Manzoor and his wife were expecting their first child near the end of July, but the pregnancy became complicated much earlier. “During the sixth month, we started experiencing problems, having frequent hospital visits,” he said. “Automattic was very supportive and our team lead was as well.” 

A family in crisis

At 32 weeks, the situation became urgent, and Manzoor’s wife had to undergo an emergency C-section on June 6. Their son was born weighing 1.4 kilograms—“a tiny creature,” in Manzoor’s words.

In the weeks and months that followed, his care required close attention and constant effort at home. Manzoor said he and his wife alternated “skin to skin” care, and because the baby was too weak to nurse, they had to feed him by spoon for four months. Fortunately, “since I had the parental leave, I could focus completely on my wife and child,” he said.

Support when it’s most needed

That time away from work made an immediate difference. “I had to start my parental leave immediately, so I dropped a note to my HR wrangler,” Manzoor said. “A huge burden lifted off my chest. I could take care of my wife.” He described the relief in simple terms: “Not caring about my work during those days was a huge relief.”

The support extended beyond schedule flexibility. Because his leave was fully paid, he said the family did not have to take on another source of stress while caring for their son. That stability helped Manzoor stay present through his wife’s recovery and the long routine of feeding and monitoring a premature newborn.

He also remembered the practical care that filled those months. “I could cook for my wife without any time constraints and make sure that she recovered and wasn’t getting stressed by all the hassle we went through,” he said. By the end of three months, his baby’s weight had reached three kilograms, and Manzoor returned to work. 

Automattic provides six months of parental leave, so Manzoor was able to split his leave in two sections, giving him the flexibility he needed to take care of his family: “Then at six months I went on three more months of parental leave, and we had a vacation with my wife, the baby, and my parents.”

Real families, real life

Stories like Manzoor’s show how leave policies affect real families in real moments, especially when life does not follow a plan. In this case, paid time away from work created room for care, recovery, and financial stability during a medical crisis that began months before the baby’s due date. It also offered something harder to measure but easy to understand: peace of mind.

Learn more about Automattic’s employee benefits. And if our mission appeals to you, check out our open jobs and consider joining us.

Earlier this year, Automattic brought 54 employees to New York City for two weeks of intensive AI training. Two full weeks of hands-on building, experimenting, and rethinking what’s possible when AI becomes a core tool in how we work.

Why This Matters Beyond Automattic

Automattic is the largest contributor to the open source WordPress project. We invest significant human time and resources into its development, security, and growth. When we train our people on new capabilities, those capabilities show up in our contributions. The tools our teams build, the problems they learn to solve, the workflows they develop—all of that feeds back into the WordPress ecosystem.

What We Did

The training was hands-on. Participants built these real projects in two weeks:

• AI-powered chatbots tailored to specific WordPress publications
• Content workflows that summarize, draft, and adapt material in a publication’s voice
• Automated triage systems that parse bug reports, spin up test environments, and surface findings—turning hours of maintenance into minutes
• Plugins optimized for AI agents, making WordPress content more accessible to AI-powered discovery

Attendees learned how to tame context windows and provide supporting skills, workflows and agents to the AI tools. These are working tools, many already in use or publicly available. 

The Bigger Shift: Who Gets to Build

AI is collapsing the distance between idea and implementation. People who’ve spent careers working around technical constraints—marketers, editors, support specialists, project managers—are now building functional tools themselves. At Automattic, this means more of our team can contribute technically to the products and projects we support. 

This democratization of coding means I’m not limited by my coding skills; I’ve got superpowers to create custom solutions and make WordPress even better. For the broader WordPress community, the implications are similar:

• More people can build: Plugin development, site customization, and workflow automation become accessible to people without traditional developer backgrounds.
• Iteration accelerates: Ideas move from concept to working prototype in hours.
• Contributions multiply: When building gets easier, more people contribute—to their own sites, to clients, and to open source.

This is the kind of work that becomes possible when a company invests in AI fluency at scale. Success heavily depends on a clear vision, architectural consistency and radical quality control. AI doesn’t absolve responsibility, though. The contributor is responsible for the code, the implementation, unit tests, and the documentation. 

Preparing for the Third Audience

One project from the training points to where the web is heading. Inspired by Dries Buytaert’s concept of “The Third Audience,” participants built plugins that serve Markdown versions of content to AI crawlers—optimizing for humans, search engines, and the AI agents increasingly mediating how people discover information.

