Building a Fast-growth SaaS HR Technology Company: Justworks CEO Isaac Oates (Part 2)

Sramana Mitra: How long did you have to stay at Etsy?

Isaac Oates: I was there for three years. It was pretty crazy actually. While I was there, I kept thinking about my time at Adtuitive. There were three founders and I was the one doing all of the paperwork, payroll, and insurance. I spent a lot of time with our fax machine.

I thought, “There’s got to be a way to use a computer to do all these things.” While I was at Etsy, I started to think about what I would do after Etsy. I kept coming back over and over again to this problem. Everybody that I talked to was petrified of employment and all the things that employment entailed. I thought there was this opportunity for a business. I thought there was a way to hire and pay people and not be completely stressed out about it.

Sramana Mitra: What particularly is so stressful? There are very large online payroll providers that can take care of payrolls. It’s not like that space has not been addressed. Where did you find the gap in that space that warranted starting another company?

Isaac Oates: It wasn’t payroll and insurance that was unsolvable. It was just deaths by a thousand cuts. If you’re an entrepreneur, there are two things. One is that you want to spend your time on things that push your business forward, which most certainly is not that kind of administrative work.

The second is that your time is unbelievably valuable. Your time just gets sucked away. When I looked around in the market, what I discovered was there were essentially two kinds of offerings. There were, what I would call, tightly bundled offerings where you could go to one provider and they would hook you up with everything. They would do the payroll. They would do all the filings and the registrations. They would get you the insurance and other kinds of benefits. That seemed great, but they were really expensive and their online products are terrible.

By terrible, I mean you can sign in on Internet Explorer but not on Mac. Then there were the other kinds of providers, the traditional ones where they’re a piece of the puzzle but it’s left to the entrepreneurs to stitch the pieces together. The other thing about is it’s anxiety-inducing because there are a lot of unknowns for the new entrepreneur.

The classic example being that you start your business in New York and you pay your first employee. You get this letter from the State stating that you haven’t set up your worker’s compensation insurance and that you owe thousands of dollars in fine. It just makes their stomachs turn. What I didn’t find was that something that would do everything for you, but was affordable and easy to use. That’s what Justworks is.

This segment is part 2 in the series : Building a Fast-growth SaaS HR Technology Company: Justworks CEO Isaac Oates
1 2 3 4 5