Distributed Work’s Five Levels of Autonomy

I recently had the opportunity to sit down with Sam Harris, author and host of the Making Sense podcast, for a wide-ranging conversation. Given the moment we’re currently living through, we naturally touched on the way companies are adapting to a new reality — one where remote work is a model to which they must adapt in a matter of days, rather than years.

As I mentioned to Sam on the podcast, “any company that can enable their people to be fully effective in a distributed fashion, can and should do it far beyond after this current crisis has passed.” It’s a moral imperative. But that doesn’t mean it’s going to be easy, or that the chaotic and stressful first taste some workplaces are getting right now is one that inspires them to keep trying.

To make sense of this journey — from a company’s cautious exploration of remote possibilities to a fully realized distributed experience — I like to think of how it plays out through the concept of levels of distributed work, which I modeled after self-driving car levels of autonomy. I’ve seen some solid recaps of my conversation with Sam from Steve Glaveski and Steve Jurvetson, but here’s my gist of how distributed companies evolve:

  1. Level Zero autonomy is a job which cannot be done unless you’re physically there. Imagine construction worker, barista, massage therapist, firefighter… Many companies assumed they had far more of these than it has turned out they really did.
  2. The first level is where most colocated businesses are: there’s no deliberate effort to make things remote-friendly, though in the case of many knowledge workers, people can keep things moving for a day or two when there’s an emergency. More often than not, they’ll likely put things off until they’re back in the office. Work happens on company equipment, in company space, on company time. You don’t have any special equipment and may have to use a clunky VPN to access basic work resources like email or your calendar. Larger level one companies often have people in the same building or campus dialing into a meeting. Level one companies were largely unprepared for this crisis.
  3. Level two is where many companies have found themselves in the past few weeks with the COVID-19 pandemic. They’ve accepted that work is going to happen at home for a while, but they recreate what they were doing in the office in a “remote” setting, like Marshall McLuhan talked about new media mediums initially copying the generation before. You’re probably able to access information from afar, you’ve adapted to tools like Zoom or Microsoft Teams, but everything is still synchronous, your day is full of interruptions, no real-time meetings have been canceled (yet), and there’s a lot of anxiety in management around productivity — that’s the stage where companies sometimes install surveillance software on laptops. Pro tip: Don’t do that! And also: Don’t stop at level two!
  4. At the third level, you’re really starting to benefit from being remote-first, or distributed. That’s when you see people invest in better equipment — from a good desk lamp to solid audio gear — and in more robust asynchronous processes that start to replace meetings. It’s also the point at which you realize just how crucial written communication is for your success, and you start looking for great writers in your hiring. When you are on a Zoom, you often also have a Google Doc up with the other meeting participants so you can take and check real-time notes together. Your company has a zero-trust BeyondCorp security model. In a non-pandemic world you plan meetups so teams can break bread and meet each other in person a week or two a year.
  5. Level four is when things go truly asynchronous. You evaluate people’s work on what they produce, not how or when they produce it. Trust emerges as the glue that holds the entire operation together. You begin shifting to better — perhaps slower, but more deliberate — decision-making, and you empower everyone, not just the loudest or most extroverted, to weigh in on major conversations. You tap into the global talent pool, the 99% of the world’s population and intelligence that doesn’t live near one of your legacy physical office locations. Employee retention goes way up, and you invest more in training and coaching. Most employees have home-office setups that would make office workers green with envy. You have a rich social life with people you choose. Real-time meetings are respected and taken seriously, almost always have agendas and pre-work or post-work. If you get good at baton passes work will follow the sun 24/7 around the world. Your organization is truly inclusive because standards are objective and give people agency to accomplish their work their way.
  6. Finally, I believe it’s always useful to have an ideal that’s not wholly attainable — and that’s level five, Nirvana! This is when you consistently perform better than any in-person organization could. You’re effortlessly effective. It’s when everyone in the company has time for wellness and mental health, when people bring their best selves and highest levels of creativity to do the best work of their careers, and just have fun. 🤠

A highly influential book for me in designing Automattic was Daniel Pink’s Drive, where he eloquently introduces the three things that really matter in motivating people: mastery, purpose, and autonomy. Mastery is the urge to get better skills. Purpose is the desire to do something that has meaning, that’s bigger than yourself. These first two principles physically co-located companies can be great at. But the third, autonomy, is where even the best in-office company can never match a Level 4 or above distributed company.

