About Sixty

We are a Y Combinator-backed startup based in San Francisco.

Our journey began years ago as web agency owners focused on building Squarespace websites. In 2016 we founded Sixty.

To date, Sixty has helped thousands of clients hire freelancers and agencies – from Silicon Valley startups and small businesses to enterprises like Creative Artist Agency and institutions like Stanford, Brown, and Yale.

Recently, we expanded our service for Squarespace clients. Now we're introducing clients with any sized project to a curated group of professionals they can hire. After Squarespace, we'll scale this service to the rest of the digital service economy.


We're increasing efficiency and stability within the digital service economy.

  • For freelancers and agencies: producing a steady stream of leads that they want.
  • For clients: introducing them to the best available freelancers and agencies for their project.


There are problems for both the freelancers and agencies working within the digital service economy and the clients hiring them.

For freelancers and agencies

The digital landscape is architected in such a way that:

  • Simultaneously marketing yourself and delivering on client work is difficult – resulting in terrifying “feast and famine cycles”.
  • Being loud online produces more leads than doing great work.

For prospective clients

It takes dozens of hours to find someone who:

  • Is available – a large percentage of the freelancers and small agencies you'll see online don't take clients anymore.
  • Has a track record of success delivering on projects like yours, for clients like you.
  • Wants to work with you, so much so that they'll work harder and lower their price.

Who We Are

David Head

Co-Founder, CEO

David keeps his head in the clouds. He's our “big ideas” guy and makes the epic plans for how we're empowering creative professionals to work with greater efficiency and freedom. Sometimes David's predictions about the future sound crazy, but more often than not he's right. We've learned to trust his gut. Before Sixty, he started multiple other businesses, most recently a web agency that built over 100 Squarespace websites. He believes in the power of meditation and trains Brazilian Jiu Jitsu.

David received a degree in Entrepreneurship from Belmont University. While there, he won a few business awards and competitions. Most notably, being recognized as one of the top 5 student entrepreneurs in the US by the GSEA.

David's first business was formed around the cheap wayfarer sunglass fad. People would build their own pairs of glasses to match their favorite sports team, their club's colors, or their pajamas (like one person who bought 5 pairs).

Alex Tapper

Co-Founder, COO

Alex keeps his hands in the dirt. He rallies the community around a common goal: working 1-on-1 with clients to produce the best work together. That means a lot of facetime advocating our mission. He knows that good design changes the way we experience the world and that words matter—a lot. In another life, Alex wrote songs and branded business across Nashville. He believes in the power of routine and does at least 1 handstand every day.

Alex graduated from Vanderbilt University after studying Classical Guitar, English Literature, and a little bit of Computer Science. He was in some B.S. Honors societies, but is more proud to have led the Rugby team to an SEC Championship in a defensive 9-3 victory over Auburn.

Alex's first business was selling pizza “by the slice” to hungry dorm-mates at boarding school after check-in. It was kind of a monopoly—his customers were literally locked into the building without another option. His secret? The smell of hot pizza drew the crowds, but he made the real margins on cans of soda.

Andrew King

Co-Founder, CTO

Andrew keeps his eyes on the prize. He connects the dots between our present position and our lofty ideas. That means he's often knee-deep “in the code” squashing bugs and building new features. Grounded and with extreme attention to detail, Andrew reminds our team of the stiff reality of logic and reason—but thanks to him we're always up to best practice. Before Sixty, Andrew built interfaces for top-secret consulting projects. A competitive sailor, he believes in the power of tactics and complains regularly about not being out on the water.

Andrew graduated from Vanderbilt University with a degree in Economics and Corporate Strategy. He served in leadership roles in numerous collegiate organizations, so he knows a thing or two about organizing the unorganizable.

Andrew's first business, Mellodi, is a platform that connects college musicians with local on-campus fanbases. The platform remains active, but Andrew put it on the backburner after realizing that he'd successfully hit the ultimate cross-section of non-paying users: college students and musicians.