Reflecting on 5 Years of Building Remote Culture

by Mark Faggiano June 19, 2018

A lot has changed about the way remote teams are perceived. When we started TaxJar 5 years ago, people overwhelmingly told us that remote work doesn’t scale. We were told time and again that eventually we’d need to get an office so everyone can be in the same physical location.  
As we celebrate 5 years (all without an office), we don’t hear from the haters as much anymore. What’s really exciting is we hear more from the new wave of remote companies that are determined to help shape the future of work.
Five years has taught us far more about remote work than can be captured in a single blog post. But in the spirit of trying to help the next generation of remote teams, here are our top learnings about building and nurturing the remote culture here at TaxJar.

What is ‘remote’ work anyway?

There are lots of definitions of ‘remote’ work and a variety of remote-like working environments. To us, remote work is not working from home a couple of days a week. It’s not working while travelling at a conference. And it is not working for a company who has both a physical location and employees who work from home.

We consider remote work to be working full time at home (or wherever you want) on a team that is also 100% remote (meaning the company does not have any physical offices).


Shared values = unlimited possibilities

One the most widely discussed benefits of being a remote company is worldwide access to talent. We’re fortunate to be able to hire the best people we can find no matter where they live. We can recruit talent from a diversity of locations, backgrounds, experience levels and culture, but there’s one thing we’ve noticed that our team all has in common: alignment of values. We’ve learned that when a team shares the same values, anything is possible.
This goes beyond core valuesOur team is aligned on things like…

  1. A desire to actually enjoy work…and to have hard work make an impact on the bottom line. So work that actually means something.
  2. Enjoying the people we work alongside every day. #nodrama
  3. Work isn’t everything. Families, hobbies, and other activities are all things that benefit from remote life.

At TaxJar, because we’re aligned we can focus on accomplishing our goal to make ecommerce easier for everyone.  Admittedly that’s a huge task, but it would be even more daunting if there were divides in the way people want to work and what role work plays in their lives. 

Reinvesting in People FTW

Since we’re remote, we’ve never paid a dollar in rent. That’s a big reason why we can run our business profitably. But stashing all that cash has to have a purpose. What we’ve realized is that the best way to spend that money is to invest in our team.
A low cost structure allows us to provide things like the very best medical benefits we can find, for example. Choosing a provider for benefits is an important decision, and at TaxJar we didn’t just want to check a box for healthcare, we wanted our employees to have one less thing to worry about. Life’s more stressful without adequate coverage.
Next, we value having face-to-face time as a team at least twice a year.  We proudly foot the bill for our entire team to gather for a week in cool locations like Boston, Austin and Santa Monica. This time is crucial for the team to be together and plan for the future.
At about 25 employees, we chose to invest in a hire to own our Employee Experience — someone whose only job is to focus on the team’s needs and make the employee experience better and more fulfilling. We can also invest in professional development, education on how to avoid burnout, provide incentives for folks to take time off, and show our appreciation with fun gifts to make working a little more enjoyable.
At first we did some of the above just because it was fun. But over time we’ve learned that purposeful investing in our team cultivates a culture of caring. When a company cares about their employees, the employees take care of that business. Besides it being the right thing to do, we’ve found that employees who feel cared for are a lot less likely to leave and are a lot more likely to refer their talented friends to come work with us.

Trust Before All Else

One obvious part of remote work is that there’s nobody watching you to make sure you get your work done. And that’s an important part of our culture.

We don’t care about the means by which someone at TaxJar gets their work done.

We don’t track hours or use time-tracking software. It’s just not worth the effort and it sends the wrong message.
We judge every employee’s productivity by consistently asking the following questions —

  1. Is the employee moving the needle for the company? Meaning, is the work they’re doing contributing directly to our goals?
  2. Do they deliver their work when they say they’re going to deliver? If someone promises a deliverable by a certain date, we expect to see that work on that date. If it’s not going to be done on time, we expect to hear about it a lot sooner than the due date in a team standup.
  3. Are they living our core values?

If the answer is ‘yes’ to all of those questions, then we’ve hired the right person. If there’s a ‘no’ in one or, gulp, more of those questions then we’ve made a mistake.
We’ve learned to trust our team until they give a reason why we should not. If we cannot trust a person enough to keep them on the team, it simply isn’t going to work out.  
We’ve learned that teams are happier when they are trusted to perform to their goals. Nobody wants to be watched over their shoulder. Our culture depends deeply on each one of us trusting each other in order to deliver what we promise. If trust is lost, then a key part of our culture breaks down.


Times are changing as remote companies are becoming more common. There are a lot of unique challenges to building a remote culture. We’ve found that if you have trust, align the team on values, and prove to your team that you care then your chances for success are greatly enhanced.
What are your biggest learnings as a remote company? Where do you think remote work is headed in the next 5 years? Let’s discuss in the comment section below.

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