s like to work at Automattic. I thought I’d jot something down so I can just send a link the next time this happens, as my advice hasn’t changed much over time. :)

I’ve been here for seven years as of this writing, so I thought I’d share what I tell people who ask me this question (in a slightly expanded format). I’m not involved in hiring. This is not “official” advice of any kind. It’s just what I say to people, made public and repeatable.

First things first:

I love working at Automattic. You might not.

I will extol the virtues of my job whenever you ask me about it. It’s the best place I’ve worked, and I have found it to be very rewarding.

Not everyone will feel this way. The amount of freedom we have to get or not get our jobs done is unlike anything else out there. It can be very isolating and lonely to not see your team in person more than two to three times per year. I think even those of us who have embraced what we do struggle with this from time to time, and for some it can be significant.

But if you are willing to engage without having to be asked to do so, love working with people who are intelligent and come from all walks of life, and are down with being challenged often, you’ll probably fit in well.

So, how to get a job here? Let’s talk.

Read through our open positions and see if something is right for you.

You can find Automattic’s open positions here. Take a look and see if you spot something you’d enjoy doing and think you can do well. Read the job description and requirements to make sure you understand them and know how you would theoretically fit in the role.

Now, take a strong, focused look at the part of the job listing that talks about how to apply. This is going to be very important. :)

Follow the instructions regarding how to apply. Read them twice.

There are some things you will see in every job listing regarding how to apply. Take note of them and follow them. They are not there at random. Basically:

  • Make a resume/CV/whatever you want to call it. Prioritize and emphasize experience and skills that would directly impact the job role, but don’t ignore even side things that make you unique.
  • Attach it to an email sent to the address provided in the job description. The email is your cover letter. Introduce yourself. Be concise. This is your first impression, and it’s text-only. (As we are largely a text-communication-driven company, you should get used to this idea.) Make sure you include anything that’s specifically requested in the job description call for applications.
  • Double-check your spelling and grammar. Fix anything you need to fix.
  • Check it again.
  • Once more.
  • Send and wait. :)

You might get a trial; you might not. But putting yourself out there is the first step.

(Oh, and if you don’t know about how our hiring works with the trial process, where you perform contract work to see how that goes, you should probably read about that.)

I’m not lying when I say that’s pretty much it. When you boil down the process of applying for a job here, it’s pretty simple. That said:

Here are some focuses/traits I believe in based on my time at Automattic.

Again, let me stress this is my opinion and not in any way “official.” Nothing I say here is even remotely a guarantee, and I don’t have anything to do with hiring (really, I don’t), but these are things I will usually recommend to someone when they ask me personally what they can focus on.

These are mostly things I really like to see or admire in people I work with. :)

Be open to criticism.

It’s totally possible you’ll be rejected for the job, either before or during the trial process. When this happens, you may receive some reasons why you were turned down. Or you’ll receive some constructive feedback during your trial. Be open to it. Embrace the idea that you don’t know everything, because believe me—as a full-time employee for many years now, I still realize this often.

Be dogged in adapting to and implementing that criticism.

I applied to Automattic three separate times over a year-and-a-half before I received a trial. I had to change focus mid-trial before I was hired based on feedback. Some of the best colleagues I have at Automattic went through a trial, received feedback and a rejection, and then trialed again later with success. If and when you receive feedback, take it to heart and then apply it. Or apply again. Or both. :)

Be willing to say up-front when you don’t know something and be open to learning.

I would rather work a million times over with someone who is willing to admit when they don’t know something or are stuck on something and ask for help than someone who tries to fake it. Admitting you need help is not a weakness. It is literally impossible for everyone to be an expert at everything.

Be willing to help others.

I’m big on leading by example. Everyone has gifts and strengths, and everyone is at a different level. Just as you should be willing to let others help you, be willing to share your knowledge and experience with others. Be kind and instructive. Don’t always offer to just take charge of things—though on occasion, that’s necessary—but aim to level up your (potential) team.

Be yourself.

Automattic contains the most diverse and interesting group of people alongside whom I have ever worked. It is an amazing collection of individuals from whom I have learned much and with whom I have enjoyed spending time during meetups. Embrace this and be willing to commit yourself to it as well. (BTW, if the real you is introverted, that’s totally OK. There are lots of us here. If you have to take a break, we understand.)

Have at least a passing familiarity with the Automattic suite of products.