As AI-powered search and assistants become more prevalent, making your content easily digestible for these tools could become as important as SEO once was. I started a plugin to replicate this for WordPress. The first version of the POC is available on GitHub. The next step is to spruce it up and submit it to the WordPress repository. 

Bringing AI to the Broader Community

Investment in AI literacy extends beyond Automattic. Through a donation to the WordPress Foundation and University of Illinois Chicago (UIC), Automattic has enabled the launch of the nation’s first workforce-focused AI literacy curriculum, developed in partnership with the UIC Tech Solutions Open Source Fund. The program, called AI Leaders, is designed as a workforce-first credential, teaching AI literacy through hands-on execution.

Automattic is also bringing these conversations into the broader tech community. Through our New York City space, we host dev/ai/nyc, a monthly AI meetup open to developers, designers, and digital professionals. We have also sponsored the EvolveDigital Summit in New York City, where we led a workshop on using AI to create, publish, and grow audience engagement through WordPress.

What This Signals

Flying dozens of people across the country for two weeks is a significant investment. It’s also a statement about our priorities: We believe AI fluency is essential for the people building and supporting the products and projects that power the WordPress ecosystem.

For me, what comes next is exploring whether Claude and I can contribute to Playground and Gutenberg to resolve some minor issues, and ongoing contributions to WordPress core. 

The web is changing. The companies that thrive in five years will be the ones that learned to build with AI now. This two-week training turbo-charged everyone’s AI proficiency and increased their outcome five to 10 times bigger, faster, and better. 

Links to learn more:

• How to Build WordPress Plugins with AI: Claude Code + WordPress Studio Setup Guide
• Build WordPress Sites with AI: New Plugin and Skills for Claude Cowork
• It’s official: WordPress.com has a Claude Connector
• Connect AI Agents to WordPress.com with OAuth 2.1 and MCP

Less is more

You might imagine that as a fully distributed, remote-first, remote-last, remote-always company, Automattic must keep its people constantly stuck in Zoom meetings, but the truth is the opposite. Relying instead on asynchronous, written communication—via Slack, Linear, and our own P2 platform—enables us to work with best-in-class partners wherever in the world they choose to be located. No worries about time zone differences. No hours spent on discussions we can take care of in a few minutes of writing. More time to think and create, less time spent blinking into computer cameras. Sounds good, right?

Here, care of our CEO Matt Mullenweg, are the questions we ask ourselves before agreeing to any synchronous meeting:

1. Am I investing time toward the things that are doing the most to help me grow and improve my ability to contribute?
2. How much of my time is contributing to my team’s goals, and choosing the right ones?
3. Is the work effective? Is it moving the needle? Can I describe it to a friend over dinner in a way that gets them excited? Can I blog about it?
4. Are all my meetings so effective that I look forward to them? (Don’t laugh. It is possible.)

One life to live

Synchronous time in a distributed organization is precious—even sacred. And while we spend it generously when onboarding new employees, we maintain a better work/life balance—and healthier, more productive mental attitudes—by keeping inessential meetings to a minimum. If you’d rather work than sit through endless conversations, we may just be the place for you.

For more about Automattic, visit our website. (Hint: You’re soaking in it.) And while you’re here, check out our 20 year timeline. If you like what you see, consider working with us. Our open jobs are some of the most exciting in open source and tech, and our benefits and pay are pretty sweet, too.

On July 16, we invited friends and media to our Automattic Space in NYC’s NoHo to celebrate Beeper’s major new update. CEO Matt Mullenweg shared his thoughts on how Beeper’s powerful open source solution—which brings all your conversations from various platforms into a single, secure app—fits alongside Automattic’s long-term vision of democratizing publishing, ecommerce, and messaging. Beeper CEO Kishan Bagaria closed out the presentation by walking us through the app’s new features, followed by a night of music from DJ FaltyDL and locally sourced snacks. 

Sharing a great evening with friends is the original group chat, and made for a perfect way to kick off the next chapter of Beeper. We can’t wait for you to try it. Download it now, and experience the event through the gallery below.

On June 20, 2005, Matt Mullenweg made his first hire: Donncha Ó Caoimh, a software developer who had been working on the WordPress project. And with that, Automattic was born.

