Two companies that legal tech pioneer Preston Clark helped to create: SimpleDocs and Law Insider, have merged together, with the former buying the latter. This combines legal AI skills, especially around contract needs, with a huge contract library.
Law Insider has a library of more than 5 million contracts and 20 million clauses across 50+ languages. While SimpleDocs is a legal AI platform, delivering AI-powered contract software to legal teams worldwide. The deal therefore makes a lot of sense, especially given Clark’s close involvement with both already.
AL asked Clark about the deal.
Can you explain what part you have played in both companies?
I conceived the idea for Law Insider in 2010 (2 years out of law school) originally as a blog relating to the business of law, then shortly thereafter as a contract database after watching Rocket Lawyer and LegalZoom amass large libraries of sample contracts.
I brought on 2 technical co-founders in 2013 (Dylan Myers and Dmytro Sadovnych). Until 2019 Law Insider was a free database project that generated zero revenue. 3 co-founders, no employees, no customers but millions of monthly users. We introduced a premium subscription model for advanced access to the database in January 2019 and have been profitable ever since.
Although I’ve acted as president and co-founder of the business, I’ve never taken a salary and maintained it as a side project while building and scaling numerous other SaaS businesses as both founder and executive. I’ve been part of 7 acquisitions over the past 12 years for venture backed and private equity owned businesses including LawRoom, EVERFI, and Even.com.
SimpleDocs was co-founded by me and 2 (different) technical co-founders (Ali Waqar and Jordan Trevino) in early 2023.
Do you already therefore own both companies?
I’ve held significant equity in both cap tables since inception. And now maintain significant equity in the combined cap table.
How many staff do each of these have?
SimpleDocs: 15
Law Insider: 18
Is anyone exiting as part of this?
No. We’re bringing everyone along. Roles will change but all existing team members will remain.
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With the acquisition, Law Insider’s Chief Legal Officer, Electra Japonas, joins the executive leadership team of the combined company. As you know, she has pioneered contract standards and was the founder of oneNDA. She will oversee the expansion of the company’s legal engineering function a discipline dedicated to designing configurable playbooks and workflows that enable legal teams to achieve ROI-positive contract automation, they said.
Japonas concluded: ‘Now, combined with SimpleDocs, we can take the next step—creating tools that deliver real-world contract precedent and adapt to how each team works. From benchmarking and What’s Market analysis to playbooks and red-flag reviews, we’re making AI not just powerful, but practical.’
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Legal Innovators Conferences in London and New York – November ’25
If you’d like to stay ahead of the legal AI curve then come along to Legal Innovators New York, Nov 19 + 20 and also, Legal Innovators UK – Nov 4 + 5 + 6, where the brightest minds will be sharing their insights on where we are now and where we are heading.
Legal Innovators UK arrives first, with: Law Firm Day on Nov 4th, then Inhouse Day, on the 5th, and then our new Litigation Day on the 6th.
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Please get in contact with them if you’d like to take part.
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