The Distributed Podcast is an in-depth conversation about the future of work — with the companies and leaders driving it. Hosted by Co-Founder of WordPress and CEO of Automattic Matt Mullenweg. Subscribe.
On this episode of Distributed, we dig into the good, the bad, and the karaoke-filled history of Automattic meetups. Before the COVID-19 pandemic, our annual Grand Meetup brought the entire company together for a week. The time spent together — along with team-specific meetups scattered throughout the year — helped us strengthen relationships with our colleagues located around the world. Now, as companies and workers grapple with returning to the office, it’s a perfect chance to consider in-person time as an important complement to the autonomy and flexibility of distributed work.
We spoke with Automatticians about how to stay connected in a distributed work culture. You’ll hear from Toni Schneider, Automattic’s first CEO, Josepha Haden Chomphosy, Executive Director of the WordPress Project, and Nick Gernert, CEO of WordPress VIP, along with a wide range of Automatticians.
The full episode transcript is below and has been lightly edited for clarity.
Nearly ten years ago, Dylan Field and Evan Wallace turned a Thiel Fellowship into a solution to the ‘single source of truth’ problem for design systems.
Their interest in design collaboration and WebGL laid the foundation for the origin story of Figma, today’s ubiquitous browser-based design tool — and rapidly-growing company.
“The more (we) pulled this thread, the more we learned there’s so much to do in terms of making design better, and in making it so more people can access design within the organization,” says Dylan of their early pursuis. (Spoiler: drone technology was a runner up in their technology explorations).
The latest episode of the Distributed podcast pairs Dylan, Figma’s CEO and Co-founder, and guest host Connie Yang, Head of Payments Design at Stripe, with past design leadership posts at Coinbase and Facebook.
Connie’s passion — uncovering the bits of magic surrounding us in everyday life — guides their friendly dialogue from design to remote culture and much more. Early in the show, Dylan shares what he’s learned about instilling culture in a rapidly-growing company, especially amid the changes brought on by the pandemic. “The main thing that changes once you go from in-person to remote is you can no longer rely on physical context to instill culture,” says Dylan. “It matters even more to elevate the role of design, and elevate anything you think is really important in that digital context.”
Dylan also builds on a recurring Distributed podcast theme over the past year, adding “It’s really important to be intentional about creating serendipitous moments.” Figma’s playful approach to collaboration influenced its recently-launched FigJam, a digital whiteboard that can help fill the need for serendipity.
Dylan speaks with the unique authority of a tech leader who has not only prioritized design but, with his team and products, greatly influenced it in a way that seems to have happened just in time for distributed collaboration.
“We’ve gone from a physical economy to a digital economy. I don’t think these are new trends or new things that happen but now, all of a sudden it happened all at once, and accelerated massively,” he says, echoing Matt’s May 2020 post Gradually, Then Suddenly.
“I think that we’re seeing every part of the economy shape around design,” says Dylan, noting how Figma has even observed collaboration in the product, beyond design, on days when other workplace chat tools were down.
Why does it matter? Because now, Dylan says, “Design leads to winning.”
Thank you to both of our guests for this latest episode of Distributed. We hope you enjoy it.
Congratulations to GitLab on its IPO earlier this week. You can read coverage of GitLab’s public offering at TechCrunch (GitLab’s mega IPO), Bloomberg, and plenty of other places.
In May, we interviewed CEO and Co-Founder Sid Sijbrandij on the Distributed Podcast. The conversation didn’t specifically cover a potential public offering beyond Sid acknowledging GitLab’s well-known aspirations to go public.
But the two CEOs focused on being public in great detail, especially in terms of GitLab’s well-documented transparency. In the conversation, Matt said, “…there are often CEO backchannels where you’ll ping another CEO and be like, so how does this work at your company or what do you do for this? And I would say that you are the one I ping. And 99.9 percent of the time it’s a link to your public handbook.”