By the following summer, the company was nearly 10 people strong, and brought its employees together for the first Grand Meetup. The meetup may not have been grand—Matt picked up attendees at the San Francisco airport, and they experienced a small earthquake—but its ambitions certainly were. What began with the bold idea that publishing should be free and open has evolved into a fully distributed software company that powers tens of millions of sites, stores, and conversations worldwide. As Matt himself put it when commemorating 10 years, “We began building a business which looks remarkably similar to what Automattic does today. (We’re all still at Automattic, by the way.)”

In the Beginning

In 2004, Matt left his native Houston to work at CNET in San Francisco; that same year, Donncha merged his project, B2++, into the WordPress codebase. Their goal in joining forces was to make a version of WordPress that anyone could start with.

After Automattic’s birth, things moved quickly. In September 2005, Matt shared that WordPress.com reached 100 blogs—and then, in short order, 1,000. The next month, Matt left CNET to concentrate on WordPress.com full time. The anti-spam tool Akismet launched soon after, and Automattic began expanding its roster of products and services at a steady rhythm. The foundation was already in place.

Building a Different Kind of Company

In 2010, Matt wrote the Automattic Creed, a set of guiding principles that still shape how we work today. He opted for a fully remote company—a bold move at the time (and even today!).

From the start, Automattic emphasized transparency. We de-emphasized traditional email in favor of P2, using our internal blogging tool to make ideas visible and knowledge shareable. As Matt said on Distributed.blog, “There was all this intelligence and data and wisdom being lost in people’s inboxes. . . . The key for us was transparency.”

Distributed but not Distant

We’re a fully distributed company, but we know the magic that happens in person. That’s why meetups are central to our culture.

That first Grand Meetup in 2006 included the company’s earliest employees: Matt, Donncha, Andy Skelton, Ryan Boren, Mark Riley, and Toni Schneider (who would become Automattic’s first CEO). By 2013, Grand Meetups had evolved into week-long gatherings with hundreds of Automatticians from all over the globe, featuring flash talks, hackathons, meals, and memories that still shape how we work together today. As Automattic grew, meetups of all sizes became integral to the company; on any given week of the year, various teams gather at locations around the world. From close-knit team offsites to company-wide Grand Meetups, these events are marked in all our calendars. 

Our Mission: Democratizing the Web

A healthy company can’t succeed on vibes alone; for anything to work, a shared mission has to underpin every decision, every product, and every person. 

Our mission has always been to democratize publishing, commerce, and messaging. (Well, it was originally to democratize publishing, but Woo’s arrival in 2015 and Beeper’s in 2024 helped expand that vision.) What that looks like in action is investing in products and services that make your life better. It’s building a suite of tools that help anyone, anywhere, share ideas, build businesses, and communicate freely, regardless of their income, language, or beliefs.

Publishing

We began with WordPress.com, and over time, developed software that improved collaboration and connection across the web. In 2007, we acquired Gravatar, a digital passport for the web. We’ve expanded since then to include WordPress VIP for enterprise clients—like Salesforce, Time.com, NewsCorp, and the White House—and Newspack to help newsrooms thrive. We also have Day One, Pocket Casts, and Tumblr, as well as award-winning publications The Atavist and Longreads. While the media landscape has undergone seismic changes over the past 20 years, we continue to uphold the highest standards of journalism and storytelling.

Commerce

As we grew, it became clear that people were doing more with their websites, so creating economic opportunities worldwide became a crucial pillar for our business. WooCommerce started as a simple plugin and a simple idea: What if anyone could turn their WordPress site into an online store? Since 2015, Woo has transformed into the world’s most popular ecommerce platform—still open source, customizable, and helping millions of entrepreneurs sell anything, anywhere. 

Messaging

Over the past two years, we acquired Texts.com and Beeper, merging the two to build a bridge across the walled gardens of messaging. We believe communication should be accessible, encrypted, and open. We also recently acquired Clay, a relationship management tool that automatically organizes and intelligently searches your entire network. 

Today

As of 2025:

• WordPress powers over 43% of the web.
• WooCommerce is the world’s leading ecommerce platform.
• We’re more than 1,480 Automatticians in 82 countries speaking 110 languages.
• Our product suite includes WordPress.com, WooCommerce, Tumblr, Simplenote, Jetpack, Longreads, Day One, Pocket Casts, Clay, and more.
• Just this year, we’ve launched innovations like the AI Website Builder and the 100 Year Domain—with more to come.
  

