State of Document Automation

by Monday 27th April, 2020Solutions0 comments


State of Document Automation image scaled e1588350128600

Document automation and assembly has been one of the tools in the tech-savvy lawyer’s toolkit for nearly three decades. HotDocs, Contract Express, and Exari (now Coupa) have been the top three contenders, with HotDocs arguably commanding the marketshare among law firms. In recent years, however, the market is shifting. Each of the big three were acquired by parent companies: Contract Express by Thompson Reuters, Exari by Coupa, and HotDocs by AbacusNext. How the new parent companies have treated their acquisitions has shifted the marketshare among the big three and given “upstarts” in the document automation space opportunities for growth. These new offerings have been able to grab a bit of the market pie, and even promise more functionality out of the box than the legacy contenders.

Who are these enterprising new players? Let me focus on a few that I’ve come across recently:

  • XpressDox
  • Templafy
  • Docassemble and its offspring, Documate and Community.Lawyer
  • Knackly


This one is not so much an upstart as a longtime competitor to HotDocs who now has a chance to outstrip them. XpressDox hails from South Africa and provides many of the same features that HotDocs users have grown to love over the years, and then some. The interface and scripting is similar to HotDocs, but XpressDox has worked out the Cloud functionality such that they have Cloud subscription models that have feature parity with their desktop offerings. It appears to be macro-based still, but it integrates with databases, web services, and other APIs easily. And it can break the four-level limit for embedded loops that HotDocs has! That’s a big plus for me!


Founded in 2014, Templafy has fast become a big player in the document automation and assembly area. Not exclusively focused on the legal field, Templafy’s customer reach extends to all types of businesses: legal, financial, insurance. etc. They promise to connect the data in your organization with your templates in a seamless, accurate process, using intelligent automation. Basically, all things document creation would start from a central admin location. From there, people in your organization can start the document creation process and access the assets necessary for the documents they are assembling.

Templafy also has modules you can add to the Admin piece. From a template developer perspective, I find the library, dynamics, and email signature manager particularly attractive. Not only that, they appear to have moved away from the macro model of document automation and assembly and toward one of accounting for what you need in the document (the parts) and then building it with the assembled information in it.

I will definitely be watching them and learning more about them.


Docassemble is a free, open-source expert system for guided interviews and document assembly. It combines Python, YAML, and Markdown (all languages not going away any time soon) into a powerful and scalable document automation platform. Born out of the “Access to Justice” world, Docassemble’s system promises to be the base for many document automation possibilities now and in the future. IMHO, Jonathan Pyle, the creator of Docassemble, is a candidate for Sainthood for his tireless dedication to improving and expanding upon his platform, and not charging anything for it. Here is a list of some awesome features:

  • Word or PDF templates
  • Touchscreen signatures
  • SMS (text message) interviews
  • Multiuser, develop applications that involve more than one user
  • Extensible, with the power of Python
  • Secure server-side encryption, two-factor authentication, document redaction
  • Third-party application integrations using the API
  • Responsive-design interviews that look modern, fresh, and can be completed on your phone, tablet, laptop, or desktop

If you don’t have a technical background, Docassemble can appear to be intimidating. But the truth is that it doesn’t take much to get going with basic interviews. The YAML (“Yet Another Markup Language”) file structure is pretty straightforward, and Markdown is just a way to format your text in the YAML file. Markdown is very easy to get up to speed on. Python is also known for its being very approachable for beginning programmers, but it’s not absolutely necessary to know Python beyond the basic IF-logic conditioning. When you have set up your server and installed Docassemble on it, you will find that Jonathan has provided a playground area with many examples of how to create your YAML files. And the Slack community is great! So you’re in good hands.


If you find that learning Docassemble takes too much time, but you want to jump-start using its functionality, then I recommend checking out Documate.

The team at Documate have built an intuitive, clean, modern interface on top of Docassemble that allows a user to build an interview and connect documents to it, whether DOCX or PDF. Creating an interview is as easy as building a survey with SurveyMonkey. Documate also provides you with a Word add-in that allows you to place the variables you’ve created in the interview into your Word document. If you’re developing a PDF document, they have a PDF tool that prepares the PDF for you to attach variable fields to. And most recently, Documate has released a data manager tool that provides the equivalent of HotDocs “answer files” so that you can take your data with you to the next assembly. Because it’s cloud-based, it’s also OS agnostic, so you can develop templates on a Mac or PC.

Documate is a subscription service that includes the template development tool, the price of the server hosting, and 24/7 customer service that is exceptional, going over and beyond expectations.


Like Documate, Community.Lawyer is a platform that gives you the benefits of Docassemble while freeing you of the need to know how to write the YAML files and the Python code. Community.Lawyer encourages enterprising attorneys to create apps (document automation assemblies) for anyone to use, including their own clients and other attorneys. These can be monetized behind a paywall, and they integrate with Stripe, LawPay, Clio, Google, and Zapier.

Community.Lawyer is a subscription model with a generous free tier that allows you to test your apps out before committing to a tier that offers more features for a monthly or annual fee.

Whether you opt for Documate or Community.Lawyer, both have strong Slack communities that are very responsive and helpful. You’re never alone in the Docassemble world!


The final new contender is Knackly, which was born out of frustration with the limitations of HotDocs and a desire to overcome those with a different approach to document automation. The basic premise is that you have data and you want to use a tool that processes that data and outputs a document. So there is a seamless connection between data you’ve already entered somewhere and the tool you’re using to process it. (“Of course!” you say, but it’s evident that legacy solutions have been anything but seamless.)

I’m still learning about Knackly, but here are the features that stand out to me so far:

  • Clean, modern, cloud-based interface
  • More than four-level limit for embedded loops
  • PC and Mac Compatibility
  • External client interviews
  • Easy API integration
  • HotDocs to Knackly conversion

Document Automation Is Not Dead

As I discussed in a recent post, document automation can help you scale up your practice, compete in the legal marketplace, and reduce the risk of errors. It’s can be an important part of your legal practice, and in the marketplace, the concept is far from dead.

While legacy solutions to document automation were the standard to beat in the past, I recommend checking out these newcomers to see what would fit best for your practice. It’s no secret nowadays that the legacy document automation solutions often fail to provide the functionality needed to compete in the 21st century, so if you’re caught in their vice, then there’s no greater time than now to explore other options.

What document automation solution do you use? Are there any listed here that you would like to know more about?


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