Engineering with Empathy

When you supervise a team of engineers hailing from over 40 countries, the way Upwork’s Senior VP of Engineering Han Yuan does, you develop priceless knowledge about how distributed teams work. According to Han, the crux of the challenge is setting expectations with every team member. Doing this well requires maintaining a consistent culture, along with regular, frequent, and — most of all — clear communication. 

What does it mean to maintain a consistent culture? Han calls this a “very difficult problem” when applied to distributed teams. 

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How to do HR in a Blended Company

Upwork is the largest freelancing platform, operating across 180 countries. It’s a company that deals in human resources, so its own HR department needs to model best practices. Upwork’s Head of Human Resources and Talent Innovation, Zoe Harte, keeps the department at the cutting edge. Making sure that the right people in the right places are equipped with the skills and tools they need to perform at a high level requires strategic decision-making, so it makes sense that the person responsible for that core work would serve much more than an administrative role.

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Transcript: Upwork’s Zoe Harte and Han Yuan

Read more about Zoe Harte in “How to do HR in a Blended Company” and about Han Yuan in “Engineering with Empathy.”

MATT MULLENWEG: Back in June we had the pleasure of speaking with Stephane Kasriel, the CEO of Upwork, the world’s largest freelance marketplace. Stephane laid out a compelling case for the distributed model as a way for talent-starved companies in expensive, crowded cities to do business with workers who live in places with comparatively sluggish economies.

But Upwork’s not just thinking about this in theoretical terms: they practice what they preach, with a distributed workforce of their own. In this episode, we’ll talk to two Upwork employees from two very different practice areas who give us glimpses of how their company does distributed. 

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On Building Automattic

Launching the Distributed podcast has given me space to reflect on the last 14 years at Automattic. In 2019, distributed work has spread throughout the Bay Area and beyond, but when we were getting started, having no corporate headquarters was seen as quirky. Our distributed status has come to define our company, but we didn’t set out to be distributed. It was common in open source projects and our initial team was spread around the world. But over time it became who we are. 

I’m originally from Houston, Texas. In 2003, web developer Mike Little and I, along with a few other online friends, developed a web publishing tool called WordPress. It quickly became popular, but we had no inkling that it could ever be a revenue-generating project. We just wanted to make better publishing tools so that non-engineers could express themselves online with their own blogs. For me, it was satisfying simply to hang out on IRC (an early chatroom protocol) with smart, curious people working on an interesting collaboration. I was spending all my free time online, hanging out and coding with people all over the world, having an absolute blast. 

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Transcript: Episode Four, Matt Mullenweg

Read Matt’s history of Automattic: “On Building Automattic.

Distributed Podcast: Hear Matt Mullenweg in conversation with Mark Armstrong.

Mark Armstrong: Hi everybody. Thanks for joining the Distributed podcast. I’m not Matt Mullenweg, I’m Mark Armstrong. I’m the founder of Longreads, which is part of Automattic, and I’m on the editorial team working with Matt on the Distributed Podcast.

So today I wanted to take a step back from the interviews Matt’s been doing and find some context for how Matt got here in the first place, how he became interested in distributed work, and it all starts with the history of Automattic. So that’s what we’re going to talk about today. We’re going to talk to Matt about how he got here, how he actually decided to build a company that had no offices, and what worked and what didn’t. Thanks for listening.

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Transcript: Episode Three, Arianna Simpson

Read more about Arianna Simpson in “Is Remote Work Bull***t?”


Distributed Podcast: Hear Matt Mullenweg in conversation with Arianna Simpson.

MATT MULLENWEG: Back in March, Arianna Simpson tweeted an offhand remark that went crazy viral.

“Unpopular Opinion: Remote work is mostly bullshit.”

Arianna had no idea that thousands of people would like the tweet, and hundreds would weigh in with their thoughts, some pushing back, others hailing the blunt honesty of her “unpopular opinion.” As a true believer in distributed work, I naturally had to get in touch with Arianna when I saw the tweet.

Arianna is an early stage investor, with close to 40 investments to date, many of which deal with the blockchain and cryptocurrency projects. I wanted to find out: How is it that someone, who knows so much about distributed software that’s created among globally-distributed teams, has such a pessimistic view of distributed work?