How much of this depends greatly on the job for which you are applying. Some positions might not require a lot of PHP or familiarity with WordPress. Others will be based almost entirely around this. I think it’s a good rule of thumb to at least know the core business of Automattic and what we do before wanting to work here. :)

Embrace open source.

An open source ethos drives Automattic and is core to our identity. Know what that means. Past and ongoing contributions to open source projects, whether it’s code, testing, design, documentation, or whatever, will give you valuable experience in what it’s like to work with those types of projects and is a bonus.

(Again, this will somewhat depend on your desired job role.)

Get comfortable with text-only communication. And in learning how your writing tone can be interpreted.

To be honest, I still have trouble with this sometimes. Text communication is hard. Without vocal inflections, facial expressions, and other body language, it’s easy to read something and get the wrong impression.

It’s a skill to craft your text communication in a way that others will understand your tone and intention. Dedicate yourself to learning that skill. (Yes; sometimes this means using emoji. They are very, very helpful for establishing tone.)

This space reserved.

I’m sure there are things I’m not thinking of, but I have been writing this blog post for three days and I should probably just publish it. If you are a fellow Automattician and reading this, and I forgot something obvious, ping me and let me know. If you are a reader and you have additional questions, feel free to contact me. I’ll edit some things in to this post later if needed.

I will never stop learning. I won’t just work on things that are assigned to me. I know there’s no such thing as a status quo. I will build our business sustainably through passionate and loyal customers. I will never pass up an opportunity to help out a colleague, and I’ll remember the days before I knew everything. I am more motivated by impact than money, and I know that Open Source is one of the most powerful ideas of our generation. I will communicate as much as possible, because it’s the oxygen of a distributed company. I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.

If you have talked with me, my skepticism with regards to Avyd and what they are doing should not be much of a surprise at this point. (I hesitate to talk about it much because there are good people I respect who are doing business at and with Avyd and I am of course always worried about causing hurt.)

I need to say something about this, though.

Today, they are talking about the support they’ll offer as part of their service:

This reminded me of the job posting they’d put up a couple of weeks ago, about which I’d intended to say something more directly.

The listing is here, but I’m assuming that it will expire at some point, so I’ll put the pertinent bits below:


  • Customer Service Representatives are responsible for handling our Client’s highest level of service issues to ensure customer issues are resolved in an efficient and timely manner. Agents provide knowledge and expertise to all online customers to effectively resolve any service-related, while balancing both the needs of the customer and the business.
  • Use empathy with the customer; allow them to vent frustrations, while staying in control of the conversation and maintaining focus.
  • Must be able to multi task
  • Follow up with customers to ensure issue has been resolved
  • Will be answering customer support tickets, inbound calls, and support chats.

Successful Candidates will have:

  • Previous Customer Service experience
  • Proficient in typing and computer skills
  • Energetic and motivated personality
  • Gaming knowledge
  • Available to work nights and weekends as needed
  • Be fluent in English
  • Team player
  • High School Diploma or equivalent

What We Offer:

  • Unparalleled work environment
  • Unlimited growth from within
  • Paid training
  • Continued development beyond entry level
  • Travel opportunities
  • Career advancement into management

On its own, that’s mostly fine. It’s a lot of attention-splitting, and the bit about nights and weekends without specifically stating what that means is a little concerning.

And then you get to the stuff about “growth” from the support position. It’s so much of a focus that it’s literally half of the bullet points in the list of “What We Offer.” It’s a red flag, especially when you hit this part:

Job Type: Part-time

Salary: $10.00 /hour

I don’t suppose I need to state that this is in an office and not remote, because the job posting should lead you in that direction on its own.

This is troubling because it doesn’t see support as a worthwhile career in and of itself. I am growing to understand that my current employer is somewhat unique in this, but I want to see the idea and the respect for support professionals continue to grow.

User support has been my full-time, salaried and benefited career for the last six years. It supports my entire household. I have had different responsibilities and been on different teams, but through the whole thing, I have been well-appreciated and been given the ability to build my career on having pride in the fact that I make our customers’ and clients’ lives easier, and that the ability to do so in an exceptional way is deserving of being a full-time employee.

The wage and (lack of) benefits in this Avyd job posting is sadly reflective of how a lot of tech sees support. Support is a place where you go to wage slave until you earn yourself a place as a supervisor, when you make a bit more and maybe get full-time, and then after even more time you might end up in charge of support for something and possibly get a salary and benefits. Or you have the (often just a) pipe dream of learning another skill and changing job responsibilities, which is seen as a promotion simply because you aren’t doing support.

