Early thoughts on distributed work

I recently joined Automattic which is a fully distributed company. We have ~900 people (in all functions) working in ~70 countries, with no central office. We are one of the largest, if not the largest fully distributed company in the world.

I wanted to share some of my thoughts about the advantages and challenges of distributed work after two months – both strategically and from a practical implementation/execution perspective.

One very important principle about Automattic is we are set up to be a distributed company and all of our internal process is designed with distributed teams as the default state. This way, folks that are remote are not ‘2nd class citizens’ but are the core of the company.


  • Work from anywhere: Our people can live and work from wherever they want, which ultimately leads to happier employees that stick around longer.
  • Work when most productive: People can work when they feel most productive and manage energy, not time (one of my fave articles) taking into account their personal constraints (e.g. family) into their schedule. Managers, however, have a bit less flexibility.
  • Custom work environment: Some folks like others around, others prefer a quiet environment, others like to move around. At Automattic, people can set up their environment to suit their unique style which is very hard to achieve in a traditional office.
  • Everything is documented: We document everything using our internal blog system (called P2) and folks can always go back and find out the ‘why’ behind decisions. This is very powerful.


It’s worth noting that these are currently a set of initial observations for challenges, and I’m sure there are a number of good solutions to them which I’ll be actively thinking about as part of my work at Automattic. 

  • Onboarding as a new employee: Onboarding requires getting to know the right people (and building trust), learning the right systems, and developing the right judgment to know where to focus. Doing this remotely can be a struggle.
  • Building relationships: It’s easier to build bonds with people in person. Nuance is lost over Slack and Zoom and there is no substitute for time in person together. At Automattic, we have meetups to help build relationships but it increases the amount of time and ‘deliberate-ness’ required to get to know your colleagues.
  • Finding product-market fit: In the earliest stages of finding product-market fit, iteration can be slowed down because of async, documentation heavy nature of our work especially if vision is shared among different people. This is an area where I feel there are lots of areas for opportunity to improve with more frequent synchronous interactions. 
  • Changing direction: It’s much harder to get alignment and inspire towards a different strategic direction via text and video. It’s harder to recreate ‘energy’ and velocity in a distributed environment.
  • Separating signal from noise: We are a large team (900+ people) and there is a lot of content that is created daily.I’m spending about 15%+ of my day parsing through posts and comments to figure out what I should read, participate in, or make decisions on and as a new person it can be difficult to know where to focus. More experienced distributed workers have similar issues, but they are less pronounced, which shows that this is a somewhat learned skill.
  • Time zone management: It can be difficult to run teams across different time zones but there are also opportunities to increase velocity by folks working over a 24 hr period.

Joining Automattic

Sharing some personal news: I recently joined Automattic (makers of WordPress.com, Jetpack and WooCommerce) to help build better products for our customers. I’m very grateful to Kinsey and Matt for the opportunity.

Over the last few years, I’ve explored entrepreneurial projects and also invested full-time in early stage African technology companies. Throughout the exploration process, I realized that I missed building products and my motivation for investing was the desire to learn about new businesses and to support entrepreneurs in their journey.

I joined Automattic because the company was a great fit in a number of areas that I’m passionate about:

  • Empowering entrepreneurs with world-class tools: The cost of starting technology companies has come down dramatically and access to quality tools has improved dramatically. Entrepreneurs now have access to services to allow decentralized, asynchronous product development, open-sourced products they can build on top of, cheap hosting of content, and tools that allow a deep understanding of their data. These products typically have low entry costs that scale up as the businesses grow. This allows entrepreneurs all over the world to solve problems during their early stages without a lot of access to funding and without sacrificing quality. Automattic builds products to empower entrepreneurs.
  • Distributed work: I believe that talent is roughly evenly distributed, and enabling employees to work when they feel productive and choose where they want to live will allow companies both access to better talent and improve retention of talent. I’ve seen this firsthand through investing in tech companies in Africa that have distributed engineering teams with technical architects from abroad who collaborate with local engineering teams highly effectively. Automattic is fully distributed with ~900 people working in ~70 countries – check out https://distributed.blog/ (and Matt’s podcast) if you’d like to learn more about how we work.
  • Decentralization of creators: Creators all over the world are able to express themselves and find audiences that are interested in their content. They now have the tools to express their voice and discover, grow and engage their audiences. Bloggers are the new authors, YouTubers are the new tv producers and Podcasters are the new radio hosts. Automattic builds tools for creators.
  • Mobile-first internet users: There are billions of people in emerging markets who will experience the internet primarily through their mobile device, both as creators and as consumers. It’s a fundamentally different way of experiencing the internet compared to our reference points as adults in developed markets. There is a gap in high quality tools for mobile-first entrepreneurs and a significant opportunity to build these tools from first principles. Automattic is well placed to create this mobile experience.

I’m really looking forward to building products for entrepreneurs and creators all over the world at Automattic. 

Thanks for reading 🙂