EVERYBODY WINS: How to Build an Irresistible Culture for a Fully Remote Team

An Interview with TaxJar’s Darcy Boles

For years, the idea of working from a space as comfortable as your own living room was only a hazy dream for most American workers. Leaving the creature comforts of one’s home or chosen space for the formal realm of an office seemed like it was part of the deal with a working life, as if a numbing commute, fluorescent bulbs, and second-rate coffee were parts of the daily conditioning a worker needed to be tamed into running with the pack at work. The reality of modern working in America, however, has revealed that working remotely is not only enticing for the individual employee but also an enriching way to elevate a company’s culture.

Darcy Boles, Head of Employee Experience at TaxJar, the fully-remote SaaS company that helps businesses automate their sales tax calculations and filing, knows a thing or two about the benefits of remote work:

“I came from a tech company that covered all my lunches. We had goat yoga, we had everything under the sun. It was absurd. But I didn’t want that. I wanted my life, and I missed going to the coffee shop. I missed interactions with my community. I was always at this office all the time. Remote work opens up this world where everybody wins.”

Darcy Boles alongside her team and her dog, Blanche at JarFest 2020 in Savannah, GA

Boles’ journey in the workplace began in the hospitality industry, where she discovered she “had a huge heart for working among human beings.”

“About seven years ago, I found Airbnb when there were about 600 employees, and I left four years later at almost 8000 employees. That’s huge growth. It was there I realized how much I loved teamwork and building things from nothing. I love creating experiences for people.”

That said, the demands of getting to and from the job – as opposed to any stressors of the job itself – led Boles to her eventual misgivings. “Airbnb has offices all over the world, and I wasn’t permitted to work remotely, so I was flying to San Francisco ten days a month for over a year, and it was taxing on me,  and my dog who was flying with me. I was happy with the work I was doing, but I couldn’t do it in an environment where I could really thrive, especially when thinking about the fact we have technology to do all this. I couldn’t do it anymore.”

There weren’t a lot of social events and not a lot of people that wanted to connect on a business level. I lived in this tiny little mountain community that was snowed-in most of the time, so how could I feed my creativity and also build something as a team that was really meaningful?”

That’s when Boles heard about TaxJar. “I realized this is what people are doing, working remotely. I didn’t have to give up my lifestyle. You strip all the rules away from an office, but you keep the ethics, the morals and the goals.”

It’s no longer far from the norm to hear that someone is navigating a successful career from their home or from public shared spaces, and often on their own schedule. Businesses are discovering quickly that the old nine-to-five, in-office model assures little beyond consistent attendance during the requisite hours, while a remote working model encourages the fostering of a superior workforce, with fewer restrictions on physical locations and time zones and more focus on getting the best employees for the job.

TaxJar team members at JarFest 2019 in Nashville, TN

Even more surprisingly, perhaps, are the ways in which some companies based on remote workforces are able to still engender a rich culture of like-minded coworkers and mission-driven success.

TaxJar, which is made up of a 100% remote team, is the perfect example of a modern company that has mastered the craft of creating an irresistible culture for its remote workforce.

Asked to describe the company’s core values in a few words, Boles says:

• “The first one is fostering a team built on trust. We’re an incredibly transparent culture. I think you have to be in remote culture, just to eliminate fear and our own imposter syndromes. Mark shares our financials across the company to every single person, down to the cent. Knowing where we stand and where we’re going together as a team is huge.”

“Trust – to have a remote company you need to trust your teammates, and it’s apparent that our team trusts one another to get our work done.”

• “We’re proud to be 100% remote. We’ve been fully remote since the day we opened our figurative doors seven years ago. It’s taken successes, setbacks, and some truly remarkable teamwork to glean the knowledge we have. We have many different backgrounds and lifestyles, and we believe that a diverse team can create better solutions for our customers.

• “Another word is meaningful. One year for our company holiday gift, we gave everybody footie pj’s. We called them ‘TJ Pjs’, and they were bright green with the TaxJar logo. That spawned from a conversation on our sales channel where two of our salespeople were joking, ‘I’ll buy you pj’s if you can actually do all 10 deals you’re trying to get done today in your pjs – and he did! So there’s always a meaning behind how we build our culture.”
• “We’re in control of our own destiny, not only as a team by not being limited to raising additional funding, but as individuals having the autonomy to work when and where it works for us. The sky is the limit to making our dreams become reality when the chains of an office are removed.”