I’m proud to work somewhere that prides itself on seeing professional support as a career, helping people build that career by supporting them and helping them develop, and giving those people good compensation, good opportunities, and good resources with which they can make the services we provide amazing experiences for the customers who pay for them. We make all employees who don’t work in support do a rotation in support every year, and every new hire regardless of position does front-line support for the first three weeks.

User support and respect for the people who work it is foundational to the culture here, and I wouldn’t have it any other way. No matter your industry, I encourage you to consider making it just as important to your company as well.

And yes; we are hiring.

I had meant to write this much earlier in the day, but it’s been so busy that I’m just now sitting down to hammer it out.

Today was the sixth anniversary of my start date at Automattic. It’s hard for me to think that so much time has gone by and to consider all the things I have learned, accomplished, and even gracefully failed at (and learned from!) as an Automattician.

At six years, that means I’ve been around longer than a huge part of the company as it stands now. From the time I joined to now, the company is now almost 10x the size, which I could not have imagined when I started. And we keep finding amazing people to work with, who we can hire because we don’t make them move anywhere. :)

I’m constantly grateful for the opportunity I have to work with colleagues who are as thoughful, intelligent, patient, kind, and supportive as my friends at Automattic. And I get to work with an open source ethos and a dedication to improving the ability for people everywhere to have a voice. It’s humbling and sometimes even intimidating.

Think about all the things in my life I likely would not have had I not been doing this for the last six years:

  • Learn so much more about code and about how things just work, even though IMO I still have so much more to go and am nowhere near where I want to be
  • Gain the ability to leave a job and path I ultimately found much less fulfilling and satisfying to work and learn from and alongside fantastic people
  • And do it while now getting to spend more time with my wife and children than I could have otherwise, simply by eliminating my commute
  • Travel to places I never thought I’d see or experience
  • Help countless people with their WordPress sites so they can get on with making content and not worry about the technical bits
  • Be constantly challenged by new problems and questions that push me to my limits and nudge me to develop new skills and proficiencies
  • Help coordinate the migration of an entire platform (Live Spaces!) of sites over to WordPress.com
  • Launch some of the biggest websites on the planet with some of the coolest partners around
  • Re-discover my love of Doctor Who
  • Learn there are other smart people out there who think pro wrestling is rad
  • Overall, worry a lot less and just have fun with what I do, how I balance that with the rest of my life, and who I am

There are probably other things I am forgetting, but I have only five minutes left to publish this post. :)

I really do love what I do. Maybe you’d like to join me? We’re hiring.

At WordPress.com VIP, we are currently hard at work designing new platform services for our clients we think will help us take their sites to the next level of WordPress awesome. And today, my colleagues open sourced two of the tools we are using internally.

(Both of them are use on this very site, actually—because my blog has been running on our new platform as a test for some time now.)

The first is VIP Jetpack, which is a series of forced module activations and testing preparation we use with the Jetpack plugin suite for VIP Go. (Yes, this site and other sites on VIP Go always use Jetpack. No, it’s not a performance hog.)

The second is VIP Support, which we use to access client administration pages when troubleshooting a site. This ensures that we don’t always have admin access to client sites, but that we can assist when something goes wrong.

This project is so exciting for me, because we have a dedication to developing as much as we can in the open, a test-driven development process, and a peer review-heavy culture. I’m not actually generating any of the code you see in these repos, but that doesn’t mean I’m not proud of what we are accomplishing and how we are doing it.

By the way, the source used to power this site on that same platform is available here; I’m working on things in the open as well even though I don’t have much time to work on them. :)

Andy Skelton, one of my colleagues at Automattic, also recently returned from his sabbatical and wrote a quick post about what it was like to come back. I echo this thought in specific:

Automattic can change a lot in just three months. People come and go, projects advance, priorities evolve. Three things are making the reintegration easy: full documentation, good search and great coworkers. It’s good to be back.

It absolutely is good to be back, even if I’m having to relearn what day it is sometimes. I’ll post more on what my sabbatical was like later, but if you want to hear my thoughts on it before I took it, you can find those here.

And if what you read interests you at all, a gentle reminder that we are hiring.

As I type this, I have just closed Slack on my main workstation, and I don’t plan on opening it up very often (if at all) for the next three months.

