UniCourt Influencer Q&A with Jonathan Pyle of Philadelphia Legal Assistance

As a litigation associate at a large law firm, Jonathan Pyle realized the legal industry desperately needed automation solutions, so he spent his spare time creating tools to fill the technology gaps that led lawyers to waste hours of their time every day. These projects ultimately led him to conceive Docassemble, a “guided interview” platform that generates solutions to common legal problems consumers face.

“No one else seemed to be going in that direction,” Pyle says, “so I did.” This, precisely, is Pyle’s philosophy on problems that sit at the intersection of law and technology: if no one else has come up with a solution, he will.

We were thrilled to sit down with Jonathan to learn more about his background, his career path, and the problems that drove him to create Docassemble.

UniCourt: Tell us your story. What’s your background, and what led you to the work you are doing now?

Jonathan Pyle: After law school, I worked as a litigation associate at a big firm and enjoyed it, but I couldn’t stop myself from spending part of my time computer programming. I had taught myself computer programming when I was a kid, and as a lawyer who knew how to code, I didn’t like wasting my time doing dull tasks that I knew could be automated. So I spent my spare time writing tools for docket scraping, cleaning up text scanned with optical character recognition (OCR), and building web applications for document review. I was filling technology gaps for which off-the-shelf software didn’t exist.

The law firm partner track wasn’t for me, and I ended up working at Philadelphia Legal Assistance, which provides free legal assistance to low-income people with civil matters. I found that the legal aid field is more technologically forward-thinking than large law firms, despite a relative lack of resources. Legal aid organizations are willing to try new things, like providing meaningful legal services entirely over the internet.

At PLA, my official position is Compliance Officer, but I also work on a number of grant projects at the intersection of law and technology.

UC: What is Docassemble, and how does it work?

JP: Docassemble is an open-source software project that I created during my nights and weekends. It is a technology platform for creating mobile-friendly web applications that ask a question at a time to gather facts from the user, apply legal rules to the facts, and produce an end result such as a legal pleading or advice. So if you want to create the “TurboTax for x,” Docassemble makes it easier for you to do that. It is a “guided interview” platform similar in purpose to Neota Logic, Contract Express, and HotDocs, but with an open-source flavor.

UC: What inspired you to create Docassemble and make it open source? Was there a particular moment or problem that motivated you to seek a solution, or is this a project you’ve always wanted to explore?

JP: I once attended a meeting of legal aid document assembly developers who spent half an hour complaining about how it was impossible with the leading software platform to do a “nested loop,” for example to ask a user for a list of all their family members, and then for each family member, ask about all of their children. I thought, “this is insane, I have been writing nested loops since I was 12.” The software platforms were optimized for beginners, but people with extensive experience were using the platform all day long. These systems promised to allow attorneys to write code “without writing code,” but what they were really doing was putting up brick walls and preventing capable people from doing things that are easy to do with code.

I thought that the legal-tech industry had plenty of “easy” tools, but really needed an automation platform that followed the principles of the open-source software industry: customizability, modularity, reusability, and openness. I wanted to see legal-tech on GitHub and Stack Overflow. Nobody else seemed to be going in that direction, so I did.

UC: How do you think the legal industry as a whole can benefit from an increase in open-source software?

JP: Technology companies have embraced the open-source software movement over the past 20 years, and it’s not because they aren’t competitive; they are still protective of their “secret sauce” intellectual property.  But they recognize that contributions to the open source community are a rising tide that lifts all boats. Open-source platforms make engineers’ jobs easier, so they can concentrate on the things that are specific to the business.

I think the legal industry is due for a technological renaissance. Instead of paying lots of money to vendors who deliver off-the-shelf software we don’t like and that doesn’t do exactly what we want, we could build the tools that meet our needs. People think computer programming requires a genius brain and lots of money, but if there is an open-source community, it’s more like building with blocks. For example, if I want some code that conjugates verbs, I don’t start from scratch, I just do a Google search, find a software package that conjugates verbs, install it, and write a couple of lines of code to use it. It takes minutes, not months.

UC: How do you think that open-source systems like Docassemble increase access to justice?

JP: For example, if you are a low-income person who would benefit from filing for bankruptcy, you are expected to spend $2,000 on a lawyer to help you file a bankruptcy petition. People who are heavily in debt don’t have that kind of money. That’s an access to justice problem. A few years ago, a non-profit called Upsolve came along and used technology in more sophisticated ways than any previous company had done, in order to automate the bankruptcy process as much as possible while maintaining a human component and providing quality control. With a small staff, Upsolve has discharged over $200 million in debt without charging clients any fees. They were able to do this with open-source software, including Docassemble.

My hope is that Docassemble will enable people from all parts of the legal industry to create game-changing applications like Upsolve that drastically reduce the cost of legal services while maintaining or increasing quality.

UC: What are some of your favorite sayings? Do you have any examples of how you’ve seen those sayings come to life in your personal or professional lives?

JP: One of my favorite sayings is “there are only three numbers: zero, one, and n.” I always think about how things can be generalized and limits can be avoided. For example, one of the features that people want in a guided interview system is the ability to customize the color scheme on the page. I didn’t solve this problem by creating four “themes” that users could choose from. Instead, I incorporated the Bootstrap user interface system, so that people could find a theme on the internet and use it in Docassemble, or find a Bootstrap theme-building web site and create their own custom color scheme. This solution is more complicated, but provides the user with more control.

UC: What are your goals for the coming year? What projects are you working on? Are there any upcoming events in the legal tech or legal innovation space we should be aware of?

JP: I would like to expand the features of Docassemble that support mediation and on-line court processes. I hope COVID-19 catalyzes courts to do more things online while increasing access and effectiveness. I don’t have all the answers, but I think there is a lot we could do to make the court process better for litigants using high-quality educational materials and sophisticated guided interview tools that access court dockets and documents through APIs (Application Program Interfaces).

One project I help support at Philadelphia Legal Assistance is a remote hotline staffed by volunteer attorneys and law students who help Pennsylvania residents apply for unemployment compensation. On the technology side, it’s a mash-up of Google Forms for volunteer sign-up, Twilio TaskRouter for the telephony, Docassemble for tracking information and assembling documents, Google Sheets and Google Drive for storing data, Sendgrid for sending email, and Mail-a-Letter for sending snail mail.

In June, I will co-host the third annual, and first virtual, Docassemble conference. “Docacon 2020” will take the form of a series of trainings with a beginner track and an advanced track, so that people who want to learn more about Docassemble can learn from interactive classes rather than by reading on-line documentation.

UC: Where can we learn more about you and your work?

JP: People can check out Philadelphia Legal Assistance at https://philalegal.org and learn about Docassemble at https://docassemble.org. Docassemble has a very active Slack group, which is open to the public. Information about our annual conference can be found at https://docacon.com.

A Technological Renaissance

As Jonathan notes, lawyers tend to think that programming requires “a genius brain and lots of money.” However, the creation of an open source community assuages shared concerns over the practical implementation of technological tools. By equipping the legal industry with tools that reduce the cost of legal services while maintaining the highest quality, Docassemble is paving that path. We are excited to watch its features expand into online court processes and beyond, and will be watching Jonathan’s progress closely as he develops other projects that work to close the access to justice gap.

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