Autonomy is our desire to be self-directed, to have agency over ourselves and our environment. Close your eyes and imagine everything around you in a physical office: the chair you’re in, the desk, distance from a window, the smells, the temperature, the music, the flooring, what’s in the fridge, the comfort and privacy of the bathrooms, the people (or pets) around you, the lighting. Now imagine an environment where you can choose and control every one of those to your liking — maybe it’s a room in your house, a converted garage, a shared studio, or really anything, the important thing is you’re able to shape the environment fit your personal preferences, not the lowest common denominator of everyone an employer has decided to squish together for 8 hours a day. The micro-interactions of the hundreds of variables of your work environment can charge you and give you creative energy, or make you dependent, infantilized, and a character in someone else’s story. Which do you want to spend half of your waking workday hours in?

For a good summary of Dan Pink, check out this animation. The other books I referenced in the podcast are Geoffrey West’s Scale and Nassim Nicholas Taleb’s Antifragile.

My talk with Sam covered many other topics, from communicating in distributed companies to the challenges businesses are facing due to COVID-19, so I hope you head over and listen to the rest or stream it on Youtube.

Don’t Mute, Get a Better Headset

One heterodox recommendation I have for audio and video calls when you’re working in a distributed fashion is not to mute, if you can help it. When you’re speaking to a muted room, it’s eerie and unnatural — you feel alone even if you can see other people’s faces. You lose all of those spontaneous reactions that keep a conversation flowing. If you ask someone a question, or they want to jump in, they have to wait to unmute. I also don’t love the “unmute to raise your hand” behavior, as it lends itself to meetings where people are just waiting their turn to speak instead of truly listening. I’m always hesitant to disagree with Seth Godin, but that’s been my experience.

So what should you do? Use the latest and greatest hardware and software to have the best of both worlds, a fantastic auditory experience for you and your interlocutors and little to no background noise.

To summarize, I recommend a wired, USB headset with a mic that stays a constant distant from your mouth and has a noise-canceling microphone. Save mute for coughs and sips of drinks.

The rest of this post I’m going to try out eleven different microphones and headsets, ranging from $35 to $1,000+, and record a short file on each, and intersperse some software tips for people on MacOS. You may want to listen to these samples with good headphones on to really hear the differences. I apologize some are louder than others, I didn’t edit to even out the levels, which Zoom or Skype would do automatically.

My previous top recommendation was the trusty Sennheiser SC 30, in my previous bag posts. It’s cheap and effective, but the cord was too long and it was USB-A. If you read no further, get this one and revolutionize how you sound on Zoom calls. Here’s how it sounds:

Sennheiser has upgraded to a USB-C version, with a much shorter cord, the SC 130. It feels and looks much better, you don’t need a USB-C dongle, and the sound quality of the earphones is quite bearable. The cost is about twice as much (~$70).

You can plug the USB-C into your iPad or Android phone as well and it works great, though the headphones can be a bit quiet on Android. Either of the above will spoil you for making calls, and you won’t want to go back to the old low-fi way of doing things.

In order to have a bit more flexibility I tried out the much more expensive ($134) Sennheiser MB Pro 1. I liked the freedom of wireless Bluetooth, but you can hear that the sound is much worse. Connecting over Bluetooth lowers the quality a ton, and also occasionally means you need to disconnect, reconnect, etc.

All three of the Sennheisers above come in two-ear versions, which I prefer if I’m in a noisy environment, but at home I find the one-ear a bit more comfortable. I got excited about this $70 TaoTronics “Trucker Bluetooth” headset because it had Bluetooth 5.0 so I foolishly assumed it would have better quality, but it sounds really terrible:

But does wireless have to mean terrible quality? The Apple Airpods Pro ($249) are actually pretty decent, and you can easily switch them between your phone and your computer in the audio menu. If you haven’t tried the Pro version, the noise canceling is actually pretty amazing for something so small and light — I jog with them.

