CEO Spotlight — Sarah Schaaf of Headnote
20/20 foresight.
It’s no less of a pipe-dream than super-speed or invisibility. But those who know startup-life understand the intrigue. The ability to see ahead with confidence. To understand that doing (x) today will cause (y) in 5 years.
We know that AI is enabling better predictions for start-up success, but even still, true clairvoyance likely will remain out of reach for some time. Until then, founders must accept that foresight is inherently foggy.
Few know this better than Sarah Schaaf, who has transformed from big firm litigator to Google attorney to startup entrepreneur. Today, she is the founder and CEO of Headnote, the leading provider of legal billing software in a rapidly-growing SaaS industry.
What Sarah describes as an “anything but linear” journey starts with her upbringing. The daughter of two lawyers, she was destined, on paper at least, for a career in law. She worked at her parents’ law firms growing up, earned her law degree, and then was recruited to join multiple national firms. But after landing a position at Google — a ‘dream company’ for many — she jumped ship.
“I was done marching to the beat of the traditional drum,” she says. “I wanted to change the world, but knew that over time, it wasn’t going to get any easier.”
And thus, Sarah Schaaf the Entrepreneur came to being.
Sarah passionately believes that lawyers (despite the thousands of jokes to the contrary) provide a critical positive service to society. Half of the attorneys in the US are small business owners or individual freelancers. They do the hard work of defending the exploited, righting wrongs, and upholding the rule of law. But few professions suffer under as much administrative burden as legal. Sarah knew there was an opportunity to provide better tools.
From the outside looking in, a total lack of business experience sounds like an entrepreneur’s worst enemy. But what many would consider a disadvantage, Sarah viewed as motivation.
“I rolled up my sleeves. I navigated with a blindfold. I talked to anyone who would talk to me,” she says. The hard work, coupled with her extensive legal expertise, paid off. Headnote flourished and now boasts the fastest growing legal payments network in the US. Who needs business school when you can just work your ass off?
A lot of things went right for Sarah as she transitioned to entrepreneurship, but footnotes exist. She would be the first to attest, being a female CEO in Silicon Valley comes with adversity.
“(Three years ago…) it was almost impossible to get the attention of male entrepreneurs and investors because they didn’t take me seriously,” she says. “I’ve had investors ask about my family planning and health care situations in pitches. Only women hear that kind of stuff.”
Fortunately, in teaching herself the ropes of entrepreneurship, she found herself immersed in a tight-knit network of female CEOs. “I would cold-call powerful female CEOs and they would answer. This amazing network looks out for one-another,” she says. “It changed my life.”
Sarah clarifies that for every female CEO who helped her along the way, there were men who were equally supportive. The community of entrepreneurs fighting for fair opportunity is diverse, and it’s stronger than ever. It’s comprised of people of tolerance and curiosity. It’s comprised of people like Sarah.
Now Sarah is at the other end of the same cold-calls she made not too long ago. If her goal was to break away from the beat of the traditional drum, she has achieved it. She laughs when asked, “How has your lifestyle changed?” Her answer would require an hour (and perhaps a bottle of wine).
Steve Jobs once said, ‘You can’t connect the dots looking forward; you can only connect them looking backward.’ Sarah agrees. “Every part of my path makes so much sense now,” she says.
It took a village of people to support Sarah through this journey — her co-founders (one of whom is her husband Thornton), advisors, investors, customers, employees, and friends. “If I had been a practiced entrepreneur from the start, I wouldn’t have all of these new relationships,” she says. “I would not trade that for the world.” Perhaps 20/20 foresight is not so interesting after all.