I previously mentioned the benefit at Automattic of the sabbatical every five years of employment, and I’m taking mine starting this weekend. I hope to be blogging a bit about what I’m doing with the time I’m gifted and other things while I am out.

I do have some rough goals for the time I’m out. I’d like to:

  • Take the family on a road trip at some point during the summer.
  • Get in an hour of guitar practice at least three days a week, to focus on just basic learning.
  • Up my CrossFit activity from the current 3 times a week to five times a week.
  • Get another one of my eternally half-baked plugins out there for others to start using.
  • Raise some money for Extra Life prior to my 24-hour marathon for the year, hopefully a good chunk of it. This means more streaming on Twitch!

If I get in even half of that, I’ll feel like I’ve done a good job. I want to use the time to spend it with my family and do more things with my children while they are out of school, but I also want to take the time to level up some skills and improve myself while I’m not in the daily routine.

It’s going to fun! If you want to follow along, following this blog is a pretty good way to do that, or following me on Twitter.

And subscribe to my channel on Twitch!


With the kids home all day long with me, my office tends to be somewhat chaotic. This afternoon, though, it’s my little one sitting next to me watching Netflix on one screen while I work on migrations, launches, and support tickets on the other two.

I spoiled her a bit and gave her some popcorn because I can.


One of the great things about working at Automattic is the feeling that most of us are in it for the long haul.

When I was hired, I distinctly remember Matt telling me as part of that process that he chose to hire people he could see himself working with ten, twenty, maybe even more years down the line. I remember being somewhat surprised at that notion; at the time the longest I had been at a company was approaching four years.

I’ve been at Automattic for five years since this past January. There are a good number of people still at Automattic who have been there for around ten years. I’d venture a guess that for many of us, it is the longest we’ve been employed by a specific company.

It’s clear from how our work and internal policies are structured that this is indeed a focus at Automattic. Not only because of the fully-distributed, work-where-you-like and live-where-you-want nature of the company, but also because our perks have been structured for the long-term health of employees and their relationship with work.

Allow me to explain and tell you about an interesting new addition to those perks that will affect my year in a pretty significant way.

Time Off

Automattic approaches vacation and time off in a very freeform manner. If you need the time off, you coordinate with your team and team lead and you take it as you need it. We don’t have stored PTO hours. You can cut days short or long if you need to for various reasons and you’re encouraged to just do so when necessary and not feel guilty about it.

It’s enormously freeing in terms of making your work fit around your life and vice versa. If I need to schedule a doctor’s appointment or other commitment, I can generally feel free to do so and not have to worry overmuch about work scheduling. Often, I’ll just step away from the desk just for that appointment and then come back and continue working.

I tend to do a mixture of things. It lets me leave for an hour each workday and hit the gym, then just come back and pick things up. I take two weeks off each summer and two weeks off around Christmas every year to rest and take time with my family. And occasional three-day weekends are not unheard of and always welcome.

There is provision for extended leave, as well. If you need a broad bunch of time off for medical reasons or family care reasons, you can take that as you need and if you have been at Automattic for at least a year, it’s fully paid. It’s why I was able to take six weeks away from work after the birth of our most recent child to help her mother and focus on being a dad before returning to the job.

It’s an open and trusting time off setup that gives Automatticians the freedom to focus on their personal health and sanity as well as their family life so they can be more focused on work when we are working.


The other thing we have that’s really cool is that a milestone system is gradually taking shape as we have employees who have been around for longer and longer.

I wrote previously regarding the WordPress-branded laptops we gain access to at our four-year anniversary:

One of the perks of reaching your four-year anniversary is being given a MacBook (Air or Pro) model of your choice, with the WordPress logo customized onto the top cover.

At first, this was a one-time gift when you reached four years, which was really cool because when you hit your next laptop refresh cycle date, you got to keep it permanently. Now, we’ve updated that policy so that every time you have a new laptop coming after your four-year, you can order a new W laptop each time.

I get to keep up with new tech and still have my flashy WordPress laptop all the time. Love it.

The new perk option we have is a combination of a milestone and time off, and it kicks in at your five-year mark, which I just so happened to pass this year.

“Get Away, Renew, and Refresh”

A few weeks ago, the latest milestone was added. Rather than recount it on my own, I asked Lori (our HR lead) if I could post the text of our internal policy on it, and she graciously said I could, so here it is:

If you’ve worked for Automattic for more than 5 years, we encourage you to take a paid sabbatical of 2 – 3 months. Taking an extended leave allows you to break away from the usual routine and return to work refreshed. “What should I do on a sabbatical?” you may ask? You could use the time to fulfill a goal, build a skill, or do research. Or, simply rest and relax. The key is to get away, renew, and refresh.

