Sarah Schaaf, chief executive officer, Headnote

 

There's a shortage of women in science, technology, engineering and math. And there's still a 17 percent gender gap in pay—across the board—in all of legal (18 percent at Big Law). But within the legal technology community are many women with thriving careers. Monica Bay recently interviewed Sarah Schaaf. Schaaf is chief executive officer at Headnote, a venture-backed legal tech company based in San Francisco.

Education: University of Arizona for my B.A. in Sociology with a minor in Spanish, class of 2003. I then went on to follow in the footsteps of my attorney parents by attending Loyola University Chicago School of Law for my J.D., class of 2008. I like to consider myself a “reformed” attorney, but yes, I am a lawyer admitted in California.

In school, did you consider a career in science, technology, engineering or math? I didn't. I always wanted to be a litigator. I never imagined that my legal career would lead me to a job in tech, but I love (almost) every minute of it.

First paid job: Working as a poodle-skirt clad hostess at a 1950's diner-themed restaurant. The best part was the free milkshakes.

Current job: Chief executive officer at Headnote, an early-stage venture-backed legal tech company in San Francisco. Headnote is a secure, easy way for law firms to get paid online compliantly. It's as easy to use as PayPal, but made specifically for lawyers' rules regarding online payment compliance. I dislike that legal is the last big industry that still uses paper check as our main form of payment. I pay everyone online from my doctor to my pool guy, so why do I need to find my checkbook to pay my attorney?

Our goal is to offer firms of any size an accessible and affordable way to add online payments into their workflow, so they realize more revenue and improve collection speed. We pay attention to our user experience (unlike many legal software on the market) because we want your clients to have a convenient and modern payment experience. Every contact with a client is important, from the first time they call your firm to the last time they make a payment. Every touch point is an opportunity for a firm to offer elevated customer service and payment is no exception.

Your “first seat at the table” and how it influenced you: I took the California Bar in July 2008. While waiting for results (I passed), the financial crisis of 2007-2008 arrived, and the legal industry was no exception. I thought I would be without work, but I quickly got a job with a mid-sized firm in S.F. Within a few weeks, they had me going out on depositions! After observing a few, it was my turn to lead. I was terrified! I over-prepared and ended up crushing it. It taught me that there is no substitute for preparation. I think great on my feet, but the extra confidence I get from feeling prepared makes me unstoppable.

First obstacle and how you overcame it: Early in my career I worked closely with a partner who decided to make me prove my work ethic (or at least that's what I deduced). One evening I was on my way home from a deposition that had run late. He called my around 8 p.m. to tell me there was a brief that needed to be drafted and ready to file by the next morning.

I was exhausted, but went back to the office and grinded it out. The next morning he didn't have the brief filed—it turned out it wasn't even due. He just wanted to see if I would put in the work. I was furious. But I didn't want to give him the satisfaction of knowing he had gotten to me. So I just kept working hard and slowly made my way off all of his cases and onto teams with attorneys that I admired. I played his game better than he did, and figured out a way to get where I wanted with or without his support. In the end, he came around and I gained his respect, but it was an interesting early lesson in the importance of well-planned strategy.

Most flagrant sexism you personally encountered and how you address it? When I was fundraising I had a few experiences. When I was raising my seed round, I was a female CEO in my mid-30s with my husband as a co-founder—and a toddler at home. At one pitch meeting, a male investment partner asked me straight out about my family planning and childcare. I was shocked. I couldn't imagine him ever asking my husband or a male CEO the same question. I answered that I wasn't sure and ended the meeting soon thereafter. I decided that I wouldn't have taken his money even if he wanted to invest. I choose whom to work with and refuse to have my sex, age or family seen as a liability. (I gave birth to my daughter five months ago.)

Secret to your success: Work hard, be yourself, ask others for help when you need it.

Dress codes? This is a funny question given that I work in the land of the hoodie. In the San Francisco Bay Area almost anything goes. On my first day at Google, I showed up in a casual suit dress—I stuck out because I was clearly overdressed, and I never wore it to work again. I always try to dress professionally but comfortably. I always want to look lawyerly, but now I try to look like a tech leader as well.

Advice for young women: Just don't let yourself be held back by anything. You really can do anything you set your mind to, with hard work, resourcefulness and resilience. People might tell you it's a long shot, but don't let that stop you: prove them wrong.

Five favorite technology tools:

  • Slack: My team's preferred method of communicating, it makes team collaboration a breeze.
  • G Suite: Best email and calendaring platform; I could not live without Docs, Slides and Sheets.
  • DocSend: Gives analytics on docs you email so you can see exactly who reads it, for how long, how long they spend on particular pages, etc.
  • Venmo: Simple payment tool—this makes it easy to pay and get paid by friends instantly.
  • Invision: Doing user experience work is a favorite part of my job; this allows me to work with my designers and engineers to make my ideas come to life before my eyes.

Book that inspired you? The Hard Thing About Hard Things, by Ben Horowitz. Reminds me that no matter how big some of my business challenges seem, others have dealt with far worse before me and came out on top.

Favorite vacation venue: Hanalei, Hawaii. So peaceful and not too developed. I love how the mountains feel like they are coming right out of the ocean.

Your mantra: Yes, I can. I believe can is such a powerful word.

Favorite quote: “Go confidently in the direction of your dreams—live the life you've imagined!” — Henry David Thoreau

 

Monica Bay is a Fellow at CodeX: The Stanford Center for Legal Informatics. She is a columnist for Legaltech News and a freelance journalist (Alchemizing Law LLC). She is a member of the California Bar. In 2015, she retired from ALM (Editor-in-Chief at Law Technology News). She lives in Connecticut but can get to Yankee Stadium in two hours.