It turns out, as it often does, that Arianna’s thoughts on distributed work are more nuanced than her tweet might lead you to believe. We discuss her reservations with remote work, we cover some of the things that traditional office arrangements are really good at providing workers, and we explore how companies can give their employees the best of both worlds with a hybrid model.

But things really get cooking when we started talking about how the blockchain could one day be used by distributed companies to pay workers in far-flung locations with stablecoins that are pegged to a traditional currency. When money becomes programmable, all kinds of interesting contracts and financial arrangements open up, making it easier than ever for the distributed company of the future to partner with workers all over the world.


ARIANNA SIMPSON: My name is Arianna Simpson and I run a fund called ASP. I’ve been an investor for the past several years, first general VC, and now running a crypto-specific fund.

Matt: So you’re into distributed systems.

Arianna: I am.

Matt: One of the reasons I really appreciate you coming on — and a goal of this podcast is — I wanna have the very best versions of why people should be in the same place, as well as making the case for distributed work. We are obviously in the same place right now.

Arianna: Yes, we are.

Matt: We are in a tiny studio in New York City, and this is nice, right? Because we’re having a higher-fidelity communication.

Arianna: Mhm.

Matt: This all started in a tweet. Do you remember the tweet?

Arianna: The tweet heard round the world! Oh yes, it was kind of Paul Revere-ish in its quality in that sense.

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Is remote work ‘Bull***t’?

We believe that distributed work is great for many reasons, and will eventually replace most traditional office environments. But an important part of treating distributed work seriously is discussing its downsides and the hurdles it presents to teams and individuals. To better understand the concerns around the distributed work model, Matt recently spoke with venture capitalist Arianna Simpson, a vocal skeptic of remote work.

It’s difficult to know what kinds of statements are going to make a big splash on social media. Brands spend untold resources trying to learn how to “start a conversation,” but usually the tweets that go viral are offhand remarks that were never conceived as definitive statements.

Such was the case with venture capitalist Arianna Simpson’s “tweet heard ‘round the world,” as she calls it. She set out to share a casual thought with her audience, but something about her perspective touched a nerve:

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Transcript: Episode Two, John Vechey

Read more about John Vechey in “For Years, VR Promised to Replace the Office. Could It Really Happen Now?

Distributed Podcast: Hear Matt Mullenweg in conversation with John Vechey.

Matt Mullenweg: We’ve been hearing about virtual reality since the late ’80s, but this technology still hasn’t yet leapt from the pages of science fiction into our universe—at least not into the mainstream. The VR revolution seems to be always just around the corner, but some people believe that we really are on the verge of something that’s going to change everyone’s lives.

John Vechey, cofounder of Pluto VR, is one of those people. He’s specifically interested in how VR is going to change the way we communicate. John found success as the founder of PopCap Games–you may know them as the folks behind your favorite mobile games like Bejeweled or Plants vs. Zombies. After selling PopCap, he transitioned into virtual communications.

I wanted to speak with John because he’s got some big ideas about how VR will one day be used for work.

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For Years, VR Promised to Replace the Office. Could It Really Happen Now?

Those of us who work on distributed teams have become accustomed to a workplace tool that, even after almost two decades, still feels very sci-fi. It’s cheap, it’s seamless, and it’s ubiquitous: video chat.

Chatting with video has long felt like an inevitability; it’d been featured in popular culture since at least the advent of the telephone. From The Jetsons to Star Trek, many of our utopian visions of the future involved the simple but rather magical concept of broadcasting your face across the globe, if not the galaxy.

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Transcript: Episode One, Stephane Kasriel

Read more about Stephane Kasriel in “The American Dream Is Broken, and I Think We Have a Shot at Fixing It.

Distributed Podcast: Hear Matt Mullenweg in conversation with Stephane Kasriel.

Matt: To start off, say your name and how long you’ve been here, just so people have a sense of you. And then we’ll talk.

Stephane: Sure. So my name is Stephane Kasriel, I’m the CEO of Upwork. I joined the company close to seven years ago. Initially I was running product management and design and then when our head of engineering left, I became the head of product management, design and engineering. And then a couple years later, when the CEO left, I got promoted and became the CEO of the company. And that was about four years ago.

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