There’s so much I love about this and how it’s worded. It’s not just that you have the option to take this time off, you are encouraged to do so. You can do whatever you want. And the goal is to take you out of the daily pattern of your work and give you time to restructure and refocus. Automatticians get to take this sabbatical once every five years.

If I want to travel, I can. If I want to just hang out with the kids and play video games, I can. If I want to volunteer and do some rad things to help people, I can do that, too. If I want to take the time to level up some skills, well that’s another perfectly acceptable option.

So when I step back into my role, I’ll bring fresh eyes and hopefully a leveled up skill or two—even if it’s non-technical—to add to my contributions to the team.

That doesn’t mean it’s 100% easy to take this time off—and I’ll discuss that in a future post—but after some discussions with my team leads, I’m definitely going to take that long break this summer to focus on things that aren’t work. I’m not sure what I’ll do yet.

But I know that the time will be well-spent, whether I focus on spending time with my family, learning guitar, going on a road trip, or leveling up my dev skills—or even all of those things. And when I return to my work, I’ll be re-energized for the next five years of working at Automattic.

Maybe you should think about getting started towards that five-year sabbatical, too. We’re hiring.

A couple of Sunday nights ago, I was crouched over my laptop in a rental house in New Orleans working feverishly to help launch Women’s Wear Daily on WordPress.com VIP. It was (and still is) a huge undertaking, and to get it in shape for a successful Monday morning launch, I realized pretty early on Sunday night that I was going to have to pull an all-nighter to get it done.

I did, it launched, got the thumbs-up from all the personalities involved, and I collapsed into bed at around 7:30 a.m. on Monday morning. I was in New Orleans for a team meetup, and spent the majority of the time I was there focused on making sure the pre-and-post-launch processes went as smoothly as possible.

It’s my job, and I take great pride in what I do.

That kind of “crunch” isn’t abnormal in today’s working culture. Long hours, little sleep, and work focus are common. We all know that fatigue and long work hours end up causing less productive work, but sometimes the tasks just need to get done and require sacrifice. What I described may sound like something you have experienced in your work life, and maybe all too recently or all too often.

What I haven’t said yet is why I’m happy to put in those kinds of hours at work when it’s needed. And that’s because I’m happy to work somewhere that respects my time and my life the rest of the time.

When the project was launched, several of my colleagues nudged me and made sure I knew that I should take some time off to make up for the sacrifice of that weekend (and the weeks leading up to it). I was only too happy to oblige, given that I’d already marked today and the two previous days as time off. But it’s notable to be somewhere that recognizes the extra work people put in and then not only allows, but encourages comping that time after the fact with time off to rest and recharge.

And I’ve had a great three days off with my family, spending extra time with them and not worrying about work projects, checking email, or doing anything more than housekeeping check-ins a couple of times over that period to make sure things I’m responsible for are still progressing.

It’s in the time between the days off that Automattic is really special, though. My time and my family are respected by my employer and my colleagues. We have an HR staff and teammates who understand the value of time away from work, even in the middle of the day. I’m very careful to guard my time during the work week. I try to be done for the day around dinner time to spend the evening with me family, I take an hour during the afternoon three times a week to go to the gym and work on my personal fitness level, and I spend my weekends not doing or thinking about work the vast majority of the time.

When my last child was born, I was able to take six weeks off to be a dad and help my wife with her recovery. I take at least two two-week vacations a year to do something fun with the family and not directly think about work stuff. I even take the days off leading into Evo weekend to just enjoy watching some high-level gameplay. If I need a day off, I take the day off.

And this all works because as a team we all know that when things get real, we’re all going to pitch in and do the work that needs to be done. We communicate clearly and often about when we’ll be around and what we’re responsible for. You may find this surprising, but when a company and an employee mutually respect each other’s time, it appears to lead to more dedicated work, less fatigue, and a happier balance.

I know this is something that’s rare—if not unique—and I’m super-appreciative that this job exists and that I’ve been welcomed into it. I’ve been doing this for over five years now and I don’t see myself doing anything else. I think more industries and companies should take a hard look at how we are doing things and think—really think—about changing the face of work for the better. And if what I’ve described sounds like something you’re interested in, maybe you could give our hiring page a quick glance.