Women of Legal Tech 2020

Women of Legal Tech: Sarah Schaaf

The Legal Technology Resource Center’s Women of Legal Tech initiative is intended to encourage diversity and celebrate women in legal technology. This initiative launched in 2015 with a list of innovators and leaders in legal technology and with this year’s additions, that list now includes 120 talented and influential women leaders. Every Wednesday, we will be featuring a woman from our class of 2020. This week we have Sarah Schaaf!

Sarah Schaaf is CEO of Headnote.




How did you become involved in legal tech?

I spent the majority of my life working in and around law firms and lawyers. Both of my parents are practicing attorneys and each owned their own firm—our family business was running two independent and very different law firms. I spent many weekends and summers working at these firms in nearly every imaginable context from receptionist to file clerk to legal admin. Eventually, I went to law school and became a lawyer in my own right. I began my career as a litigator at a mid-sized firm in San Francisco in 2008. After a few years, I was recruited by a large national firm in San Francisco and continued to work in litigation but began exploring corporate work as well. Within a year I accepted a role working in Google’s legal department. At Google, I saw how law and technology could combine to make legal operations much more efficient than I had seen in the law firm setting. I decided to leave Google to begin a legaltech company that would help small and medium law firms become more efficient in one of the most important (and often overlooked) parts of their operations—how firms get paid and manage their accounts receivables. I founded Headnote to do just that in 2016.

What projects have you been focused on recently?

I have spent the past year trying to keep up with the substantial growth we’ve experienced as a company. This includes focusing on hiring and recruiting, growing our integration partnerships, and scaling our payment technology. I also started a private group for other legaltech founders located in the Bay Area called Silicon Valley Legal Tech. The group’s mission is to bring together technology companies that are driving innovation in the legal industry but don’t have the reach or resources to keep up with some of their (often outdated) incumbent competitors. We believe that if attorneys and firms have access to the best tech regardless of a company’s competitive moat, we all win.

Is there a legal tech resource of any kind that really helped you when you were starting out in the field?

I think the most helpful thing I’ve found every step of the way is the legaltech community itself. I learn so much for other founders including their mistakes and their successes. I’ve found that most entrepreneurs will give you time and advice if you ask them—you’d be surprised at some of the people that offered to help without knowing me. Most successful founders have had someone help them along the way and they are more than willing to pay it forward. The same goes for me, no matter how busy my schedule may be, I can always find time for other founders.

What technology do you think lawyers could look at in a different way that would benefit society?

Honestly, I think lawyers should start looking at their firm metrics differently. We are fixated on hours billed but what we really need to understand is hours paid. It’s those lost hours that drive up hourly rates and lead to higher prices for our clients. By tracking data points that lead to better business decisions we can provide legal services at a reasonable and efficient price point which can benefit our clients. If the legal industry as a whole was more concerned with business and payment metrics rather than hours billed, firms could operate more efficiently and society at large could benefit from more access to legal services at reasonable rates.

What advice would you give to other women who want to get involved in legal tech?

Find the people that you think you can learn from, seek them out, and ask for their help. Many people are simply afraid to ask for help, but I think men tend to ask for what they want more directly than women. I think the squeaky wheel gets the grease—if you want something, ask for it directly and don’t stop asking. No one will help if they don’t know that you want it.

Give a shout-out to another woman in legal tech who you admire or have learned something from!

I am constantly learning from Maddy Martin at Smith.ai! She has some of the most admirable qualities—she is incredibly direct, honest, loyal, and resourceful. I’ve seen her pull off some incredible partnerships and goals using nothing more than her wits, her courage, and her amazing improvisational skills. If I ever need to be in a foxhole with another woman in legal tech, she’s my gal.

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