Career Profiles: Janine Sickmeyer, NextChapter

This month I had the opportunity to have an exchange with one of the ABA's 2017 Women of Legal, Janine Sickmeyer, the CEO & Founder of NextChapter, a web application for attorneys to prepare, manage and file bankruptcy cases online. As a business leader and entrepreneur, Janine provides strategic vision and direction for NextChapter and is particularly fascinated in the intersection between law and technology in the bankruptcy market. In addition to being selected as one of ABA's Legal Tech Resource Center's Women of Legal Tech 2017, Janine is also a Pledge 1% Women Who Lead of 2017.

I had a few questions for Janine...

- Tell me about your career path, and how you ended up in the legal tech space? What was your interest in the legal tech space?

I started my legal career over ten years ago as a paralegal in foreclosures and creditors' rights but quickly discovered my passion to help debtors on the consumer side. I started a virtual paralegal firm in 2012 preparing bankruptcy documents for attorneys across the U.S and found competitor software to be time-consuming, unreliable and inefficient. I knew there was a need for a cloud-based bankruptcy application and loved new technologies in the legal space so I taught myself to code, built a team of skilled developers and tested the software with attorneys and paralegals while building NextChapter over the next few years. Since NextChapter launched in 2016, we have seen tremendous growth month over month. 

- What made you decide to start a company/organization or take on an alternative career path? Specifically, why did you decide to found NextChapter?

The bankruptcy market was longing for innovation at the time and I was ready to tackle that battle. I have always been an entrepreneurial person but I realized when building NextChapter that legal tech is my calling. Going from a law firm to a legal tech startup is refreshing and exciting! Although there are highs and lows when it comes to startups in general but knowing how to work with attorneys has been essential to the success of NextChapter.

- What advice would you give to current law students or young lawyers interested in working in legal tech, or an alternative career path within law?

Starting a legal tech company or joining one from the ground up requires patience, persistence and energy. Most of the time, you have to wear many hats so be sure to do your research and meet with others in the legal tech field before jumping all in. There are plenty of legal tech meetups and groups designed to help you network with those in the space. 

- What resources would you recommend for learning about the legal tech space?

Books, blogs and podcasts from experienced legal entrepreneurs are the best way to start learning. Some of my favorite resources include:

  • Podcasts: Lawyerist Podcast 
  • Blogs: Law Sites, Lex Tech Review, Associate's Mind, ROSS Legal Tech Corner
  • Books: Venture Deals, Zero to One, Lean In

In addition, attending legal tech conferences will also introduce you to a world of new innovation in the legal tech space. One of the best is ABA TECHSHOW, held every year in the Spring in Chicago, IL.

- What skills are useful to pick up for someone interested in transitioning to the legal tech space?

Being part of a small startup gives you autonomy and freedom but also requires you to learn things you never knew you would. Some of the important skills necessary to work in a legal tech startup include: customer service, online marketing, sales, product management, startup fundraising, business strategy and customer retention among many others.

- On ambiguity and taking the leap into entrepreneurship:

During the first investor meeting I ever had, he looked at my perfectly prepared binder with labeled tabs and spreadsheets of optimistic sales and he asked how I felt about ambiguity. He said all successful entrepreneurs were comfortable with uncertainty. At the time, I wasn't really sure. All of my decisions until that point were made because I wanted them that way, not because something hadn't worked out as planned. As time went on, I discovered I didn't need everything to be calculated to the penny. Sometimes you just have to wing it.

You ride the rollercoaster for the highs and it's all about that moment at the top when you can see above everything else, feel the cool breeze on your face with a knot in your stomach and excitement for the next wave of momentum to keep you going through the lows. That's what it's like to work in a legal tech startup.

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