This is an evolution of a prior post about remote work. Many are working remotely now, thanks to COVID-19. I’m assuming this will be more of A Thing™ going forward and decided to refresh my thoughts.

Enabling effective remote work is increasingly becoming a requirement successful tech companies. Hiring is competitive, costs of living are going up in tech hubs, and there’s an increased focused on cost and profitability in the markets.

The industry trends towards leaning into remote work and/or funding offices in less-expensive areas. For better or for worse, I have extensive experience working remotely or on distributed teams, both before joining Dropbox and then in bootstrapping Dropbox NYC over the five years I was there. Below are some of my learnings and thoughts.

Note that “remote workers” and “distributed teams” are very different things. Remote workers are physically alone day-to-day (often working from home), and distributed teams are groups of people working together in an office outside of headquarters. At this level of discussion, they’re similar enough that I’ll refer to both as “remote.”

What success looks like

Successful remote workers are:

• Motivated: they work on initiatives that are critical to the company’s success. Most of the canonical challenges from remote work (e.g. lack of promotion, feeling left out) are actually symptoms of not working on something that matters to the company. Giving remote workers mission-critical work is a forcing function to get the logistics right. As a side note, if a company isn’t willing to give critical work to remote workers, it shouldn’t explore doing remote work at all.
• Empowered: they’re able to act autonomously and make decisions within their scope. Decision making can be done locally without running everything through another person/team. This is especially important when there are timezone differences.
• Connected: they have the information they need to do their job. There’s no substitute for the nuance in real-life conversations and the hallway chats that inevitably happen, but the processes for making and communicating decisions don’t disadvantage those that aren’t there in person.

What success requires

Further leveraging remote work is certainly possible and potentially very fruitful, but a company must be thoughtful and deliberate about how to invest. Effectively taking advantage of remote work requires:

• Commitment: there must be a top-down mandate to fund important initiatives remotely, either as new investments or transferring existing important initiatives. The latter will move much faster than the former. It’s one thing to provide incentives or to encourage managers to look outside of their office for engineers, but attempts to move work outside of existing offices inevitably peter out when not accompanied by sustained top-down support.
• Focus: with remote work, it’s better to do fewer things well. A company needs to be strategic about which initiatives to fund remotely and focus efforts on those initiatives. It’s better for coherent organizational chunks to be remote than it is for every team to have a one-off remote worker. Remote work is hard, and limiting the number of teams that have to evolve their traditions and processes to accommodate remote work limits the risk of slowing down a significant portion of the company.
• Investment: while the long-term goal is cost savings, bootstrapping remote work is expensive, both in $$$ and in brain space. When building an office, it’s essential to invest in key people (site lead, early senior leaders) with frequent travel to headquarters and to accelerate hiring significantly by bringing in local recruiters that know the market . With remote workers, setting them up for success requires travel and in-person communication, especially if a team’s processes don’t already lend themselves to remote work. The greater the initial investment, the more likely a company is to achieve cost savings in the long term. A company must set expectations that costs will go down eventually, but not at first.

Remote as an office

Last year, Stripe announced Remote as an engineering hub. Rather than allowing teams to have one-off remote employees, they treat all remote engineers as being in the same “office.” In general, remote engineers work together, and the teams they’re on are entirely remote. I haven’t seen this in practice, but it’s an interesting idea. Remote workers already know how to work well with one another, the touchpoints with remote work that require high-bandwidth communication are limited to leadership, and the risks to slowing down every team that takes on a remote workers are minimized.