Hear How This Yale Grad Took Squarespace Global

An accomplished Yale University graduate returned to New Haven Tuesday night to speak before an audience of 110 on the StartupGrind stage.

Moderated by StartupGrind New Haven Director Adam Muniz at Gateway Community College, attendees were given entrance into the analytical mind of Andrew Bartholomew, a 2009 Yale graduate.

A Philadelphia native, Bartholomew graduated from Yale with a degree in psychology. His path toward law school took an unexpected turn when he accepted a job offer at the New York County District Attorney’s Office as a policy analyst.

Bartholomew managed to teach himself the complicated methods of applying analytics and coding to create statistical-based reports for the city department.


But this endeavor wasn’t meant to last, as he became a business intelligence team lead in 2012 before entering his current role of vice president of strategy at Squarespace last August.

The company, established in 2004, now has 554 employees in New York City, Portland, Wash., and Dublin, Ireland.

The international company has served over one million paying customers helping create “millions of websites” and raising $78.5 million in venture capital funding.

Bartholomew quickly climbed the ladder of Squarespace, helping the software-based content management system establish and diversify sophisticated algorithms, building marketing analytics, forecasting future investments, and using multiple coding languages like Python and JavaScript.

When it comes to leading his group of 12, Bartholomew said the hardest thing to do is win the trust of the people on your team.

“I’m very transparent with people and I give very direct feedback, and I make sure they know I trust them and that I want them to grow and succeed,” he said.

Squarespace is a product-oriented company, he said, as they progressively and actively improve their quality-based software.

“We think it’s really important for people to tell their story in their own way,” he said. “Quality gives us more pricing power, and gives us the ability to invest really forward thinking stuff technologically.”

While Squarespace uses mainstream tools like Google Analytics and Zendesk, they are heavily reliant on proprietary software built by internal data engineering teams, he said.

Bartholomew said the company decided to build a recognizable brand and go where small competitors couldn’t by investing in advertising across comprehensive airwaves.

In February, Squarespace then spent around $5 million for a Key and Peele-featured Super Bowl commercial. The commercial received immensely positive reviews, garnering large traffic in the days to follow the nation’s largest televised event by using social media to elongate the ad’s shelf life.

Aside from the largest form of advertising imaginable, the company examines a market before advertising through pay-per-clicks, podcasts, and other television programming options.

The 12-month stretch of efficient marketing before joining the Super Bowl viewing experience “was a moment of extreme acceleration for us,” Bartholomew said. The company has since focused on internationalizing their audience—a sign of major growth.

Squarespace is always looking to expand, Bartholomew said, as they continue ranking markets to join through offering more access and enabling additional language options.

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