What Ties It All Together?

A belief in the open web.
A commitment to user freedom.
And the idea that great software should serve people—not the other way around.

To every publisher, builder, developer, and dreamer who’s been part of our journey: Thank you. We’re just getting started.

Here’s to the next 20.

—The Automattic Team

In the US, June means Pride Month—and those of us in Queeromattic, Automattic’s LGBTQ+ resource group, want to share an update about our recent efforts at the company. 

First, however, we also want to say that we’re still here and we’re still queer. That might seem obvious, but as more and more states introduce legislation that constrains our lives and liberties, it also feels important to say.

We’ve again renewed our longstanding partnership with Out in Tech. This will be our eighth year of collaboration, and we’ll continue to build upon the 35 hackathons we’ve co-sponsored and 250+ WordPress.com sites we’ve built for various nonprofits all over the world. Please join us at future events, and consider supporting Out in Tech; they work tirelessly to help 70,000+ LGBTQ+ members advance their careers, grow their networks, and leverage tech for social change. 

We’re also joining the new Open Horizons Scholarship, along with a few of our fellow resource groups. Each group is contributing $6,000 to the endowment, which is currently at $30,000 and counting. Queeromatticians will help select recipients and provide in-person support at WordCamps for LGBTQ+ scholarship recipients. We’re especially excited to work alongside other Automattic Resource Groups to build on last year’s LGBTQ+ empowerment grant and welcome more underrepresented contributors to the WordPress community.

Finally, we’re repeating the Share Your Pride photo drive, complete with some cash prizes for selected winners. Representation matters, and we want the WordPress Photo Directory to have strong rainbow-themed options for anyone blogging about Pride this month—or sharing about their LGBTQ+ness anytime. 

Queeromattic was the company’s very first resource group, and we remain steadfast in our mission: advocating for our fellow LGBTQ+ employees, sharing support through social calls and private Slack channels, and proudly sharing who we are in our work. We know that concrete measures matter more than empty statements, and we’re excited to keep focusing on the work at hand. Happy Pride—and Happy WordPress-ing!

It’s been 10 years since a single question tore the internet in two: blue and black or white and gold? We’re talking, of course, about The Dress.

On February 26, 2015, a poorly lit photograph of an ambiguously hued, two-toned lace dress left social media in tatters. Was it blue and black? Gold and white? Scientists have since confirmed it’s the former, but at the time—and even now—millions swore otherwise. 

Unlike so many viral memes with cloudy origins, we know exactly who to thank for this one: Automattic’s very own Cates Holderness.

Cates, now editorial and marketing lead at Tumblr, was responsible for one of the biggest viral moments ever—even if the book may never fully close on those colors.

Let’s go back to that fateful day. Cates, then the community manager at BuzzFeed who was running the brand’s Tumblr account, received a Tumblr message and a corresponding post containing the now-infamous photo. Caitlin McNeill, a Scottish musician, had performed at a family friend’s wedding where the photo—taken by the bride’s mother—first made the rounds. “Some people see it blue, some see it white,” she wrote. “We are goING CRAZY.”

Cates showed the Tumblr post to her coworkers at BuzzFeed’s New York office. She saw blue and black, but others saw white and gold. Within minutes, a crowd had formed at her desk. 

As you know by now, this was just the beginning.

Cates reposted McNeill’s query onto her own Tumblr and X (then Twitter, RIP), and created a BuzzFeed poll titled “What Colors Are This Dress?” Before leaving work, the Tumblr post had 5,000 notes. When she emerged from the subway in Brooklyn and regained internet access, her phone crashed from the deluge of notifications. There would be more than 7.6 million tweets, and the poll would be seen by more than 38 million people. The Dress had gone viral.

The debate raged for months. On Twitter, Kim Kardashian and Taylor Swift weighed in, with hashtags like #whiteandgold, #blueandblack, and #dressgate dominating the platform. Serious media outlets analyzed the optical illusion and what it said about visual perception, making it nearly impossible to escape. If there were a Criterion Collection for memes, The Dress would arguably be Citizen Kane—or, at the very least, The Devil Wears Prada.

