#198 - Jacqueline Schafer, CEO of ClearBrief on finding product-market-fit.

Transforming the fairness of our legal system by bringing together the best of people and technology

This podcast interview focuses on product innovation that has the power to make change to the effectiveness and fairness of our justice system. My guest is Jacqueline Schafer, Founder, and CEO of ClearBrief.

Jacqueline Schafer

Jacqueline began her career as a litigation associate at the New York law firm of Paul, Weiss, Rifkind, Wharton, & Garrison, and spent the majority of her career as an Assistant Attorney General in the Washington and Alaska Attorney General’s Offices, where she specialized in appellate practice and complex litigation.

Before joining the startup world, Jacqueline also served as in-house counsel for the national nonprofit Casey Family Programs, where she negotiated agreements with state courts across the country and managed impact litigation. She graduated magna cum laude from the University of Pennsylvania and cum laude from Boston University School of Law.

Today she’s the Founder and CEO of Clearbrief, a legal tech startup that’s on a mission to transform the legal writing process and create a fairer justice system.

And that inspired me – and hence I invited Jacqueline to my podcast. We explore what’s broken in the legal tech market. That the focus is too much on the process, and not on the outcome – a more just legal system. Jacqueline shares her vision for the Justice system and how she’s carefully architecting a product that’s both sticky for its users, has strong network effects, and an ability to create a fairer justice system for all of us. She talks about the biggest hurdles she had to overcome – and what’s been critical in her eyes to create a remarkable software business that has staying power.

Here are some of her quotes:

“I was doing a pro bono asylum case, representing a woman and her toddler, and in those cases, it really comes down to a final hearing, and it’s life or death for these individuals. And so, there was a moment at that hearing where I saw the judge was not inclined to find in favor of my clients. But I pointed him to a sentence in my brief, which was a 50-page intense legal document. 

That was what convinced the judge. He looked at the evidence, he looked at that report, in the context of my argument, and we won the case.” 

During this interview, you will learn four things:

  1. Why you should develop a strong evidence skill and avoid taking shortcuts in finding product-market-fit.
  2. How to build a product that has staying power with its core users and put a smile on their face – every single day.
  3. Why it’s key to connect the dots to the larger impacts we’re aspiring to understand the true problem we’re solving.
  4. How to introduce meaningful change to an industry that’s not changed in decades.

For more information about the guest from this week:


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About the author

Sales Pitch

Ton Dobbe is a former B2B software product marketer who's on a mission to save mission-driven SaaS CEOs from the stress of 'not enough' traction. He's the author of The Remarkable Effect, the host of the Tech-Entrepreneur on a Mission podcast, and writes a daily newsletter on the secrets to mastering predictable traction.