Headnote CEO Sarah Schaaf on Breaking Barriers in Legal Tech

As we celebrate Women’s History Month, we typically think of all the women who broke glass ceilings long before our time such as Marie Curie, Eleanor Roosevelt, Rosa Parks, and Amelia Earhart. But there are women who walk among us every day who continue to break barriers (and in current history, Kamala Harris, who was recently sworn in as the first female Vice President of the United States.)

Yet, it is no surprise women still face many obstacles when it comes to equity and acceptance in certain professions. Industries such as legal tech and venture capital, largely dominated by white males, are slowly moving the needle when it comes to increasing diversity, but they still have a long way to go.

Luckily, there are women who aren’t taking “no” for an answer. They are building women-led teams and bringing in male allies to push the boundaries. They are putting in the long hours, the sweat equity, and even the guilt over being a working parent, to make a difference and pave the way for the next generations.

Starting A Company

One of those women is Sarah Schaaf, the co-founder and CEO of Headnote. I recently had the opportunity to catch up with Sarah on 4 the Record to learn more about why she started her company, what it was like trying to raise funding in a male-dominated environment, and what young entrepreneurs can do to be successful.

As a former practicing attorney, Sarah founded Headnote (a legal industry compliant payments platform) because she knew there was an issue with the payments process. She explains:

“I grew up the child of two attorneys, both of whom started their own firms, and I knew how hard slow payment times were on small firms, so I wanted to make a really accessible, beautiful modern product in the lives of lawyers and law firms everywhere, regardless of size. And for me, and based on my experience, getting paid and making that easier and removing friction was the best way that we could improve the lives of lawyers everywhere.”

However, when it came to getting funded, Sarah found both luck and hurdles. Her first bit of luck came in the form of a female investor who led Headnote’s seed round and became Sarah’s closest advisor and friend, as well as others who were willing to help and pay it forward.

“I had a lot of amazing women that did help me get here, but also had some really amazing male allies that are major feminists and are trying really hard to shift the dynamic in the VC and the technology space to make it more equal between men and women,” she said.

Confronting Diversity Challenges in Venture Funding

But when Sarah set out for her first round of venture capital funding, she faced unique challenges and uncomfortable questions about family plans and pregnancy – questions her male counterparts would not be asked. That led to feelings of guilt, frustration, and questions about work ethic. Given that Sarah’s husband was her co-founder, there were added complications about what his role in both the business and the family would be. “For sure it put a lot of added pressure on our family. I think we knew that\’s what we signed up for. But I would love to work with male and female colleagues in the Valley to try to shift that dynamic and that feeling that you have as both a male or a female entrepreneur around having kids, because I know men who have the same feeling that are saying, ‘We give maternity and paternity leave 12 weeks’ or whatever it is, but they\’re not comfortable taking it themselves as a father because they don\’t know what it\’s going to say about their work ethic. And I think as a culture and a society in general, we need to work really hard to remove some of that stigma.”

Sarah also noted the disparity not just in the way women are treated in the legal industry or venture capital arena, but a lack of diversity in general – evidenced by the fact that out of a recent survey of U.S. law firms, nearly 75% have launched new programs to address racial injustice.

And yet despite a prolific year and a record number of investments, where the investments were being made was not very diverse.

“What we\’re seeing unfortunately, is that the investments made in female led companies or companies with female founders…has dropped significantly. And that\’s super disappointing. And I don\’t know why, and I\’m sure there\’s a variety of reasons and hypotheses that people are exploring. But this is something we need to work harder at, especially on the female front, in my opinion.”

Squeaky Wheel Gets the Grease

One of things Sarah is proud of is working for a company with not only a female CEO but where over half of the leadership team are females. And that the company as a whole is very diverse and strives to have team members with different backgrounds and different opinions to be as inclusive as possible.

“It\’s something that we make a very conscious effort to try to live by those values and how we look at our team and how we look at the different kinds of policies we rollout…because we really believe that that makes a better culture, a better workplace and a better product for all of our users.”

Sarah continues to lead the charge to change the diversity dynamic and serves as a role model for other young entrepreneurs. Her best piece of advice is don’t be afraid to ask – “the squeaky wheel gets the grease.”

“Don\’t be afraid to shoot for the stars. … Keep being scrappy and just don\’t be afraid to ask. You never know what someone\’s going to say.”

Click here to listen to the podcast with Sarah.

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