How Working Remotely Helps TaxJar Employee Heather Wilson Be Happier And More Productive

This article is part of the Rise of Remote Work LinkedIn Newsletter covering stories and insights from remote work leaders, experts, and advocates around the world. Hit subscribe to get notified and share your thoughts in the comments.

As part of my LinkedIn Newsletter series about the Rise of Remote Work, I had the pleasure of interviewing Heather Wilson, Employer Brand Architect at TaxJar.

A native of Miami Florida, Heather Wilson, CMP is Storyteller, Employer Brand, and Events Architect on the People Experience Team at TaxJar. She is passionate about sharing how remote work allows freedom from limitations, and the ability to build a career and life where and how one wants. Now based in the Ozark Mountains of Northwest Arkansas, she has a small farm and apiary where she loves spending time with her husband, and two rescue dogs; a French Bulldog named Taco and a Great Pyrenees named Bella. She talks to her bees every day. 

Thank you so much for your time, Heather! Can you tell us a bit about your ‘backstory’ and how you got into remote work?

For my entire career, I’ve been remote in some way, though perhaps not in the ‘traditional’ sense of the word. I used to spend 175+ days a year on the road and in the sky since my work always required extensive global travel. It’s always felt natural for me not to be in an office five days a week.

The catalyst to a “true remote” move happened while I was living in San Diego. I met my husband while he was stationed there with the military. He’s a dad, and it was one thing to live away from his children because the military says you have to. When he finished his military career, the choice of where to live became ours. We decided to make a major move to be near my stepdaughters – to his native rural Northwest Arkansas. I asked my employer at the time if I could work remotely, and they agreed without hesitation. I’ve been remote ever since.

What, in your opinion, are the key benefits of working remotely compared to a traditional 9-to-5 office job?

I think it’s important to consider my carbon footprint. I use much less of our planet’s resources working remotely than I did going to an office.

Those times I did commute in Southern California, two hours (and sometimes more) of my day was spent going a mere 24 miles (39km), round-trip. I think it’s important to consider my carbon footprint. I use much less of our planet’s resources working remotely than I did going to an office. Fighting traffic, dodging accidents, and wondering if you’ll be “on time” isn’t the way to get your day started – or to be your most productive self. Time is a precious thing, and we don’t get it back. Entering an office building doesn’t suddenly mean you’re “on,” or tuned in.

We’re also not limited by geography in our candidate searches, which means I get to work with THE brightest and smartest teammates I could ever ask for. Seriously, I’m constantly blown away with what our teams are doing, and to know that as TaxJar grows, that feeling will continue is really exciting.

We’re also not limited by geography in our candidate searches, which means I get to work with THE brightest and smartest teammates I could ever ask for.

I also love that social interaction within a remote environment is more meaningful and intentional. You are not under the constraints of social conventions to have ‘water cooler’ chat, and disruptions are further and fewer between. Cake Wars, Halloween costume contests, open mic nights, and JarFests each have their own countdown. You can feel the excitement through Basecamp (project management + internal communications tool), and that’s pretty powerful.

Plus, in relationship to TaxJar – I have to mention trust. It’s incredibly validating to work as part of a company that trusts me to do my job, to do it well, and in the place that I define and create as best for me. 

Of course, controlling the thermostat and having my dogs nearby is great, too!

That sounds awesome. So how long have you been working remotely and what lessons or ‘key takeaways’ have you learned along the way?

It’s been five years now that I don’t have a “physical corporate office.” There are so many lessons along the way that books have been written about it. My top two:

1. I’ve learned patience. Answers don’t always come right away across time zones, and there are no ‘drop-ins’, so planning out tasks is important. 
2. Permission to stop. When you love your work, it’s easy to keep going and going. There’s a lot of inspiration in loving what you do. But when you work remotely, there is sometimes no differentiation between your workspace and your personal space. It’s important to remember that there is life outside of work and to take time to recharge-whether that’s a vacation or just stepping away for a workout, to eat lunch, or walk your dog (real talk: I’m still working on this one.)

Tell us a bit more about TaxJar. How is remote work encouraged within your team or organization?

TaxJar is an all-remote SaaS company in the FinTech space. We automate sales tax calculations, reporting, and filings for eCommerce businesses. On the surface that may not sound very exciting, but when you think about the time we give back to entrepreneurs and businesses, it’s extremely gratifying. They can use that time to spend on building their businesses, family, or whatever they want. 

We’ve been remote since day one. It’s part of our DNA; and it’s one of our core values. Our CEO, Mark Faggiano, has been very open about sharing that he doesn’t care when or where we work. He just cares that we do our best work. He and the rest of our leadership team lead by example. Our work “environment” is extremely intentional and thoughtful. Everything from an office allowance to our on-boarding process ensures we’re set up for success from day one. The investment that would have gone into a physical building is instead put back into the team. 

We’ve been remote since day one. It’s part of our DNA; and it’s one of our core values. Our CEO, Mark Faggiano, has been very open about sharing that he doesn’t care when or where we work. He just cares that we do our best work. He and the rest of our leadership team lead by example.

Can you share a few of the biggest challenges you or your team have experienced while working remotely? And what have you done to address those challenges?

Scaling a business through rapid growth can present challenges for any company, and remote definitely presents its own set of growing pains. A smaller team that was involved in all decisions -like hiring- suddenly finds those responsibilities going to new teammates. They’re not able to stop by someone’s office to meet them or go to a newbie lunch, so they’re left having to trust the decisions that went into growing the business. 

Going from knowing all the faces on Zoom and avatars in Basecamp to scrolling through pages of faces, some of whom you don’t necessarily recognize right away can be disconcerting. At TaxJar we’ve been purposeful about making sure we’re building our culture together. From holding Friday FaceTimes to introduce and get to know new team-members to very deep culture work, we’re making sure that the entire team is involved in our growth.

