Coffee Shops, Office Space, and… the Future of Remote Work

Natalie Sandman

As a VC at Shasta Ventures, I look into technologies related to the “future of work” — automation/machine intelligence, collaboration/productivity, and much more. In this post, I’ll share thoughts on remote and distributed working.

I’ve always loved working in coffee shops. Maybe it’s the allure of being surrounded by people without having to talk to them. Maybe it’s the opportunity to strike up conversations with like-minded strangers. Maybe it’s just growing up in the Bay Area where people are on their laptops in public locations. More recently, I’ve been using time at coffee shops as a serendipitous way to learn more about remote work.


Remote work isn’t a new topic. Flash back to England in the late 1700s when manufacturing was done in people’s homes using basic tools machines — there was no central workspace and the lines between home and work were blurred. The Industrial Revolution then marked a shift to special-purpose machinery and mass production, moving work out of people’s homes and into the factories — a separation between work and home was created.

Fast forward to the late 90s when Office Space educated an entire generation on what work should not look like: daily trips to a gray, Kafka-like office where you co-worker keeps repeating, “Corporate accounts payable, Nina speaking. Just a moment.” For some workers, their companies expect them to be physically glued to their office chair from 9-to-5 (or much longer) all while being productive.

If you haven’t seen Office Space, go watch it now.

Jump to today’s workplace and there’s a wide range of what work looks like. Companies like Elastic pushed the envelope, choosing to go distributed from day one and proving that the fully-distributed model can work at public-company scale. Companies like IBM, chose to be partially distributed before defaulting back to a more traditional model of requiring employees in office, which caused major PR blows. More and more companies are finding balance in flexible work policies such as ‘Work from Home Wednesday’.

The combinations of anchored and remote workers within a company are infinite.

What’s Driving the Shift?

If remote work has been around for a while, what’s driving it’s resurgence?

  • Explosion of collaboration and productivity tech. Cloud-based technologies like Zoom, Slack, and JIRA are helping enable the communication — both synchronous and asynchronous, written and verbal — required to work remotely.
  • Workers increasingly demand flexibility. Whether they’re W2s or 1099s, workers increasingly value flexible schedules and the ability to work anytime, anywhere.
  • …and employers are responding. As workers demand more flexibility, employers are responding in order to retain talent in a competitive job market.
  • Companies are global from day one. The Internet has opened the door for companies to hire talent all over the world, not just within close proximity of their offices.
  • Workplaces optimizing for productivity not presence. Companies are increasingly less concerned with face time (perhaps a sign of today’s overwhelmingly digital world) and more focused on employee output. Allison Baum from Trinity Ventures wrote a great article on this.

Today’s Unanswered Questions

While remote work provides benefits to both employees and companies — flexibility, higher productivity, lower cost — the shift from a traditional workplace to an increasingly distributed one leaves a number of questions unanswered.

Specifically, how do we…

  • Mitigate loneliness when our workplace has historically given us community?
  • Curb procrastination when there’s no social-pressure to finish work?
  • Deliberately architect the way we work to support collaboration and foster clear, direct, open communication?
  • Build rapport and psychological safety without face-to-face conversations?
  • Ideate, make decisions, and execute quickly without in-person meetings?
  • Manage time zone complexity and operationalize HR logistics across global teams?
  • Hire people that will thrive in a remote work environment?

Looking to the Future

As remote work continues to become more common, we’ll see a number of changes:

  • Your “team” will look more like a tribe. It could include strangers, a cohort that meets periodically, or the actual people employed by your company. Regardless of who these people are, your “team” will be your accountability partners, un-blockers, and social community.
  • Technology will take the work out of collaboration and communication. Meeting notes will automatically be transcribed and decisions automatically documented. Physical interactions like huddling around a co-workers computer will be brought into the digital world.
  • The workplace will become more transparent, not less. Workers will know what projects their co-workers are working on at any given time and how this maps to company priorities. They’ll know whether it’s a good time to chat in real-time versus disrupting high-focus time like coding.
  • People will move to remote cities, countering urban crowding. Americans are flocking to U.S.’s most popular cities where there are more jobs and higher wages. As remote work becomes more common, people will move to locations where they enjoy the region’s activities and quality of life.

Up-and-coming Startups

Below are a handful of startups building products that help fuel remote workers:

  • Deel — helps you pay remote workers while staying compliant.
  • Disco — messaging-first kudos app to help your team celebrate culture and successes from anywhere.
  • Focusmate — distraction-free productivity tool where users can book virtual co-working sessions.
  • Loom — video-based communication that makes it easier for teams to share user-generated videos inside and across organizations
  • MURAL — digital workspaces for visual collaboration, inspiration and innovation anytime, anywhere, on any device.
  • Wisp — real-time collaboration for remote teams.

If you’re passionate about or building anything related to remote work, I’d love to chat! Send me an email at natalie@shastaventures.com — I’d love to hear from you.

Natalie Sandman

Written by

VC @shasta, ex-product @ravelinhq, @zenefits, @harvard alum. SF resident. Running on burpees and flat whites.

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