And one of the best sounding mics in this entire roundup was the wireless $119 Antlion Audio ModMic Wireless, which sound amazing, but you have to provide your own headphones to attach it to, and the entire thing ends up being fairly bulky and has its own wireless adapter. On the plus side, you can bring your own super-fancy headphones and get amazing audio quality. With certain headphones it did cause a buzz in the ear of the headphone I attached it to.

But hot dang that sounds good. If they made an over-the-ear USB-C version with an earbud, and had the mic be a little smaller, it would be work-from-home nirvana.

I ventured into the gaming headset territory for this SteelSeries Arctis Pro Wireless Gaming Headset, which at first felt totally ridiculous with its own connector box, a million cables, etc, but goshdarnit grew on me. It has this really cool boom mic that extends out, and I think it’s the most comfortable headset I’ve worn for an extended amount of time. I tried it out via its proprietary 2.4ghz wireless connection + USB, and Bluetooth, and unfortunately the results weren’t great, including the Bluetooth being a little garbled. I hope Steelseries does another iteration because they’re so close, it just needs to be USB-C on the headphones, the cables, the everything, and super high quality recording.

One final entrant — how about just your laptop? Normally I would say this sounds terrible and judge people who didn’t use a headset, but John Gruber’s review of the new Macbook 16 had some really impressive audio files that intrigued me, so here it is, the Macbook Pro 16″, which starts at about $2,400. It’s a little boomy, but not bad.

Okay now let’s get a little crazy. Here’s a Zoom H5 with the SGH6 shotgun mic attachment. (The other Zoom! $410 total.)

Next up is the Shure SM7B Cardioid Dynamic, which is what I usually use to record the Distributed podcast, and costs about $400. This is milky and smooth. (I accidentally called it a Sennheiser in the recording.)

A favorite of voiceover artists everywhere is the Sennheiser MKH416 Super-Cardioid Shotgun Tube Condenser ($1,000), which I like the sound of and I also use for if I’m doing a fancy video setup and want super-good sound that’s not in the frame of the camera.

It’s a great sound, but the part of the house where I recorded all of these is pretty noisy with an AC unit on the other side of the wall, and there’s a ton of background noise in this.

Software eats the audio world

Just like photography has been completely transformed by software enhancing images to the point where the top-of-the-line Apple or Samsung smartphone camera is better than all but the very top pro SLR cameras, I think the same thing is going to happen for audio.

None of these clips are processed, which is why some of the volume levels are different, but I thought it would be fun to demo a tool I’ve been recommending to a lot of people.

There’s a $40/year program called Krisp.ai, which I first learned about in 2018 from this awesome post on the Nvidia developer blog, Real-Time Noise Suppression Using Deep Learning. What it does is create a virtual microphone, like a filter that exists between one of your physical inputs and what the software on your computer “hears.” For fun I re-recorded the MKH416 in the exact same place, but filtered through Krisp.ai:

Now the audio quality is not as good, it sounds a bit clipped, but throughout there is no more distracting background hums or noise. Krisp can be a little awkward to use but they’ve made it a lot more user friendly. You could mix Krisp with almost any option here and it would make it sound much better, in fact when I’m in a pinch my favorite go-to is Airpods Pro + Krisp.

With everything, a pro tip on MacOS is to hold Option when you click on the sound icon in your upper right taskbar, and it will let you select both input and output devices. Sound Preferences, linked at the bottom of that menu, are your friend. If a mic is too soft you can boost the input volume in the preferences. To choose a camera or mic in Zoom, click the arrow next to the mute button in the bottom left. In Zoom audio settings, under Advanced, they are starting to expose a number of new options for real-time audio processing.

The future sounds good.

I’ve really had enough of this term “social distancing.” That is not at all what we are looking for, is it? It should be “physical distancing.” In these times of rampant loneliness (especially for seniors), disconnection, and lack of empathy and compassion, we need the opposite — social connecting. And we need it under these circumstances more than ever. Let’s be creative in finding new ways to come together.

Adam Gazzaley, M. D., Ph. D, University of California, San Francisco

Update: On March 20th, the World Health Organization has officially updated it’s recommendation to “physical distancing.”

