I’m the Founder of Justworks Isaac Oates and This Is How I Work

If you’ve ever had to deal with the legacy payroll system or work in the bureaucratic personnel department, you can be sure of attractiveness Justworks , which offers upgraded services for the calculation of wages, benefits, HR and legal services for small businesses and growing companies. It is still a growing company that competes with legacy giants like ADP as well as startups like Zenefits, WageWorks and Gusto. We spoke with founder Isaac Oates about this classic startup origin story: turning the pain points of your own business into the product of your next business.

Location: New York, NY. Current place of work: Founder and CEO of Justworks. Current mobile device: iPhone. Computer: MacBook Pro. One word that best describes how you work: effective.

First of all, tell us a little about your past and how you got where you are now.

I started out as an engineer at Amazon where I worked on “Third Party Payments” (3PP), a transaction processing system that moved money between buyers and sellers in their markets. After working on 3PP and going to business school, I moved up to a product manager position at Amazon, but eventually left to co-found ad technology company Adtuitive. Etsy acquired us and I spent three years building their Direct Checkout payment platform.

I missed the life of an entrepreneur, but it was during this time at Etsy that I realized how complex the administrative side of running a business can be. I just knew there had to be a better and easier way, which ultimately became my inspiration for Justworks. I wanted to create something that would make it easier for the business to grow.

Tell us about your recent work day:

  • Get up early for your investor presentation.
  • To the office for the weekly general meeting. The focus is always different, but the common goal is to enable all 300+ of us to sync within the company. As you can imagine, the formats are very different. Depending on the topic, I could give presentations with other members of the steering group for one week and moderate a group of employees for a chat by the fireplace. We are hiring and almost always introducing new additions to the team.
  • After general meetings, 8 short meetings throughout the day, including face-to-face meetings with my staff and status reports on key projects.
  • Left at 5 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 notes), Excel (analyzing data), Google Slides (making presentations), or my iPhone (I like solving urgent issues with text).

How is your workplace arranged?

Justworks is growing, so we only moved to the office this year. We are now at the Starrett-Lehigh Building in New York. We have a large open floor plan where we all sit together, but people have their own workplaces, grouped into groups of six. I usually spend time at my desk on the floor with everyone, but I also have a personal account, mainly for meetings and calls. Open-plan offices are not suitable for every company, but they are suitable for us and our team.

What’s your best shortcut or life hack?

On weekends, I take the time to start replying to my emails, but instead of sending them, I save them in my draft folder to send on Monday morning. The extra Sunday downtime in my inbox helps me reduce my own stress without putting it on my team over the weekend. For a week, instead of responding to an email when it arrives, I use Apple Mail to read emails in large batches every couple of days. As I mentioned, I am good at texting for urgent matters.

Tell us about an interesting, unusual, or challenging process you have at work.

We have clearly structured weekly executive meetings where executives propose important decisions in written memos. We have a pretty solid protocol for these meetings – no memos, no decisions. This standard has improved the quality of our thinking tenfold.

Who are the people who help you achieve results, and how do you rely on them?

I am very lucky to have such a strong team around me. Each of my vice presidents is superpowered and I rely heavily on them to run the company. Sabrina, my assistant, helps me manage my schedule with things that are outside the VP’s purview but still need to happen (like big events, presentations, and scheduling).

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

I’m simple. I usually have a current list in Microsoft Word of everything I need to do. In addition to this list, I email myself reminders of things that come up when I meet people.

How to recharge or relax?

I usually spend a few hours every weekend working on slower recording projects (sticky notes, presentations, etc.) and forwarding emails. Also, I try very hard to use the weekend to recharge. I also try to leave a few times a year and turn off my email completely. I did it recently and took my son to Scotland for a week and it was great.

What’s your favorite side project?

As a former engineer, I still love data analysis and try to spot trends that no one sees or that might be more difficult to predict. It’s a good way to test hypotheses and make me feel like I’m better at business.

What are you reading now or what do you recommend?

I recommend Peopleware: Productive Projects and Teams by Tom DeMarco. This is a great book about leading engineering teams.

Who else would you like to see to 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 problem are you still trying to solve?

Justworks is growing rapidly. This is very exciting, but with rapid external growth, a new set of internal problems arises. While the entire team is focused on common goals, long gone are the days when we worked within earshot of each other – literally and figuratively. So I am constantly working to establish and refine the correct communication channels for how we want to work: efficiently. Ensuring that everyone on the team has access to the information they need is fundamental to our ability to continue to grow as we are.


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