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Karen Colangelo didn’t plan to become a lawyer, although she grew up with two attorney parents in a small town near Buffalo.
“I always had an awareness of the legal profession, but I didn’t want to be a lawyer,” she says. “Like many people, I got into law because I wasn’t sure what else I wanted to do, but it certainly was not my intention.”
Once she started practicing, Colangelo realized pursuing law was the right decision, because she liked what she was doing. She found her niche in technology law, where applying old laws to new technology sparked her interest. Today, Colangelo serves as head of litigation and regulatory for the visual inspiration platform Pinterest, where she navigates complex content and moderation issues that impact both business and society.
The journey to this position started in 2010, after Colangelo graduated from Boston University School of Law. She joined Cooley’s Boston office as part of the law firm’s first class of summer associates. “At the time, there was a big case for Google that was being worked on by partners in San Francisco, and they needed someone to do all the grunt work in Massachusetts,” she recalls. “They asked me to do it, and that ended up turning into a whole career.”
As she became more familiar with tech law, Colangelo moved to California to work in the firm’s San Francisco office. There, she forged relationships at Facebook, Google, Twitter, and other Silicon Valley tech firms. In 2017, she joined Twitter’s litigation and regulatory team.
“I was there for five years, and I rose to the head of the litigation, regulatory, and competition team,” she offers. “I left in the Elon Musk debacle. I was the one responsible for suing Elon Musk to force him to buy the company, which was a bittersweet victory because of what he did.”
Unsure of what to do next, Colangelo briefly worked at Open Sea, an NFT marketplace startup. After eight months, her old boss from Twitter invited her to join Pinterest, and she’s been at the company since the summer of 2023.
At Pinterest, Colangelo manages all litigation and regulatory matters. Anytime Pinterest gets sued or there’s a threat of a lawsuit and anytime there is an enforcement action or investigation, Colangelo’s team handles it.
“With the tech industry, we’re in a new world where we have regulators supervising us, so we have to go in and meet with them on a bimonthly basis, answer their questions, and tell them what’s going on at the company,” Colangelo explains. “My team is responsible for that, so we’re trying to wrap our arms around it. We needed to develop a new strategy and build those relationships.”
One of Colangelo’s goals for her team is to take a data-driven approach to litigation. She provides leadership with metrics so they can easier assess the value of her team’s work.
“A lot of times, we may present a suit or reduce a settlement, and those are hard things to measure,” Colangelo shares. “I’ve been working on a project to better show the value of the team.”
“Karen is an exceptionally talented lawyer,” says Sarah K. Eddy, a partner at Wachtell, Lipton, Rosen & Katz. “Her strategic sense is spot-on, and she brings to every decision the right blend of focus and ingenuity. You couldn’t hope for a better partner and counselor in a tough situation.”
Throughout her career, Colangelo has observed the intersection of tech and law and has evolved her thinking and work to stay successful in the field. Still, there have been challenges.
“The No. 1 challenge is that we are a platform for user-generated content, and [such platforms] have a lot of capacity for good, but some people do post bad content,” she explains. “Unfortunately, a lot of people tend to seize on the negative parts of it. Especially since 2020, it’s been an industry in the crosshairs of political battles. It seems no one likes us.”
A critical issue for Pinterest and other platforms is Section 230 of the Communications Decency Act. This law says companies aren’t responsible for user-generated content that people post on their platform. But that law is under scrutiny, and President Donald Trump has said he wants to get rid of it.
“We try the best we can to monitor the content, but there are billions of pieces of content that people upload,” Colangelo says. “That’s a big challenge.”
Colangelo’s work at Twitter included defending the platform in Twitter v. Taamneh, a Supreme Court case that involved families of victims of terrorist attacks trying to hold platforms liable for the deaths of their family members. The argument was that Twitter content had radicalized these people.
“It was a hard case. You feel empathy for the plaintiffs and the victims of the suit, but at the same time, there’s no tie between these terrorist attacks and what happened on our platform,” Colangelo says. “We were protected by Section 230 because this was user-generated content, and we can’t be responsible for monitoring every single piece of it. It was a good win for platforms and a great experience for me.”
Colangelo leads a lean team of three (soon to be four), and loves being part of a “small, scrappy” squad. “It gives you a lot of opportunity,” she says. “At the bigger companies with hundreds of attorneys, everyone is siloed, working on one specific thing. We get to work on everything across the world.”
In 2024, Colangelo took on a new role advising Pinterest’s public policy team, helping analyze new laws as they come into play. This year, she expects lots of new challenges coming under the new presidential administration, which will make things fun and stimulating.
“We try the best we can to monitor the content, but there are billions of pieces of content that people upload. That’s a big challenge.”
Karen Colangelo
Away from work, Colangelo cherishes her time with her kids, ages three and six, who help keep her busy. She also enjoys going to comedy shows and seeing live music.
“This was the year of my nostalgia tour,” she says with a smile. “I went to Vegas to see the Killers for their 20th anniversary performance, and we also saw Incubus, Weezer and the Flaming Lips—all the old bands that were popular [when I was growing up].”
As someone who loves to learn new things, Colangelo gets what she needs to be inspired by her job by working in-house at a tech company. “Every day, I get to deal with new issues I never faced before, and it never gets stale,” she says. “As long as the pace of technology innovation happens, I want to stay on the forefront.”