Business as Usual in The Information

The Information wrote Business as Usual — Remotely, which includes “85% of its 900 employees working from their homes” Hashicorp, which just raised $175M at a $5.1B valuation today. (I have to get them on Distributed.) Here’s my part:

A survey of American workers by the polling firm Gallup found that in 2016 43% of employees worked remotely at least some of the time, up from 39% in 2012. Of those remote workers, almost a third spent 80% or more of their time working remotely in 2016, compared to 24% in 2012. In computer-related professions, 57% did some remote work in 2016, according to Gallup. 

That includes tech companies like Automattic, which makes WordPress and other software products and has been almost entirely remote since it was founded in 2005. At one point, it opened a large office in San Francisco for employees who preferred a more traditional work environment, but it got rid of that space in 2016 because of how little people used it.  

“We had this 15,000-square-foot place with only five people coming into it,” said Matt Mullenweg, CEO of Automattic, which acquired Tumblr last year. 

Now Automattic rents only one small co-working space in a WeWork suite in New York  and uses another small office in San Francisco exclusively for board meetings. It manages its remote workforce using Slack and Zoom and gives new employees $2,000 so they can purchase home office equipment. 

Employees can also get up to $250 per month for access to a co-working space or for daily coffees at a local coffee shop. But Mullenweg says only about 300 of the company’s 1,200 employees chose to work somewhere other than a home office.

“I hope there can be a silver lining to this crisis, which we all hope is over as soon as possible, that enables people to reexamine how they work and how they interact with things and improve it,” said Mullenweg. “I’m happy to spread the gospel wherever possible for distributed work. I think it’s better for companies, employees, the environment and the world. There are very few downsides.” 

The Information is a worthwhile subscription if you’re in the tech business.

Coronavirus and the Remote Work Experiment No One Asked For

“We’ll never probably be the same. People who were reticent to work remotely will find that they really thrive that way. Managers who didn’t think they could manage teams that were remote will have a different perspective. I do think we won’t go back.”

Jennifer Christie, Twitter’s head of human resources, in BuzzFeed News

This is not how I envisioned the distributed work revolution taking hold.

It has been a challenging time around the world—from how we live our daily lives to how we keep our kids safe in schools and our family members healthy in assisted living communities and hospitals. 

And then there’s how we work. Seattle (and all of King County in Washington State) is encouraging companies to have their employees work from home. Given that Automattic is already distributed, we’re receiving requests from the press and other companies about how to navigate what is turning into a massive global work-from-home experiment. 

It’s not ideal on any level. Even at a remote-friendly company like Automattic, we rely on in-person team meetups and conferences to strengthen our connections and get work done. For now, we’ve canceled all work-related travel.

But as the BuzzFeed story notes, this might also offer an opportunity for many companies to finally build a culture that allows long-overdue work flexibility. Millions of people will get the chance to experience days without long commutes, or the harsh inflexibility of not being able to stay close to home when a family member is sick. 

Or even when you’re sick yourself. How many people in America go into an office even when they’re feeling under the weather, because of pressure from the company or managers, or because their sick days come out of their vacation days? This might be a chance for a great reset in terms of how we work. 

For those asking for tips, my Distributed Podcast has a wealth of advice and stories about how we operate. But here are four good ones to start with: 

  1. Operate as if everyone works from different time zones, because one day they might. This means more communication, likely written, that is accessible to people even if they can’t attend a specific meeting or be in a specific place. If you can minimize the number of real-time meetings, do so. Embrace asynchronous communication.
  2. If you are hosting a real-time meeting, improve the audio (and video) quality. Don’t use conference call lines with grainy phone audio. Sign up for Zoom, which allows for crystal clear audio calls or videoconference chats. Make video participation optional unless it’s planned well in advance. Record these calls so folks who can’t attend can catch up on what they missed. Everyone must use good headphones with mics (I love Sennheiser) to minimize external noise. Krisp.ai is also cool. Need a quiet place without distractions? Try a parked car or a closet.
  3. We use our own WordPress blogs, called P2, instead of email as our central hub of communication so people throughout the company can access every team’s long-form notes, documents, and priorities. We’re bloggers by heart, so we blog a lot. There are other similar tools, like Basecamp. Make it your new office.  
  4. We also use Slack for real-time chat, social connection, and urgent conversations. Check out Matrix for an open-source, distributed version. Use it to chat and connect with your colleagues, but don’t let it replace your long-form planning notes in No. 3. Also create an etiquette that doesn’t force people to become chained to it all day and all night. When you ask a question in DM, do not expect that person to respond immediately, and ask your question upfront. Never write “got a sec?” and let it hang there. 😁

