The Benefits —

of and Questions Facing Remote and Distributed Startups


Now that it’s easier than ever to assemble teams of talented people across the world—without having to even share an office—what are some of the benefits and challenges faced by these technologically-enabled work arrangements?

The new normal

In 2013, Scott Berkun authored a book called The Year Without Pants in which he shared his experience working remotely for WordPress. Since then, these non-traditional work arrangements have become the norm at many companies. They are categorised within 3 broad groups:


  • Fully Distributed: Where team members rarely come into the office and work almost exclusively through the Internet, such as WordPress when it first started.


  • Semi-Distributed: Where some of the roles such as leadership or management are staffed at a headquarters that manage distributed team or teams (Hashicorp, Mattermost).


  • Small Offices: Often new offices can be created to start and host functional teams such as support or sales development.

The challenges

While versatile, there are certainly challenges with having an arrangement like this. This includes ensuring good communication strategies across geographies, especially in cases where the team is distributed. In addition, it’s important to share valuable knowledge or decisions made in person by one part of the team across the network. Finally, the largest challenges can sometimes center around hiring and compensating contractors and employees in these teams, especially ensuring that a company’s practices comply with local laws.

Speaking from experience

While technology and global connectivity have made previously unheard of work arrangements possible, the versatility for both the company and the individuals involved (who often enjoy flexible schedules) does come at a price. For distributed teams in creative companies especially, one of the biggest challenges is creating and maintaining a passionate work culture despite a lack of in-person face time with which to exchange ideas on the fly.


What’s more is where dedicated operational personnel is lacking, this chemistry and synergy needs to be maintained through reliable systems that can account for complex detail-oriented creative work. This doesn’t just mean individual programs (such as if a team is sharing an Adobe CC license) but how the myriad of programs in a team’s chosen tech stack play together. In short, for these distributed creative companies to thrive, they must properly use location-freeing technologies. The tech must have limited energy-sapping snags to keep creative juices flowing.


– Nate Kan