The End of AI Pioneers in Law + A New Beginning – The Artificial Lawyer

“Is this the end of the early legal AI pioneers?” is the question one might ask as the ink dries on Evisort’s deal to sell to Workday. Artificial lawyer looks at the extent to which the market has consolidated as legal tech M&A continues across the sector, and asks whether new AI pioneers in legal services will experience the same outcome?

At least for this site, “legal AI” as a topic really took off in the 2010s, gaining wider market attention around 2015/2016 when a growing number of startups emerged, using machine learning and earlier versions of natural language processing. Then one by one, some fairly quickly, others only recently, were acquired.

Here are some of them:

• RAWN – one of the early pioneers of ML/NLP in the legal industry, sold to iManage in 2017
• eBrevia – a very early pioneer of contract analysis, sold to Donnelly Financial in 2018 – but recently relaunched as an independent company. One of its co-founders, Ned Gannon, also created a new company focused on internal needs, Coheso.
• Kira Systems – Contract Analysis – Sold to Litera in 2021, which gave birth to Zuva, a new independent company.
• Stamping software – Contract analysis, primarily for enterprises, sold to DocuSign in 2020, reportedly for $188 million in cash. After that deal, several key team members left the company and are working on other AI-related projects, such as Jim Wagner created The Contract Network.
• Leverton – German legal tech and proptech pioneer focused on AI contract analysis, sold to MRI in 2019. The company had a rocky road and was sold shortly after launch.
• RFRNZ – also a German AI legal services company that started early but closed in 2021 due to lack of demand from lawyers.
• (ROSS Interview (—was a pioneer in the application of ML/NLP to case law research. I didn’t make the sale, but I ran into some… er, how do you put it… “legal issues” with Thomson Reuters in 2020. But ROSS really captured the imagination of a lot of lawyers and did a lot of work to raise awareness of what legal AI can do.)
• CONFUSE – Another early pioneer of AI research, Ravel was sold to LexisNexis shortly after it was spotted in 2017. This transaction followed LexisNexis’ purchase LexMachina in 2015 – yes, that early – a company that really, really quickly started using ML/NLP for legal research.
• Anticipation – a small but innovative contract analytics startup founded by Dan Katz, sold to law firm Elevate in 2018. Katz is currently working hard on genAI as part of a new venture.
• Della AI – rather the second wave of legal AI companies, also focused on contract analysis, sold in 2022 to Wolters Kluwer.
• Own technologies – also part of that second wave, also focused on contract AI, but not just legal. It had Goldman Sachs as an investor. Sold to CLM Sirion this year (2024).
• Case text – another legal research pioneer, sold to Thomson Reuters for $650m in 2023. Started out in ML/NLP, but unlike many others quickly saw future value in LLM, and when ChatGPT came along, did a ton of work with genAI.
• Cover – although it was seen as a CLM company, it was really a contract analytics company that was founded in 2016 at Harvard and could have gone in many directions but followed CLM. Workday announced this week that it would buy the company.

There are others, including some that shone brightly and disappeared just as quickly. But you’ve probably heard of the ones above. And they all have a lot in common: They all used machine learning technology, to a greater or lesser extent, which predated generative AI. Some later used genAI as well, but that wasn’t the technology they were based on.

Besides, we also saw Tim PullanFounder and CEO of ThoughtRiver, which really explored how ML/NLP could be used to analyze contracts for risk and is aimed primarily at in-house legal teams, has stepped down from the top role. Although the company is still in business.

And it’s interesting to see how many of these early founders have gone on to start new companies in legal AI, like Ned Gannon, Noah Waisberg, and Jim Wagner. So while one company they helped build has been sold, that’s not the end of their startup journey.

Standing on the shoulders of giants

Some founders start a company with the intention of selling as soon as possible. Others see their startup as the beginning of a lifelong journey and hope to build something big. In reality, due to outside investment, most startups sell (or cease trading) after a few years, and very few survive beyond 10 years; in fact, even seven years is a good number. So all of the above is natural.

What this really means for this site is that we are really coming to the end of the first wave of pioneers who saw AI as an opportunity not only to build a business, but also to change the way the legal world works.

As they say, we all stand on the shoulders of giants, because there is always someone who paved the way before we arrived. In this case, the generative AI companies that are now growing and multiplying can be seen as third wave of legal AI businessesbut based on a new type of technology.

They, too, are benefiting from the tremendous work done by those who came before them, as the first wave of AI companies in the legal industry helped familiarize the market with the concept of using software not just as a basic tool or information storage system, but also to actually do the work of a lawyer: change the legal means of production. And that remains the main goal.

Furthermore, if history repeats itself – and it seems likely – in a few years Artificial Lawyer will write an article about where all the legal genAI pioneers went. Company X was acquired by a non-legal conglomerate. Companies Y and Z were acquired by one of the Big Two. Companies A and B went bankrupt or stopped trading. Or maybe one or two will simply continue on and become huge companies that dominate their market segments. And so on. The cycle repeats.

And that’s the amazing thing about legal tech. There’s so much energy there. So much dynamism – just think of all the companies above. Now think of the growing number of new ones, from Harvey to Ley, Robin AI and many more. It just keeps coming…!

To the first pioneers, Artificial Lawyer pays tribute. To the new generation, this site says: good luck and may the gods of legal AI always be on your side!