The truth is, there are a thousand ways to do remote work, but it starts with committing to it at all levels of the company. If you assume positive intent and place trust in your coworkers and employees—knowing that if they do great work in an office they can do great work anywhere—then you will all succeed. 

Livestream Tomorrow

About eight of the speakers including myself are going to be doing a livestream tomorrow from 2 to 10 UTC, or what would be 9am to 5pm in Bangkok where the inaugural WordCamp Asia was supposed to happen this weekend.

We’d all much rather be in person, but I do think there is a silver lining in us learning how to do official WordPress livestream events that can be accessible to everyone all over the world, following in the footsteps awesome virtual events like WordSesh.

Thirty Six

I am now solidly entering my late thirties, and fortunately I am in good health, good cheer, and doing one of my favorite things — exploring a part of the world and culture I haven’t experienced before (Maldives and Sri Lanka).

The past year has included a number of professional milestones including a significant amount of fundraising and related activity, bringing in a major new product to the Automattic family, the maturation of Gutenberg in the WordPress ecosystem, launching the Distributed blog and podcast, and a growth in the breadth and depth of the Automattic team.

Partially because of the schedule those milestones required, this ended up being my year with the most travel ever since I started tracking: I flew over 515k miles, to 124 cities in 24 countries. I was able to incorporate a good amount of running in my routine, started picking up musical instruments again, and learning more about sound and its impact on our lives. I found small daily habits, like a little bit of exercise or stretching first thing in the morning, to be sustainable and high-impact.

What suffered in 2019 was my book reading time and making a dent on the top 50 list. I still check tech news every day, but I had to unplug from daily non-tech news because it was just too hectic — I’ve found a lot of value in weekly publications like the Economist to make sense of what’s going on in the world with the benefit of a little distance and time.

Personally my main goals this year are for the health and wellness of my family, incorporating more playing music and photography into my life, and strengthening my meditation practice. If you’re reading this, I hope to run into you online or in person and this year let’s do our best together to leave the world a little better than we found it.

All birthday posts: 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40.

29 Books in 2019

As a follow-on to my lists in 2017 and 2018, here are the books I completed this year. I’ve linked all to the Kindle edition except the Great Mental Models, which is so gorgeous in hardcover you should get that one, and the The World is Sound isn’t available as an ebook. Bold are ones I particularly enjoyed or found myself discussing with others a lot.

  1. The Pilgrimage by Paulo Coehlo
  2. 21 Lessons for the 21st Century by Yuval Noah Harari
  3. No Longer at Ease by Chinua Achebe
  4. Imagine it Forward by Beth Comstock
  5. The Great Mental Models Vol. 1 by Shane Parrish
  6. Why Buddhism is True by Robert Wright
  7. There Will Be No Miracles Here by Casey Gerald
  8. Less by Andrew Sean Greer
  9. Bad Blood by John Carreyrou
  10. nejma by Nayyirah Waheed
  11. Trust Exercise by Susan Choi (also on Obama’s book list, and based on the high school I went to, HSPVA)
  12. Genghis Khan and the Making of the Modern World by Jack Weatherford
  13. The Way to Love by Anthony de Mello
  14. The Fifth Agreement by Don Miguel Ruiz, Don Jose Ruiz, and Janet Mills
  15. Empty Planet by Darrell Bricker
  16. Brave New World by Aldous Huxley
  17. How to Talk So Kids Will Listen & Listen So Kids Will Talk by Adele Faber and Elian Mazlish
  18. Make it Scream, Make it Burn by Leslie Jamison
  19. A Short History of Progress by Ronald Wright
  20. Conscious: A Brief Guide to the Fundamental Mystery of the Mind by Annaka Harris
  21. The World Is Sound: Nada Brahma: Music and the Landscape of Consciousness by Joachim-Ernst Berendt
  22. The 15 Commitments of Conscious Leadership by Jim Dethmer and Diana Chapman
  23. Finite and Infinite Games by James P. Carse
  24. Four Soldiers by Hubert Mingarelli
  25. Working by Robert Caro
  26. Attached by Amir Levine and Rachel Heller
  27. Skin in the Game by Nassim Nicholas Taleb
  28. The Devil’s Financial Dictionary by Jason Zweig
  29. How to Do Nothing: Resisting the Attention Economy by Jenny Odell (also on Obama’s book list)

