Robert Ambrogi Blog
Content is the raw material of generative AI, so it only makes sense that an AI-driven contract automation platform would want to acquire what is said to be the world’s largest database of contracts and clauses.
That is exactly what happened today as SimpleDocs, a company with an AI contract drafting, redlining and review platform, has acquired Law Insider, which claims to be home to 5 million contracts and 20 million clauses spanning more than 50 languages.
“By uniting industry-leading legal AI with the world’s largest contract and clause database, we’re building toward a future where every draft is grounded in precedent, every review is benchmarked against market standards, and every automation reflects precisely configured negotiation positions,” said Preston Clark, SimpleDocs’ CEO and cofounder of both companies.
“The result is contract automation that delivers unmatched precision, quality, and ROI.”
The acquisition creates one of the largest global communities of contract professionals, the company says, with millions of monthly users and more than 12,000 combined customers.
[Pictured above: Electra Japonas, Preston Clark, Jordan Trevino and Ali Waqar.]
A Long-Term Vision
The acquisition represents the culmination of a long-term strategy for Clark, who started Law Insider in 2009 with the vision that its public contract data would eventually become a foundation for something greater in legal tech.
With the rise of legal AI and its application to contracts, he saw the opportunity in 2023 to launch SimpleDocs as a “sister business” focused on contract automation for in-house teams and law firms.
“It was always about getting to this day,” Clark told me in an interview for my LawNext podcast that will air next week. “It was always about bringing them together.”
Although the two companies shared Clark as a cofounder, they operated as separate and distinct businesses, with separate executive and product teams.
That changed last March, when Law Insider launched an AI powered contract drafting, review and redlining tool for its global community of 1.2 million registered users, which it developed in partnership with SimpleDocs and based on its technology.
According to Clark, the first 90 days of that partnership “exceeded all expectations,” seeing adoption by more than 5,000 active users across 20 countries and validating both the channel market fit and time to value. That success made the decision to merge inevitable, he said.
Precedent-Based AI
In announcing the acquisition, SimpleDocs positions it as “setting a new standard for contract automation.” That standard, Clark told me in our LawNext interview, centers on precision and configuration, addressing what he sees as a gap between generic AI tools and truly valuable legal AI.
“The difference between well performing or well tailored legal AI and just general Claude, ChatGPT, et cetera, is how much it is configured to your exact use case,” Clark said. This means configured playbooks and workflows that mirror exact processes – what to reject, what to accept, how to issue spot, and what standard comments to use.
But SimpleDocs goes beyond even just client-specific configuration, Clark said. By integrating Law Insider’s contract precedent database, the platform can now benchmark against market standards – identifying missing clauses, flagging non-standard terms, and comparing language to what is typical in the industry.
“The idea that the AI can now do that automatically for them alongside Microsoft Word or in the browser environment is very powerful,” Clark said. When he discussed this capability with customers during pre-acquisition conversations, he said, their response was an immediate head nod.
Quality Over Quantity
Clark acknowledged that simply having a massive collection of data does not automatically translate to having the best data. The key, he explained, is adding “a layer of intelligence and intent” to filter the data appropriately.
“There’s still work to be done there,” Clark said, noting that SimpleDocs will now focus on filtering Law Insider’s data with greater precision to create actionable insights about what is truly market standard – not just what occurs frequently.
Law Insider has spent years developing approximations of standard language for different agreement types and clauses. Now the task is to refine that with even more intent to make the data more useful within SimpleDocs’ AI platform, he told me.
How It Works in Practice
The acquisition will result in a combined offering that will operate in two environments: a web-based drafting tool and a Microsoft Word add-in (the company’s existing SimpleAI product) for reviewing and redlining.
In the browser-based drafting environment, users will be able to compare the language they are generating against market standards at both the contract and clause level. The system will show what clauses are missing and how the included clauses compare to market norms.
Inside Microsoft Word, when reviewing third-party agreements, users will benefit from two layers of analysis: their own configured playbook defending internal positions, plus precedent-based scoring at the clause and contract level with proposed changes.
“If this agreement is so far out of bounds or the counterparty has surreptitiously tried to inject something in here that I didn’t even know to be checking for because it’s so inappropriate to be in this agreement, the precedent of Law Insider will catch it, will flag it, and will propose a change against it,” Clark explained.
Legal Engineering
Last year, Law Insider acquired oneNDA, an organization that had developed an open source contract standard for non-disclosure agreements, and last February, it launched oneSaaS, a standardized template for cloud services agreements.
After that acquisition, the founder of oneNDA, Electra Japonas, joined Law Insider as chief legal officer, and she now moves into that role for the combined companies. She will oversee the expansion of the company’s legal engineering function – including the design of playbooks and workflows to enhance contract automation for corporate legal teams.
See my interview with Japonas about the acquisition:
This legal engineering function will be critical as the company moves forward, Clark said, because, despite advances in AI, proper implementation still requires significant effort.
“If any vendor is saying that you just upload a document and your playbook is completely set up and reviews perfectly, it’s categorically and inherently imperfect,” he said.
In addition to Japonas, other members of the executive leadership are Jordan Trevino, cofounder of SimpleDocs and chief technology officer, and Ali Waqar, also a cofounder of SimpleDocs and chief operating officer. Clark remains CEO.
Market Positioning
The company says that SimpleDocs is one of the fastest-growing legal AI platforms and delivers contract software to thousands of legal teams worldwide. Its flagship products, SimpleAI and the SimpleAI Repository, are used by major public and multinational companies, including Coty, PwC, BitGo and dbt Labs.
Clark said Law Insider represents one of the largest global communities of contract professionals, with millions of monthly users and more than 12,000 combined customers.
Clark sees his primary competitors as Spellbook and Robin AI, and he aims to establish SimpleDocs as “the de facto third player in the market.”
Clark believes the legal AI contract market represents a rare “greenfield moment” – a new category where there’s available budget, C-level urgency, and everyone is buying for the first time.
Remaining Independent
Both Law Insider and SimpleDocs have been bootstrapped and profitable. Asked whether the company plans to pursue outside investment in order to scale, Clark expressed hope that it will not need to.
“I think that we get to play by different rules if we don’t raise capital,” he said. “We get to pursue different outcomes. We get to price more competitively. We get to stay more focused on the use cases that are profitable and that are making our customers the happiest.”
While acknowledging that market forces might eventually necessitate outside capital, Clark said he would rather not and believes they can build a major, well-managed business with their own capital.
Looking Ahead
Customers can expect to see the fruits of this acquisition soon, Clark told me. Some features enabled by the combined engineering and product teams will launch incrementally in the coming weeks. The deeper “what’s market” benchmarking features that require sophisticated filtering of Law Insider’s database are targeted for this quarter or the next, Clark said.
The Law Insider website and database will continue to be publicly available through lawinsider.com, with existing free users and paying subscribers able to continue their current plans and gain access to optional AI upgrades, including both browser-based and Microsoft Word-integrated drafting and review tools powered by SimpleDocs.
Clark sees this as just the beginning. Beyond the immediate contract drafting and review focus, he envisions addressing adjacent needs around obligation management, alerts, routing, self-serve access, and approval flows – essentially reimagining contract lifecycle management as “much more unbundled and much more AI native.”
“I’m just excited to show the world how hard we’re working and how much our customers are influencing the roadmap,” Clark said. “I can’t wait to have a conversation about this a year from now when we see our NPS score and our retention numbers, when we see our adoption curve.”