I’d also add that as a 100% remote company, you have to be prepared, willing, and able to have tough conversations via video calls. If you aren’t prepared for the transition from office to remote, it could be a bit tough at first. You aren’t able to hash things out in-person, do a quick drop into someone’s office then go grab a cocktail after office-hours. Text and tone can be lost in Basecamp chats, and it’s important to give the benefit of the doubt and keep yourself in check when the inclination to do otherwise may strike.

Of course, the aforementioned shutting down at the end of the day can be hard, especially when working across time zones. You just have to remind yourself no one is expecting you to reply after hours, and it’s ok to be asynchronous when you need to be; the big stuff can be scheduled for discussions at a time that works for everyone. Rest and recharging are important – no one wants you trying to pour from an empty cup.

As a 100% remote company, you have to be prepared, willing and able to have tough conversations via video calls. If you aren’t prepared for the transition from office to remote, it could be a bit tough at first.

Any advice around making sure employees are both happier AND more productive while working remotely?

At TaxJar we have a major emphasis on a collaborative culture through transparency and communication. There are no egos – we’re very open about that. We have regular check-ins with each other and Mark, our CEO, shares a daily update of the financial status of the business, as well as a weekly and monthly update. There’s peace of mind in transparency. 

We also meet once-a-week as a company to share what’s going on with the business, give each other kudos, and check out other teams’ demos (I look forward to this each week). Sometimes we sing or have a surprise dance break or theme the call – Crazy Hair Day was really fun! 

At the same time, we’re not over-scheduling meetings, and as a team built on trust, there is no micromanagement. Of course, we have tools in place to allow for feedback. For example, the People Experience Team checks in with everyone through OfficeVibe. 

Ultimately, we know that even though we’re remote and it’s across many miles we’re building TaxJar’s story, together. When you trust your team to do their very best work, give them the tools with which to do it and make sure they know how their contributions move the needle, they’re motivated to be productive, and not just meet expectations, but exceed them. 

When you trust your team to do their very best work, give them the tools with which to do it and make sure they know how their contributions move the needle, they’re motivated to be productive, and not just meet expectations, but exceed them.

That's really great. So why, do you think, traditional companies still hesitate to adopt remote work?

They’re unsure how to get started, and they lack trust. Often leadership is worried about how to keep tabs to make sure employees are actually doing their work. I’ve been on calls where directors sit in just to make sure their reports are conducting calls. That’s awkward, unnecessary, and it sends the wrong message. If you don’t trust your employees, why should anyone else? 

Figuring out setup is fairly easy to resolve; there are great resources for getting started in transitioning to remote, but if you’re dealing with the latter, it’s time to examine your culture. 

Why would you hire a team you don’t trust to get their work done?

Could you share your thoughts around how the coronavirus pandemic might change the way we work?

COVID-19 is already changing the way we work. In a matter of months, the world transitioned from office commutes to forced work from home. It’s a shame that a global pandemic introduced this type of work to society, but now that some time has passed, many are seeing the benefits. Each day we’re hearing new announcements from some major companies that they’re deciding to stay remote. More will follow suit. 

It’s also forced closer examination of risk plans. Corporate security will become more important and companies will take a look at how they’re maintaining networks. Remote companies were already set up for this and didn’t skip a beat.

Finally, many in niche industries will begin cross-training to make themselves more marketable. For instance, hospitality and events have taken a huge hit. Event and meeting planners who have previously conducted live streams have had easier transitions pivoting to virtual events. Across all industries, many will be examining their career paths more closely in preparation for the ability to cross over into other spaces.

COVID-19 is already changing the way we work. […] now that some time has passed, many are seeing the benefits. Each day we’re hearing new announcements from some major companies that they’re deciding to stay remote — more will follow suit.

What's your #1 remote work tip for those making the leap into remote work post-COVID-19?

A colleague recently pointed out that while a few years ago not having an office may have been peculiar, the investment in personalized content and education will lead the charge. Remote is now seen as a core strength. Use this strength and leverage it to move your business forward. Take the first step. Make like a Nike – and “Just Do It.” And I’d be remiss if I didn’t add – always do right by your team and they’ll be driven to do right by your customers.

Remote is now seen as a core strength. Use this strength and leverage it to move your business forward. Take the first step. Make like a Nike – and “Just Do It.”

Thank you so much for sharing these valuable insights! How can we further follow your work?

As pioneers of true remote, TaxJar wants to help, and to inspire those businesses and individuals discovering and considering going fully remote. I’m honored and proud to share we recently won a Telly Award for our docuseries of nine short films called #RemoteLife. We hope they change the way people think about how “work works, ” and let the world know a great work/life integration can exist. You can check out the trailer here, and all nine films here.

We’d love to connect with everyone on social media. You can find us on Instagram, Facebook, Twitter, TaxJar’s LinkedIn, and you can also check out our Life Blog for the latest from TaxJar. For those who’d like to stay in touch personally, please feel free to reach out to me on my personal LinkedIn. 

I look forward to hearing from everyone, and thanks again for having me, Mandy!

This article is part of the Rise of Remote Work LinkedIn Newsletter covering stories and insights from remote work leaders, experts, and advocates around the world. Interested to learn more about remote work? Feel free to schedule a 30-minute strategy session or download your free remote work policy checklist.

About The Author: Mandy Fransz

Mandy Fransz is the founder & CEO of Make the Leap Digital, a boutique consulting firm helping businesses digitally transform the way they work. Mandy co-manages the fast-growing Remote Workers on LinkedIn group (+65K members) and she has been featured in (inter)national media including Thrive Global, LINDA, and AD Rotterdam.