What’s interesting is that if you were to purchase every single one of those books, it would be about $349. You could get them all for nothing from your local library, even on a Kindle. The money I spend on books is by far and away the best investment I make every year — books expand my mind and enrich my life in a way that nothing else does.

Comments and Collatz Conundrum

Over the summer Terence Tao, a Fields Medal-winning mathematician considered one of the best of his generation, got an anonymous comment on his WordPress blog post from 2011 exploring the Collatz conjecture — one of the most persistent problems in math — suggesting he explore the problem for “almost all” numbers. Terence has been a regular WP.com blogger since 2007 and he and his commenters make extensive use of our LaTeX feature to express and embed equations.

That anonymous comment led him to an important breakthrough on the Collatz Conundrum, as Quanta Magazine reports. If you want great comments, you as the author have to participate in them and Terence is incredibly active in engaging with the commenters on his site.

I’ve always said that comments are the best part of blogging, but this is a particularly cool example. Here’s Terence’s latest post on it, with an excellent comment thread following.

Distributed Podcast: Clark Valberg, Lydia X. Z. Brown, Stephen Wolfram, and the Grand Meetup

If y’all haven’t caught up recently with my podcast Distributed, this is a perfect moment to do so—the past several weeks have been full of insights from folks like InVision CEO Clark Valberg, attorney and advocate Lydia X. Z. Brown, Stephen Wolfram, and some of my own Automattic colleagues in-person at our Grand Meetup.

You can subscribe at Apple Podcasts, Google, Overcast, Spotify, or wherever you like to listen. 

Continue reading Distributed Podcast: Clark Valberg, Lydia X. Z. Brown, Stephen Wolfram, and the Grand Meetup
Great Mental Models book cover

Farnam Street’s Great Mental Models, Presented by Automattic

I’ve been a fan of Shane Parrish and his indispensable Farnam Street for many years now. Shane is a fascinating person — he’s a former cybersecurity expert for the Canadian intelligence agency and occasional blogger who turned his website into a full-time career. Oh and fs.blog is on WordPress, too. 😎

His book, The Great Mental Models: General Thinking Concepts, has been tremendously valuable to me in my work. So valuable, in fact, that Automattic is now sponsoring the next printing of the hardcover edition. You can pre-order it here, then learn more about the mental models outlined in it.

State of the Word 2019

In case you missed it, here’s the first-ever State of the Word… designed completely in Gutenberg:

WordCamp US was a fantastic experience, as always. Thank you again to the hundreds of organizers and volunteers who made it happen, to the thousands who attended, and to the city of St. Louis for hosting us. We’ll be back there again next year.

And special thanks to this next generation of WordPress contributors. So exciting to see KidsCamps continue to expand and thrive:

As you can see, my site is now featuring the new WordPress Twenty Twenty theme. And for more coverage from my State of the Word, check out the recaps from WP Tavern and Post Status. Here’s my full audience Q&A below:

You can see my previous State of the Word keynotes here.

New Automattic CFO

As Venturebeat has picked up, Mark Davies will be leaving Vivint and joining the merry band. Automattic is creating the operating system for the web, from websites to ecommerce to social networks. As we zoom past 1,100 employees in over 70 countries, we wanted a financial leader with experience taking businesses from hundreds of millions in revenue to billions (Vivint) and even tens of billions (Alcoa and Dell), as Mark has. I’m excited about working alongside such an experienced leader day-to-day to build what I hope will become one of the defining technology companies of the open web era.

Debating OSS with DHH

The other week I ended up going back and forth in tweets with David Heinemeier Hansson, it wasn’t going anywhere but he graciously invited me to their podcast and we were able to expand the discussion in a way I found really refreshing and mind-opening.

