Female legal tech founders told Insider about the sexism and questions about their dating life they faced while breaking into the male-dominated industry

  • Female founders receive less funding and encounter more resistance in the tech world.
  • Women make up 20% of Big Law equity partners, but only 14.5% of legal tech founders are women.  
  • 7 lawyer-turned-founders spoke to Insider about the bias they faced while pitching to investors.
  • See more stories on Insider’s business page.

Basha Rubin was in labor when she negotiated the term sheet for her Series A.

In May last year, Rubin hashed out investment details for Priori Legal, an attorney hiring platform for companies, clutching her phone as her partner drove them to the hospital.

“They were on these curvy roads and she had the phone like this,” said her co-founder Mirra Levitt, holding her palms out in front of her face. “It was like watching a video game.”

Experiences like Rubin’s are not uncommon among working women, who often face hurdles that their male colleagues don’t. This is especially the case in law and tech — two industries that have historically struggled with diversity. Women make up only 31% of nonequity partners and 20% of equity partners in the 200 largest law firms, per data from the American Bar Association. In the tech world, just 28% of startups have a female founder, according to a 2019 Silicon Valley Bank report.

The numbers are bleaker when you look at the intersection of the two industries: There are only 14.5% female founders of legal tech companies, according to a study by Kristen Sonday, cofounder of the legal tech platform Paladin.

Female legal tech founders receive less funding 

Although venture capital investments in startups increased by 13% last year, women-founded companies received only 2.2% of funding in 2020, according to data from Pitchbook.

“The tech world seems so male-dominated not necessarily because there are so many more male founders. It’s because the male founders are so much more well-funded than the female founders,” said Rubin.

Priori Legal, which raised $6.3 million in its Series A, was “tremendously lucky” to have the backing of the female-founded accelerator HearstLab, according to Levitt.

Many female lawyers who left law firms to launch their own legal tech companies said they were surprised to meet resistance in the supposedly more forward-thinking tech world. 

“It’s odd because the legal industry still felt like more of a safe space for me, where I felt like people were more open to treating me as a professional as a woman,” said Alma Asay, founder of Allegory Law. “When I was raising money, I remember one investor saying, ‘You’re new to Palo Alto. You’ll meet a lot of great guys out here.’ And I thought, why are we talking about this? I’m trying to pitch you.”

Three founders told Insider that investors asked them about their family plans during pitch meetings.

Hearing comments like these made Asay feel deflated. “I could take all the advice in the world and change my pitch deck, the way that I presented, but the one thing I couldn’t change is that I’m a woman,” she said.

Erin Levine said she held off on raising money when she first launched Hello Divorce because she expected to face this kind of bias from investors. Instead, she did a lot more bootstrapping, “partly because we had to, since women don’t get funded as much as men do.”

Laura Safdie, a lawyer who founded Casetext, said she didn’t encounter sexism while pitching to investors. But she says that’s “very possibly” because her cofounder and CEO is male.

‘Clients feel more comfortable hiring companies that are male-run’

Legal tech female founders face similar challenges when pitching their products to clients, a task that’s already made difficult by the relatively tech-resistant legal industry.

“As a female-run business, it’s very apparent that clients feel more comfortable hiring companies that are male-run,” said Nicole Bradick, the founder of Theory and Principle. She recalled an instance when a chief information officer of a firm said he won’t meet with women unless other people aren’t in the room, because he didn’t trust them otherwise.

Bradick said she once lost business because she rejected a romantic advance, but added that these “horrendous” incidents are not common.

On the other hand, acting as a salesperson in legal tech can be an “equalizer,” said Julia Shapiro, founder of Hire an Esquire.

“You’re the main salesperson as the founder. Law firms are used to both men and women selling products to them,” Shapiro said. “They can be equally mean to both — they’re skeptical of vendors in general, and will cross-examine them.”

Pushing for diversity in legal tech

Despite the barriers they’ve faced in the tech world, the women who spoke to Insider said they are taking steps to instill diversity within the companies they run — and the industry writ large.

Asay said she placed particular emphasis on hiring women at Allegory Law, though it didn’t come easy given the dearth of female engineers and some of her own internal biases.

“I almost didn’t extend a woman an offer because the way she was coming across wasn’t as assertive, self-promoting, and confident as a man would,” she said. “I had to check myself, because this right here is the problem. Women have some imposter syndrome and don’t themselves up as much, but it doesn’t mean that they don’t have the same — or more — talent.”

In addition to ensuring accountability among partners at law firms and from clients, the growing community of female founders in legal tech are taking steps to support diversity within their companies.

“As a female founder, one thing that’s really empowering is to build a company and set a culture that aligns with my values,” said Casetext’s Safdie. “It’s not easy. It’s something you have to keep doing over and over and not let backslide.”

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