“Being remote, the diversity of our backgrounds is mind-blowing. For example, our team is made up of parents and those who are child-free – they aren’t the same life experiences, but everyone celebrates each other. We have teammates who live on boats and in RV’s, those who are rural and urban city dwellers, then everything in-between… They’re remote for a reason. But we’re tied by our values, which makes it so special,” Boles says.

TaxJar team members at JarFest 2019 in Nashville, TN

“This is a true team environment, where everyone’s opinion is valued and appreciated. We value diversity in all forms and strive to give everyone the chance to design their work and schedule.”

It seems almost quaint in 2020 to think how much of the history of working in America is tied to the 9-to-5 model when we consider how large and diversified the country really is. Since we’ve all long since been forever connected by what used to be called the“information superhighway,” the idea of harvesting a staff from just the area surrounding a central office location by twenty or thirty miles seems hopelessly self-limiting.

In a country as big as the U.S., we’re diversified not just by heritage or by regional twang, but also by ways of thinking that are organically tied to each type of landscape we encounter as we survey the fifty states. If you have a good enough idea to go out on the limb and start a business, you want the best minds in the nation and not just the neighborhood.

As far as building a culture among people who will only see each other a few times a year, “It doesn’t just organically happen,” Boles says. “In a remote culture, you can’t just assume that somebody is going to run into somebody at the coffee stand. A water cooler doesn’t exist. So you can’t expect people to connect without some sort of platform. There’s a lot of intention that goes into the inclusivity of building these connections.” By creating social channels like “Plant-based at TaxJar”, “Travelin’”, and “Health and Wellness” on their main communications platform, Basecamp, TaxJar has fostered an environment where employees can make authentic connections outside of their work-related projects.

Boles told us about some of the triumphs and mild tribulations TaxJar faced on the road to crafting an award-winning remote workforce culture. Among the major successes in terms of scaling the culture:

• “Always sticking to our values. Any big decision that conflicts with our big core values, we wouldn’t do it. I say that with utmost confidence.”
• “We’ve hired right. It’s really easy to get addicted to hiring as you scale and to try to put a body in the seat because you need the work to get done. What we’ve done really well not wavering in spending four to six weeks on a candidate, making sure we’re getting the right fit for us and our candidate.” TaxJar’s hiring process is methodically designed to ensure they hire employees who will not only excel at the job at hand, but bring a skillset that will teach the rest of the team along the way. This process includes a mutual trial period, where candidates spend dedicated time working on projects and interacting with their potential team. “We go out of our way to make sure a candidate has the opportunity to really get to know individuals on the team, and the culture of our company.”
• “We’ve also continued with our company off-sites, which we call JarFests. Having a twice a year in-person connection is magical. Because we work so autonomously, you don’t have the opportunity for those regular personal encounters, and then you get together and there’s this magical feeling. One of our goals for JarFest is to capture that same feeling no matter how many people are in the room, and we’ve done that.” JarFest was created to promote connectivity across a remote team by allowing everyone to get to know one another on a deeper level. At JarFest, our team is able to present new projects and share ideas for driving our business forward. This connection invigorates us for the next 6 months until we meet in person again.”

TaxJar team members at JarFest 2020 in Savannah, GA

As far as pitfalls the company faced along the way, Boles offers these:

• “One of the dangers of remote work, and I struggle with this, it’s very easy to overwork yourself, and feel you have to prove yourself because you work remote. That comes from our bruises in the past, from maybe more traditional office work. You have to be very conscious of setting those boundaries. Leadership has to model that. The team feels more comfortable taking time off if I take time off, and that’s really important to me.” Boles has learned to embody this mentality by notifying her team whenever she’s going to catch the morning surf and other team members have translated that to permission to play, enjoy and schedule their day around the things that mean the most to them.
• “When you scale 100 people in one calendar year as we did, there’s a lot of catchup you have to do. 2019 for us was about ‘the team we need,’ 2020 is going to be about ‘the team we have.’ So now we have to ask ourselves how we switch gears from getting everyone ramped up to sustaining the culture and working on professional development? How do we continue to break the mold and also keep this way of remote life for our employees, who now have their feet in the figurative door? Let’s get that other foot and run ahead.
• “Another mistake I’ve seen other companies make, including us, is that when you start a company and you’ve got maybe 25 or 50 employees, you don’t necessarily think about the scalability of the software you might be using. For instance, we’re currently switching over from an applicant tracking system that could handle 50 employees, but cannot handle the influx of the 600 applications a week we’re now getting. There’s a transition period where we’re moving over from smaller company systems to bigger company programs, now that we can scale and we know that there’s no stopping us.”
• “Also, the importance of telling people that it’s also ok not to engage, which some people miss. How do we set the permissions for people not be involved with everything? Do people feel ok with that? We also have people who work remotely because they don’t want to talk all day and that’s ok, too. We have shared values and goals, and as long as we respect each other and get there, that’s what matters.”

TaxJar team members at JarFest 2019 in Nashville, TN

A healthy work-life balance is perhaps the ultimate personal benefit of being part of a remote staff to the individual. We’re all different, each fine-tuned by adulthood into unique beings with a specific set of pleasure and stress settings. For some workers – including Darcy Boles, in fact – the most productive workdays are the ones that begin with a few hours of surfing in the morning. A more rigid system of in-office work clashes with that unnecessarily, and pretty soon that worker is going to see his job as the enemy of his peace of mind – and that benefits nobody.

And then there are the environmental benefits, Boles reminds us. “I don’t need to-go lunches anymore. I go to the Farmer’s Market every week. I don’t forget my bag and have to drive back home because I’m not rushing to work and need a coffee because traffic sucked that day. As I said, with remote work, everybody wins. Communities win. The environment wins.”

TaxJar team members at JarFest 2020 in Savannah, GA

Boles adds a rather striking fact to illustrate the environmental benefits of a remote work model: “If half the U.S. worked just two to three days a week from home, and did so half of the time, it would be the equivalent of taking all vehicles in New York state and New Jersey off of the road in greenhouse emissions.”

All that said, a paradigm shift like moving from the old office model to the new remote model of working can be startling, and it requires that those interested in a remote position take a realistic look at the challenges of being a remote employee.

“I couldn’t be happier. TaxJar stands as a giant among progressive modern companies when it comes to employee happiness. I’m proud to be part of a growing company that puts its customers and its employees before everything else.”

“Familiarize yourself with the tools of remote work beforehand,” Boles says. “You can download Basecamp for free. You can download Zoom for free. If a remote company doesn’t use that exact tool, they probably use something similar. You also have to be able to over-communicate, which is really important. I should be able to pick up on any project that someone on my team has left off and know where they are. You have to really put yourself in the shoes of being a remote worker before you’re a remote worker.”

It’s clear that Boles and her fellow leaders at TaxJar are as proud of their remote workforce as they are of their product. And they should be, as companies like TaxJar are bold leaders in reimagining a working society, and making sure the human factor is always represented.

“We’re moving into this interesting age where things don’t have to be this industrial revolution hierarchical structure, there’s a lot more wire-framing,” Boles offers. “We’re moving into a kinder society, I think. And I think that shows with remote work. I want my team to surf every day or whatever makes them happy, but because the whole world doesn’t work remotely, we have an interesting challenge mentally that we have to break through, because we’re paving this way. And look at the results we’re getting. We’re obviously doing something right.”

“I look forward to working with fellow TaxJar employees each and every day. We truly have some of the most talented, creative, and impressive humans working here. The culture at TaxJar is very inclusive and set up to promote cross-collaboration all throughout.”

TaxJar’s CEO, Mark Faggiano, presenting at JarFest 2019 in Nashville, TN

TaxJar is breaking the mold and changing everything you think you know about work. Nine different stories. Nine different films. Nine different places. 20,000 customers, and one extraordinary team doing it their way. Check out the new #RemoteLife trailer here:

Learn more about the incredible individuals who though miles apart, together, help build the story of TaxJar every day. https://www.taxjar.com/jobs/#remotelife