DHH and I have philosophies around work and open source that I believe overlap 95% or more, so that makes where we have differences all that more interesting to mine. Although we would see each other logged into the same server 15 years ago, we haven’t actually spoken directly until this podcast started, but the conversation flowed so naturally you’d think we have been talking since then.

Check out the episode on Open Source and Power on the Rework Podcast, hopefully you enjoy listening as much as we enjoyed recording it.

Automattic’s Series D

Today Automattic announced it has closed a new $300 million Series D, with Salesforce Ventures taking the entire round. This puts us at a post-round valuation of $3 billion, three times what it was after our last fundraising round in 2014. It’s a tremendous vote of confidence for Automattic and for the open web.

I met Marc Benioff earlier this year, and it became obvious to both of us that Salesforce and Automattic shared a lot of principles and philosophies. Marc is a mindful leader and his sensibilities and sense of purpose feel well aligned with our own mission to make the web a better place. He also helped open my eyes to the incredible traction WordPress and WP VIP has seen in the enterprise market, and how much potential there still is there. I’ve also loved re-connecting with Bret Taylor who is now Salesforce’s President and Chief Product Officer. Bret’s experience across Google Maps, Friendfeed, Facebook, Quip, and now transforming Salesforce makes him one of the singular product thinkers out there and our discussion of Automattic’s portfolio of services have been very helpful already.

For Automattic, the funding will allow us to accelerate our roadmap (perhaps by double) and scale up our existing products—including WordPress.com, WordPress VIP, WooCommerce, Jetpack, and (in a few days when it closes) Tumblr. It will also allow us to increase investing our time and energy into the future of the open source WordPress and Gutenberg.

The Salesforce funding is also a vote of confidence for the future of work. Automattic has grown to more than 950 employees working from 71 countries, with no central office for several years now. Distributed work is going to reshape how we spread opportunity more equitably around the world. There continue to be new heights shown of what can be achieved in a distributed fashion, with Gitlab announcing a round at $2.75B earlier this week.

Next year Automattic celebrates 15 years as a company! The timing is fortuitous as we’ve all just returned from Automattic’s annual Grand Meetup, where more than 800 of us got together in person to share our experiences, explore new ideas, and have some fun. I am giddy to work alongside these wonderful people for another 15 years and beyond.

If you’re curious my previous posts on our fundraising, here’s our 2006 Series A, 2008 Series B, 2013 secondary, and 2014 Series C. As before, happy to answer questions in the comments here. I also did an exclusive interview with Romain Dillet on (WP-powered) Techcrunch.

Tumblr the Day After

It is not surprising that the news about Automattic buying Tumblr has picked up a lot of coverage. I especially appreciated the notes of support from Tumblr founder David Karp, former CTO Marco Arment, and investor Bijan Sabet. I am beyond excited to see what the Tumblr team creates next, and I will definitely be connecting with alumni to hear their perspective.

There has also been a lot of speculation on the purchase price, which I think is missing the real story. I would like to take this opportunity to express my respect for Verizon and how they approached this entire process. They inherited Tumblr through an acquisition of a merger, a few steps removed from its initial sale; it’s probably not a company they would have bought on its own, but they nonetheless recognized that there is a very special community and team behind the product. It’s also worth noting at this point that Verizon is a company that will do over $130B in revenue this year and has over 139,000 employees.

First, they chose to find a new home for Tumblr instead of shutting it down. Second, they considered not just how much cash they would get on day one, but also — and especially — what would happen to the team afterward, and how the product and the team would be invested in going forward. Third, they thought about the sort of steward of the community the new owner would be. They didn’t have to do any of that, and I commend them for making all three points a priority.

Automattic is still a startup — I’m sure there are deep-pocketed private equity firms that could have outbid us, but the most likely outcome then would have been an “asset” getting chopped up and sold for parts. (This is a caricature and there are PE firms I like, but it’s not a terrible stretch of the imagination.) Instead, Tumblr has a new chance to redefine itself in 2019 and beyond. Its community is joining with WordPress’ 16-year commitment to open source and the open web.