Innovation Blog

Lawyer-turned-Founder Disrupts Immigration Law with AI: Interview with Natalie Holzaepfel


Natalie Holzaepfel, CEO of LegalPilot, is joining the MassChallenge Texas in Austin 2020 program as an Alumni-in-Residence. Natalie participated as a founder in the 2019 MCTX Austin cohort. Natalie is a lawyer-turned-founder that is working to use AI to improve access to legal services. In this Q&A, Natalie shares her story and the revolutionary impact technology and natural language processing is having on legal work, as well as her recommendations to this year’s MCTX Austin cohort on how to make the most of their experience this summer.

Q: Tell me about your startup.

A: Sure! LegalPilot is a startup that makes immigration services more accessible and affordable by utilizing artificial intelligence (AI) to automate the immigration process.


In immigration law, we have three market segments – people seeking employment visas to work in the U.S., people seeking immigration services for family members to enter the U.S., and people who are facing a humanitarian crisis and are seeking asylum. We’ve found traction with providing our services to high-tech U.S. startups that are looking to bring in talent from abroad, but in the long-term we are looking to serve the needs of all three market segments.

Q: How does the core technology of LegalPilot work?

A: Right now, our product uses complex conditional logic to help people prepare the paperwork and documents they need for an immigration filing. Our AI focus is in natural language processing (NLP). NLP has a huge application in the legal field because it can be used to automate legal research – you could say it’s been a breakthrough for legaltech startups. What does NLP look like for immigration services? Say you have a green card case on your desk and you need to answer a question by analyzing similar cases that have already gone through the system – NLP can identify keywords in your query and automatically trace it back to a particular foundation of knowledge to help answer your question. We’re working to use NLP process flows that trace queries back as accurately as a lawyer but at a fraction of the time and cost.

Q: How does your background connect to your current work?

A: I’m a licensed attorney in both California and New York, and I worked on the U.S. Court of Appeals for the Ninth Circuit, as well as at a top ten international law firm, Cleary Gottlieb Stein & Hamilton, and west-coast based law firm Perkins Coie. While I was primarily doing commercial litigation and enforcement work, I also took on pro bono cases. Part of my pro bono caseload included assisting asylees in the United States – some of the most rewarding work in my career. Also, while clerking on the United States Court of Appeals for the Ninth Circuit, which covers federal appeals for the entire West Coast, I witnessed a large volume of immigration cases being appealed. That gave me firsthand access to analyzing the common mistakes that led to an appeal in immigration cases and helped spark the idea that there could be a technological solution to make the efforts of one attorney reach an infinitely larger number of clients.

Q: How has MassChallenge impacted the trajectory of LegalPilot?

A: MassChallenge was one of the best things I did for our company. Because my background prior to LegalPilot was more focused on high-level legal roles than on business development, I had to bridge all those knowledge gaps to launch a successful startup. Joining MassChallenge meant plugging into a great community of founders who were going through the same hurdles that I was facing. MassChallenge helped me quickly learn what it takes to run a successful startup so that I could turn around and execute strategies to scale my company’s value.
Q: As an incoming Alumni-in-Residence, what advice would you give to this year’s cohort of founders?

A: I have two big takeaways from my time at MassChallenge: leverage the experience of those around you and be open to changing directions with your startup idea. Members of this year’s cohort should go to every event and get to know other founders and experts, then ask for a one-on-one follow up to develop the relationship. It is so worth it to put in the extra effort because this is such a unique opportunity to grow and develop. When you get to the customer discovery portion of the program, make sure that you have your ears and eyes open to what your customers are actually saying. Going in I had a certain idea of LegalPilot focusing on family-based immigration cases, but we pivoted to focusing on employment visas because we learned to listen to what problems our customers were actually facing. Be passionate about the why, but listen to others to understand the how, then lean in and build your startup.


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