Every company has a unique path to growth. Matt recently wrote about Automattic’s approach to fundraising and acquiring products, and this week TechCrunch covered our untraditional journey. Meanwhile, GitLab has carved out an unparalleled growth path, and this week is the culmination of years of effort and commitment.
Two things our companies have in common, inarguably, are a commitment to a fully distributed team, and passionate support of open source software — one of the most powerful ideas of our time.
We admire GitLab’s very transparent approach to both, and congratulate them for their listing this week.
“Every company has a poster on the wall,” says Matt Mullenweg in the latest episode of The Distributed Podcast. Matt welcomes Sid Sijbrandij, Co-founder and CEO of GitLab, another pioneering company with Open Source origins and a long-running commitment to a completely distributed workforce. Sid and Matt settle into a conversation about GitLab’s six values – which have been cut down from the original 13, and which are always visible in Sid’s video background – are reinforced in 20 ways at the fully-distributed company. GitLab, now with more than 1,300 employees, updated its values over 300 times in the last calendar year.
“They have to be reinforced,” says Sid, “and be alive in that way.”
And as for sharing just about everything publicly? “Transparency is sunlight.”
The values are part of the publicly-viewable GitLab Handbook that, with over 10,000 pages, details data both interesting and “mundane,” from compensation to how employees should interact with Hacker News. An example: “I think what’s really interesting is our engineering metrics. We pay very close to what we call the MR rate: how many merge requests did an engineer make over a month; how many did a team make over a month?” Sid shares. “If you push on that, people start making the changes that they make smaller to kind of increase that rate. The whole process becomes more efficient.”
Sid and Matt – an observer on GitLab’s board – get into the details: taking time off, leadership development programs, scheduling coffee chats that actually work, and much more. And they revisit predictions Sid made on Twitter in May, 2020, about the post-Pandemic future of distributed work. Check out the full episode above, or on your favorite podcasting platform.
500-page bound merger agreements, office printers, and libraries lined with law books. Legal work looks a lot different now that most in-house counsel (and law firms for that matter) have adopted some form of distributed work.
But that doesn’t mean the work itself has changed. Contracts still need to be written and signed, litigation still needs to happen, and employment law might be more important than ever. What’s become clear over a year into a global pandemic is that legal work can be even more effective without the office. To make it happen, however, lawyers need to adapt their communication mediums and technology in a way that fits company culture and mission.
Automattic’s General Counsel, Paul Sieminski, recently joined the Technically Legal podcast to talk about how legal work can thrive in a fully distributed company. “It’s aimed at a legal audience, and I love to remind my fellow layers how much value we can add to a distributed organization,” said Paul of his appearance on the podcast. “We are trained to communicate clearly, and especially to write cogently and persuasively. These are invaluable skills in any environment, but especially in an environment where writing is paramount…like a distributed company.” Paul has written on the topic in other places, such as Modern Counsel.
He talks about communication starting just after the 23:00 mark with host Chad Main. For that discussion, and legal topics spanning the advantages of creating a searchable document database, to what tools and protocols we use to communicate transparently while protecting confidentiality, you can learn more about legal work in the distributed model by listening to the full episode here.
“Was there a palpable time when you felt like…you had to have a new kind of thought as you got bigger?” asks Mike Maples Jr., host of the Starting Greatness podcast in an April conversation with Automattic founder and CEO Matt Mullenweg.
Matt shares several such pivotal moments in an episode full of stories and insight from the growth of Automattic, and of his own journey and leadership evolution.
“For better or worse, you become close personal friends with everyone because you’re kind of in the trenches,” Matt said, sharing a story about when the company almost accepted an acquisition offer at a time of friction among the small, but growing, Automattic team. “So when you fight, it kind of feels like you’re fighting with your partner, your significant other.”
Matt reflects on a journey from his Palm Pilot user group to first meeting Jeffrey Zeldman of A List Apart (and now a Principal Designer at Automattic), and later his first visit to San Francisco, all before committing full-time to WordPress and Automattic. Mike and Matt also touch on the difference between a learn-it-all and a know-it-all, and even some books that have been influential along the way.
