My new team at Automattic

Starting next week, I'll be shifting my focus at Automattic and joining our "WordPress Concierge" team.

It's a small group of talented folks who build custom WordPress sites for influential people and organizations across a bunch of different industries. I'll be creating and supporting the sites we work on while also helping to help the team scale up its internal tools and processes. I'm excited to flex a different mix of skills and ship some new kinds of things.

It's hard to believe that it's already been more than three years since I joined Automattic and began working with the VIP team, where I'm wrapping up my time this week. That role has been full of its own interesting and rewarding adventures that have taken me deep into the heart of the systems and tools that power the modern open web.

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Working for someone else

This week marks two full years of my employment at Automattic. I was fortunate to celebrate in person with a number of my colleagues as we hosted a workshop for our clients and partners in beautiful Napa, California.

People who know that I co-founded and built my own tech business before joining Automattic often ask me what it's like to work for someone else. My short answer is usually:

  • I miss some of the joys and challenges that go with being ultimately responsible for the success of a business venture...
  • ...but Automattic is a place where I am trusted with a level of autonomy that I'd be hard pressed to find in many other employment situations, and
  • I am mostly just enjoying discovering new ways of doing things and being a part of a bigger team with greater resources available for innovation.

This post is my longer answer. While working at another company it has been useful and interesting to notice what it's like to have a change in my professional identity, not be "the boss," enthusiastically support something I didn't create, and try to balance the joys of "employment" with the inner itch to again be a "founder."

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Distributed vs. In-Person Teams

TreehouseOne of the questions I get most since joining Automattic is about what it's like to go from working with a company where we were mostly collaborating in one office space in Indiana, to working with a fully distributed company, where everyone works from home, coffee shops, co-working spaces or similar spots around the world.

(The other main question I get is about what it's like to go from being "the boss" to working for someone else - a post for another time.)

The short answer: I'm appreciating and enjoying it, and I think it is the future of many kinds of work.

The longer answer follows.

The question of a distributed versus in-person setup for a team or company is discussed often in tech circles, perhaps even more so right now as tech companies face hiring challenges and consider related immigration policy issues. I feel like I've experienced both sides in some form now, having built and managed a web development firm for close to 17 years with a strong focus on working together in the same physical space (experimenting with remote workers along the way) and now having worked almost 8 months in a fully distributed configuration.

Going in to my new job, I was initially skeptical that I would find a distributed setup to be better than what I'd experienced working with my team in an office together. I thought it would be exciting, interesting and different, and despite all of the enthusiasm I'd built up for it (especially after reading The Year Without Pants: WordPress.com and the Future of Work) at some gut level I still suspected it would be a kind of nominally acceptable, second-best alternative to working with people in person. Continue reading Distributed vs. In-Person Teams

Automattic Grand Meetup Gratitude

It's only been about four months since I joined Automattic, but in that time I've had some great experiences working on amazing projects and websites with some delightful people. The past week took that adventure to new level as I joined my 270ish (and growing) co-workers for the annual company "grand meetup," held this year in Park City, Utah.

I wasn't quite sure what to expect going into the gathering; I'd been told that it would be overwhelming, chaotic, amazing, fun, productive, and lots of other things. I've of course spent time with co-workers before, been to a variety of tech conferences with intensive schedules, etc. but something about bringing everyone at a fully distributed company together for a rare chance to connect and collaborate felt different somehow - higher stakes and a little more scary. Flying across the country to spend a week in a remote mountain lodge with a bunch of people you met on the Internet...sounds a little intimidating, right?

A week later as I head home, I'm full of gratitude.

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I'm joining Automattic

wordpress-logo-stacked-rgbOne of the main reasons I get excited about Internet technologies is that they amplify the power of the written word and other kinds of creative publishing. Modern online tools enable bloggers, software developers, poets, journalists, novelists, chefs, filmmakers, marketers, photographers, artists, scientists, organizers and many other kinds of people to bring their creations to the world, at a constantly decreasing cost. And even through all of the cultural transformations we've seen spurred on by the Internet, the power of the written word remains - publishing can still change minds, start movements, spark connections, capture beauty, reshape lives.

Next week I'm joining Automattic, Inc., the company that makes WordPress, runs WordPress.com, and provides a bunch of other publishing-related tools and services. I'm joining the WordPress.com VIP team as a full-time VIP Wrangler, where I'll be helping to provide support, hosting, training, and other services to some of the biggest and best WordPress sites on the web (NY Times, TED, CNN, Time and more).

There are many reasons I'm excited about this, including:

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