A decade later, the legacy continues. The Dress has an extensive Wikipedia page, which appears at the top of the Google results for the phrase “the dress.” Cates was recently a Pop Culture Jeopardy! clue, and even appeared on The Today Show last week in honor of the milestone. 

The Dress now stands as the (white and) gold standard for internet memes. Even today, trends are measured against it. Is Holding Space as big as The Dress? What about The Rizzler? The answer is usually no, but only time will tell.

The Dress also represents a relic of a bygone internet: It was one of the last moments that captivated every online platform and every demographic at once, all in a matter of hours. In today’s fractured digital landscape, it’s hard not to be nostalgic about a meme taking over just like that, amusing and perhaps enraging us, and then fading away—no short-lived celebrities, deep discourse, or anything remotely close to a “Dress-coin” involved.

To celebrate the big Dressiversary, Cates reflected on the moment’s impact and lasting relevance. Watch our exclusive video interview above, and long live The Dress!

Nicola Hodd knows that parenting while working can be extraordinarily challenging. She also knows it doesn’t have to be. Nicola, a marketing operations wrangler for Automattic’s WooCommerce business unit, shares her experience of returning to work after maternity leave two years ago, when her child was just starting daycare: 

“Those first few months, especially, were quite hard to adjust to working life again, and juggle the schedule with a little one,” Nicola said. “And not only that, but he joined daycare in the winter, and just caught every bug that seemed to be going.”

Benefits not only a mother could love

What made this transition manageable was Automattic’s exceptional flexibility. Nicola could work from home, attend video calls with her child present when needed, and adjust her working hours to coordinate childcare with her partner. She adds that these benefits “might not be absolutely groundbreaking, but they really do make a massive difference to my life, being a mother of one child.” 

Nicola emphasizes that this level of understanding and flexibility is still relatively uncommon in the UK workplace culture.

“To have a bit of flexibility was just, yeah, it was just amazing, really, that if he needed to be home, I could sit there on calls with him there with me,” she said. “You know, none of my team minded at all. They totally understood.” As time progressed and they settled into a routine, this flexibility continued to prove invaluable.

Additionally, working from home frees Nicola to participate in her child’s daycare activities, such as holiday parties, and respond quickly to any needs that arise. Nicola reflects that without all this flexibility, she might have had to reconsider her career aspirations, as she couldn’t imagine managing a rigid office schedule with a long commute into central London while being a parent.

“So I think, as good as employers are getting nowadays, Automattic just stands out,” she said. 

This equality helps reduce the common concern that taking time off for childcare might disproportionately impact women’s careers. 

No penalty for parenting

Notably, Nicola highlights another significant aspect of Automattic’s culture: the normalization of parental leave for both mothers and fathers. This equality helps reduce the common concern that taking time off for childcare might disproportionately impact women’s careers.

“It puts less of an onus on the women feeling like it’s like their career that’s being jeopardized because they need to take time out for their children or, you know, they’re taking leave because they’ve got a new child coming. I love the fact that it’s very equal here, and actually everybody is used to just covering for somebody being on leave. I think that changes the perception of women a bit, like not being as worried about taking time out—because actually a lot of people take time out here for different reasons.”

Nicola appreciates that the company treats many different types of leave—whether for parental responsibilities or sabbaticals—as a normal part of work life, with established systems for coverage during absences.

Work-life balance is more than corporate jargon

While Nicola acknowledges that her story might not appear “groundbreaking,” she emphasizes its importance precisely because it represents an ordinary experience that significantly impacts many families’ lives.

She notes that while some people choose not to have children, others make this decision due to workplace constraints rather than personal preference, underlining the importance of more employers adopting flexible policies like Automattic’s.

“A lot of people are choosing not to have children nowadays because it is so hard to juggle everything,” she said. “And if that’s a choice, that’s fine. But I think it’s hard when the choice is made up for you because of the circumstances and not because that’s what you chose to do. So, yeah, I think it’s very important. Employers need to be more like Automattic in general. Automattic raises the bar high, that’s for sure.”

Help us keep raising the bar

Our thanks to Nicola for sharing her story.

The humans of Automattic make the web a better place by creating experiences for more than a billion people each month through our work on WordPress.com, WooCommerce, Tumblr, Jetpack, Pocket Casts, Day One, and many other products. If Automattic’s unique work culture and mission to democratize publishing, commerce, and communications interests you,  join us!