I'm Justworks Founder Isaac Oates, And This Is How I Work

Photo: Courtesy of Justworks

If you’ve ever struggled with an outdated payroll system, or slogged through a bureaucratic HR department, you can see the appeal of Justworks, which offers modernised payroll, benefits, HR and legal compliance services to small businesses and growing companies. It’s still a growing company itself, competing with legacy giants such as ADP as well as startups such as Zenefits, WageWorks and Gusto.

We talked to founder Isaac Oates about that classic startup origin story: Turning your own business’ pain points into your next business’ product.


Location: New York, NY

Current Gig: Founder & CEO at Justworks

Current mobile device: iPhone

Current computer: MacBook Pro

One word that best describes how you work: Efficiently

First of all, tell us a little about your background and how you got to where you are today.

I started as an engineer at Amazon, where I worked on “third party payments” (3PP), a transaction processing system that moved money between buyers and sellers on their marketplace.

After working on 3PP and going to business school, I transitioned into a product manager role at Amazon, but I eventually left to co-found an ad-tech company called Adtuitive. Etsy acquired us, and I went on to spent three years building out their payments platform, Direct Checkout.

I missed life as an entrepreneur, but it was during this time at Etsy that I realised how difficult the admin side of running a business could be. I just knew that there had to be a better, simpler way, which was ultimately my inspiration for Justworks. I wanted to build something that would make it easier for businesses to grow.

Take us through a recent workday:

  • Up early for an investor presentation in the morning.
  • Into the office for our weekly all-hands meeting. The focus is always different, but the overarching goal is to provide an opportunity for all 300+ of us to sync up across the company.

    As you might imagine, the format varies greatly. Depending on the topic, I might be presenting with other members of the leadership team one week and moderating a panel of employees for a fireside chat the next. We’re hiring and nearly always introducing new additions to the team.

  • After all-hands, eight shorter meetings throughout the afternoon including one-on-ones with my staff and status reports for key projects.
  • Left at 5PM to pick up my son from school.

What apps, gadgets or tools can’t you live without?

Like most entrepreneurs, I can’t live without the basics: Microsoft Word (writing memos), Excel (analysing data), Google Slides (making presentations), or my iPhone (I like to handle urgent issues via text).

What’s your workspace setup like?

Justworks is growing, so we actually just moved offices this year. We’re now in the Starrett-Lehigh building in NYC. We have a big open floor plan where all of us sit together, but people have their own workstations that are grouped into pods of six.

I usually spend my time at my desk on the floor with everyone else, but I also have a private office, mainly for meetings and calls. Open plan office spaces don’t work for every company, but it works well for us and the kind of team we are.

The Justworks office (Photo: Justworks)

What’s your best shortcut or life hack?

I take time over the weekend to start responding to my emails, but instead of sending them, I save them in a draft folder to blast out on Monday morning. That extra downtime on a Sunday spent in my inbox helps me reduce my own stress without dumping it onto my team over the weekend.

During the week, instead of responding to an email the moment it comes in, I use Apple Mail to read emails in big batches every couple of days. As I mentioned, I’m big on texting for urgent issues.

Take us through an interesting, unusual or finicky process you have in place at work.

We have a highly structured weekly leadership team meeting where leaders propose big decisions through written memos. We have a pretty firm protocol for these meetings — no memo, no decision. This standard has improved the quality of our thinking tenfold.

Who are the people who help you get things done, and how do you rely on them?

I am extremely lucky to have such a strong team surrounding me. Each of my VPs has a superpower, and I rely on them heavily to run the company.

Sabrina, my assistant, is instrumental in helping me manage my schedule with things that don’t fall in any VP’s scope, but still need to happen (that is, big events, presentations and scheduling).

Isaac’s desk (Photo: Justworks)

How do you keep track of what you have to do? 

I keep it simple. I usually have a running list in Microsoft Word of all the things I need to handle. Outside of that list, I email myself reminders of things that come up when I’m meeting with people.

How do you recharge or take a break?

I usually spend a few hours each weekend working on slower burn projects (memos, presentations and so on) and getting through email.

Aside from that, I really try to use my weekends to recharge. I also try to get away a few times a year and shut off my email entirely. I did this recently and took my son to Scotland for a week, which was awesome.

What’s your favourite side project?

As a former engineer, I really still enjoy data analysis and try to identify trends that no one else is seeing or may be harder to predict. It’s a nice way to validate hypotheses and makes me feel like I have a better handle on the business.

Isaac’s home screen (Screenshot: Isaac Oates)

What are you currently reading, or what do you recommend?

I recommend Peopleware: Productive Projects and Teams, by Tom DeMarco. It’s a great book about leading teams of engineers.

Who else would you like to see answer these questions?

President Obama.

What’s the best advice you’ve ever received?

Swim in your lane. Let your competitors take care of themselves.

What’s a problem you’re still trying to solve?

Justworks has been growing fast. This is extremely exciting, but with fast external growth comes a new set of internal challenges. While the whole team is focused on shared goals, long gone are the days of working within earshot of each other — literally and figuratively.

So I’m continually working on establishing and refining the right communications channels for the way we want to work: Efficiently. Making sure everyone on the team has access to the information they need is the foundation of our ability to keep growing the way we are.

We've asked heroes, experts and flat-out productive people to share their shortcuts, workspaces and routines. Want to suggest someone we should feature or questions we should ask? Let us know.


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