Career Launch

Why TaxJar Could be a Great Place to Start Your Career

Jeremy Chevallier
February 2020

This article is part of a feature series on the best startups to launch your career this year.

Some companies know just how to make work feel personable.

TaxJar is one of those forward-thinking companies. Founder and CEO Mark Faggiano, in his 2017 post Welcome to TaxJar, Now Grab a Microphone, explains what culture means to him and to the company:

When you create a company, you’re not only trying to solve a problem for customers, you’re also creating a culture. […] Culture and a sense of togetherness is the difference between punching in every day, nine-to-five, and going through the motions, and feeling like you’re part of something special, something with a purpose.

Any company can say nice things like this, but the TaxJar team puts their money where their mouth is. They do that in the form of traditions, benefits, and a unique approach to employee-company relationships.

They have hilarious traditions you can partake in

If you want to work at TaxJar, you’d better be ready to sing. Forget sounding like a rockstar or giving your best performance ever—you just pick a song you love (that hasn’t been sung before) and perform it live to the entire remote team on a Zoom video call.

Don’t worry, though: you’re not forced to sing, which is what makes it great. TaxJar allows new hires to get comfortable in their new role without pushing them to do something they’re not ready for. Then, over time, employees choose to participate and feel even more a part of the team.

Mark Faggiano explains where he got this idea, and why it felt so powerful to him:

I borrowed the idea from my college days as a walk-on on the Boston College baseball team. On the first road trip of the season, every freshman sang a song in front of the team.

A couple of things really stood out from those days: first, the talk about singing started early in the school year, like in the first couple of practices. There was literally five months of buildup. That was more than enough time for a young mind to conjure up all kinds of anxiety. The other thing I took away from my experience was that singing the song made each player “officially” part of the team. From there on, the rest of the team had your back. That mean[s] everything to a 18-year-old freshman who looked up to guys two, three, four years older.

So, Mark decided to make it a part of TaxJar’s culture—and it has worked extremely well for bringing the team together. They even built into it a friendly competition, with the top three performers on the medal stand having done things like performed in a tuxedo, doing a juggling finale, and being accompanied by a pug in a reindeer costume.

If nothing else, a company that encourages its employees to sing is a culture that clearly appreciates what it means to live life to the fullest. And yet, this is just the beginning of reasons why TaxJar could be a great place to start your career.

They have awesome benefits and policies that you truly deserve

Yeah, every startup has generally good benefits, and many—like 401ks and full health, dental, and vision coverage—are practically must-haves nowadays. But TaxJar nails a few particular benefits that stand out in my opinion:

1. Free Amazon Prime and Spotify Premium

Spotify Premium and Amazon Prime both cleared 100 million subscribers in 2019 [1] [2], so you know this kind of perk is something new employees are likely to take advantage of. Who doesn’t love music and movies?

2. Gym and internet reimbursement

Because TaxJar employees work remotely, the company’s leadership wants to make sure they have a strong internet connection—and they’ll pay for it. Because computer work is pretty static, they want you to go to the gym—and they’ll pay for that, too. In fact, they’ll even give you $250 to invest in an ergonomic setup for your home office.

3. Mandatory vacation and birthday holidays

Like many startups, TaxJar’s policy used to be “unlimited” vacation—but they discovered that employees weren’t taking advantage of it, for a few reasons. CRO Ryan Thompson explains in Why We Switched from Unlimited Vacation to Mandatory Vacation:

Our company is full of go-getters. […] When you put so many competitive, high-achieving people in the same company, competition runs rampant. This is mostly for good, [but] there are also hints of internal competition where employees want to deliver just as much as the people around them at all times.

In this environment, an “unlimited” vacation policy became more of an “optional” vacation policy. […] Many teammates felt like they’d fall behind if they took time off, and let down their colleagues.

Leadership realized they needed to change the way the team thought about vacation time. So, they made vacation mandatory—a minimum of two full weeks—and even sweetened the deal with a $250 vacation stipend to those who take the time off. This is an investment in their team members’ health and productivity, and I bet it’s working wonders.

4. Parental leave for both moms and dads

Usually, when we think of parental leave, we think of moms nurturing their newborns. But dads staying home is just as important to babies, and TaxJar makes sure both Mom and Pop get to bond with their new bundle of joy.

5. $1,000/year for your personal development

This is my favorite of them all—simply because it’s so personal to each team member, and it’s not a small sum of money. TaxJar is so smart to offer this kind of perk because each employee can focus on their interests. If I were working at TaxJar, I’d spend this on self-defense classes and Vietnamese tutoring sessions!

They do mutual, paid trials before hiring

Gary Vaynerchuck has famously said that hiring is guessing. Similarly, CEO Mark Faggiano explained this in How One Change to Our Hiring Process Made All the Difference,

Early in our company’s history we discovered that our interviewing process didn’t yield obvious, no-brainer hires. Our hiring process was broken. […] Unfortunately, great intentions don’t guarantee great hires [and] neither does the traditional interviewing process. […] We had to do something different to make the correct hires, or else we were going to fail as a company. […] This was when the mutual trial period was born [to TaxJar].

TaxJar won’t hire anyone without first doing a mutual trial, because it’s such a valuable and insightful way to test the waters—both for the new employee and for the existing team. It answers core leadership questions, like whether the new hire can move the needle and thrive comfortably in the TaxJar ecosystem. And it helps employees decide if they can get excited about the problem TaxJar solves, the people they’ll be working with, and the distributed nature of the work.

Leadership treats trial members like employees, giving them the same level of trust and access, and fully immerses them into the existing team. Over the course of 80 to 160 hours working together, they build plenty of face time and project contribution. They set clear expectations upfront and go with their gut to communicate quickly once they know whether or not it’s going to be a fit.

This is truly a brilliant and unique approach to hiring that optimizes for win-win outcomes between candidates like you and companies like TaxJar. Big props to them on this one.

They’re hiring, and they’re open to proposals

Lastly, and although not a necessary checkbox to make this list of 20 Startups to Work at in 2020TaxJar is hiring right now. At the time of this writing, the only entry-level position is a Sales Development Representative (SDR), but don’t let that stop you if you’re trying to get into another career path like marketing or design. They also encourage you to email them if you don’t see a job that fits your experience!

I bet if you made a Crash pitch showing your excitement about their company (and showcasing a relevant project you’ve done), you’d get an interview. And, if you want that SDR role, here’s what you could do to practically guarantee yourself a trial:

  1. Research TaxJar’s ideal customer (hint: probably eCommerce stores).
  2. Make a spreadsheet listing a few businesses that fit the bill, the right person to contact in each one, and that person’s contact information (email, LinkedIn, Twitter, anything).
  3. Write an authentic outreach message that you believe would earn those business owners’ attention and get them interested in learning more about TaxJar.
  4. Create a Crash pitch with numbers two and three in the Portfolio section, and send it to the hiring manager for this role.

Hit me at jeremy [at] crash [dot] co (or anyone else on the Crash team—we’re always here to help!) if you want to bounce ideas on winning an interview with TaxJar.

Rock on. 🤘


Looking for opportunities at other cool startups? Check out this collection of the best startups to launch your career this year.

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