Maples, partner in venture capital firm Floodgate, has also hosted Annie Duke, Mark Cuban, Tim Ferriss and David Sacks in the second season of Starting Greatness, a podcast dedicated to startup founders who want to go from “nothing to awesome, super fast.” You can listen to the full Starting Greatness episode, and all others, right here.
Join us for the latest episode of Distributed, as Matt Mullenweg interviews Jack Dorsey, co-founder and CEO of Twitter and Square. They discuss how both companies have embraced remote collaboration, the underrated value of deliberate work, and how questioning preconceived models from the get-go can change everything.
This spring, Jack Dorsey told Twitter and Square employees they could work from home forever if they choose. But a year earlier –– before the global pandemic happened –– he had already started working from home two days a week. There wasn’t the noise or the distraction. It was a place and a time where he felt more freedom and creativity.
Now, he reflects on how his way of working has evolved alongside Twitter and Square over the past year. From leading thousands of employees as a self-described introvert, to why he planned (and still does) to work from Africa for an extended period (spoiler: largely, to support entrepreneurs on the continent), Matt and Jack share ideas for combining the deliberate, thoughtful pace of asynchronous work with the serendipity that occurs in the office.
“If we can run the company without missing a beat,” says Dorsey of planning to work in Africa, “it really opens the door for a lot, especially our ability to hire anywhere as well.”
Tune in to learn how meetings work at fully distributed Twitter and Square, what open source and the punk scene have in common, why bringing thoughtfulness into collaboration is more important than ever, and if Jack Dorsey ever wants to go back to the old board meetings. Plus a whole lot more.
The full episode transcript is below. Thanks to Sriram Krishnan for help preparing for this episode.
For many, remote work is a recent phenomenon — a nascent practice brought about by public health concerns. By now, however, there are also quite a few companies that have used various distributed models for years, and the people who’ve been part of their journeys possess deep knowledge about what makes (and occasionally breaks) a fully distributed workforce.
Case in point: Sara Rosso, WordPress.com’s Director of Product Marketing. Sara recently celebrated her 10th anniversary at Automattic, and to mark the occasion she took to her own WordPress.com blog to share 10 leadership lessons she’s learned over the course of a decade working with and leading distributed teams.
Sara’s insights span a wide range — from ways to foster psychological safety in the absence of shared physical space, to tips on how to successfully separate work hours from personal time when they both take place in the same house (if not the same room). One of her standout lessons? Optimizing remote meetings to work for people with diverse communication styles and preferences:
Though written communication is a very strong skill needed in a remote company, there is likely a wide variance of personalities and work styles in the company. A remote company can attract both clear extroverts (like myself) and introverts who would be fine not to meet up even twice a year.
One of the ways I’ve had to learn how to lead team and project synchronous meetings is to be sensitive to all types of personalities. As Automattic has grown, it has gone from a company where I knew who had kids and where they each lived, to video calls with people whom I’d never met, never worked with, and in some cases I wasn’t even sure what country or city they’re sitting in.
As an extrovert I am especially aware I need to make space for others to contribute in a synchronous discussion. However not everyone wants to be included in that moment, especially when that means calling on someone spontaneously. Some of the advice I’d heard in the past for meetings was “call on people who haven’t spoken up” to make sure diverse voices are heard on the call. This is not a one-size-fits-all approach, and can definitely backfire.
Like any new employee, Scott Berkun had the jitters on his first day at Automattic. He was a little older than most of the people at the company, having spent the previous nine years at Microsoft. Although he witnessed firsthand the excitement of the tech giant’s glory days, office life was still rather conventional.
Now, in 2010, Scott was joining a young company with no offices, and — prior to his hiring — no managers. Before Scott joined, everyone in the company reported more or less directly to Automattic’s founder Matt Mullenweg and then-CEO Toni Schneider. Scott had been hired based on his own advice as an Automattic consultant. He had observed that the company had grown too large to operate efficiently with a flat structure. Scott suggested a turn toward a more conventional approach — the company needed hierarchy.
