• Cooley is joining a sudden rush of law firms creating their own AI technology, with help from Legora.
• Cooley Go Lab is an online portal built to help startups with routine contract review and drafting.
• The portal will be available exclusively to founders in Y Combinator's summer cohort to start.

Law firms know more clients are asking chatbots for advice before ever calling a lawyer. So legal giant Cooley is building technology that it hopes founders will use instead.

Cooley plans to give select startups access to Cooley Go Lab, an online portal where founders can upload files and ask questions about their documents, Matt Bartus, global cochair of Cooley's emerging companies and venture capital practice, told Business Insider.

To build it, Cooley teamed up with Legora, a fast-growing legal technology startup that sells to law firms and corporate legal departments. Last year, Legora entered a new line of business with what it calls "portals" — white-labeled workspaces where law firms and their clients can work together on legal matters.

Cooley Go Lab is aimed at catching a common startup problem early, Bartus said. Founders often handle routine contracts themselves to avoid outside counsel's hourly rates. That can leave startups with a trail of messy agreements that their first in-house lawyer has to unwind later.

Legora founder Max Junestrand knows the problem well. When he started the company at age 23, he said he used an early version of ChatGPT to rewrite contracts. Junestrand, a software engineer, not a lawyer, said he let some early contracts include an unlimited liability clause — a provision that can leave a company exposed to damages far beyond the value of the deal.

"When our general counsel started, she freaked out," he said.

Cooley is now trying to give the next crop of founders a way to use artificial intelligence to move faster, but with a law firm's guardrails around it.

Cooley Go Lab will have a limited rollout to start. It will be available first to startups in Y Combinator's summer cohort.

Much has changed for startups since Legora's turn in the famed startup accelerator. Teams can write code and release technology faster with coding agents. They are signing customers and growing revenue earlier, and the hottest companies seem to be raising funding nonstop. But moving faster also means legal work that once came later in a startup's life is being pulled closer to the beginning.

At Y Combinator, partner Gustaf Alströmer is seeing that shift play out in real time. In the last batch, a record 14 startups reached $1 million in annual recurring revenue — the amount of revenue a company expects to collect over a year. Alströmer said giving founders access to tools like Cooley Go Lab could help them keep that pace without creating contract-slop.

The portal includes features that review documents like nondisclosure and contractor agreements and flag issues for founders to consider. The tool also draws on Cooley Go, the firm's central hub of standard startup forms, templates, and guidance.

If you can't beat 'em, join 'em

Law firms like Cooley are facing a new reality. The better the frontier models get at legal work, the more founders and in-house lawyers may decide they can handle situations themselves rather than send them to outside counsel. Anthropic is trying to make that easier with new tools built for contract review and drafting.

Law firms are now figuring out how to stay relevant as more legal work becomes software-enabled. Some are building their own tech. Kirkland & Ellis has tapped Palantir to help it build tools to manage parts of the firm's private funds practice, while Freshfields is working with Anthropic on software that could eventually be sold to other law firms. Harvey, a leader in legal technology, says it's getting into training custom models for law firms.

Taken together, the moves point to a new attitude spreading across Big Law: If clients are going to use artificial intelligence anyway, law firms want to shape how they use it.

Bartus doesn't seem especially concerned about losing business to in-house legal departments. Cooley has been on a hot streak. Profits rose 6.7% to $922 million last fiscal year. The firm also scored a fair use win for Meta in a copyright case involving its model Llama last year, and it advised Jony Ive's hardware startup Io in a $6.5 billion sale to OpenAI.

Bartus is confident that companies will continue to depend on law firms for the important work. Cooley Go Lab, he said, is meant to help founders handle routine legal work more cleanly, not replace lawyers.

Cooley says the tool is not protected by attorney-client privilege, so founders will need to be careful about what they upload because those materials could be turned over in litigation.

"If you want actual legal advice," he said, "you need to talk to a lawyer."

• Billions of dollars are riding on the promise that artificial intelligence can absorb legal work.
• Crosby, a tech-driven law firm, built a benchmark to measure how well models negotiate contracts.
• Redline Bench is meant to help lawyers answer whether they can trust the technology's work.

Legal technology wants its vibe-coding moment. But first, it has to prove the tools can think like a lawyer.

Taking up the task is Crosby, a startup-meets-law-firm that sells basic legal services to companies, including Cursor and Rogo. On Wednesday, it released the Redline Bench, a tool built to measure how well artificial intelligence models perform real-world legal tasks, starting with contract review.

Software engineers have spent the past few years watching these systems get shockingly good at writing code and debugging errors. Now legal tech companies are chasing a similar prize: artificial intelligence that can review contracts, spot risks, and haggle terms faster and cheaper than lawyers.

But law has a problem that coding does not, says Ryan Daniels, a former in-house lawyer turned Crosby founder. "It's really hard to define 'good' or 'bad,'" he said.

Models can write code that either runs or breaks. Legal work is a murkier target. A sales contract can be edited, or "redlined," in lots of defensible ways, Daniels explains. A change that one lawyer sees as prudent, another might call too aggressive.

That ambiguity has become a headache for companies racing to automate legal work, from the scrappy neofirms to the model labs themselves. Anthropic has spent the past few months courting in-house lawyers with tools built for them. That push has been closely watched by investors. Earlier this year, Anthropic's new legal plugin stirred a sell-off in legal tech stocks.

Benchmarks are one of the main ways companies track progress. The labs building frontier models use them as stress tests, measuring whether a new system is better at tasks than the last one.

Coding has hundreds of benchmarks for evaluating models. But the legal industry still lacks a shared way to answer the question: Is the AI's work any good?

Crosby has been working on a new yardstick. The company pulled its engineers and lawyers into a tactical unit called Crosby Intelligence to build agents for Crosby's law firm and a benchmark to grade them against. That team includes engineer Sharan Ramjee, who worked on transformer models to sniff out fraud at Stripe, and Ross Weiser, a lawyer who joined from elite law firm Sullivan & Cromwell.

Crosby also partnered with Micro1, a company that helps model-makers recruit expert workers, to find more lawyers who could help define what counts as good legal work.

To build the benchmark, senior lawyers simulated software deals and marked the contract changes they considered most important at each stage of the negotiation. Those changes were turned into weighted criteria.

When Crosby runs a new test, it gives models the same contracts and asks them to make their own edits. Then a panel of three judges compares these redlines with the lawyer-built rubric. The judges vote pass or fail on each item, and the final score shows how often the models made the kinds of edits that lawyers considered important.

Redline Bench will be made public so any lab can put its models through Crosby's paces. Crosby also plans to regularly release reports tracking how major models compare.

The first release of the Redline Bench put ChatGPT 5.5 at the top of the heap, with a score of 50.5%, meaning the model's redlines matched half of the edits that lawyers prioritized. Gemini 3.5 Flash followed at 45.1%, and Claude Opus 4.8 scored 44.4%.

Crosby was able to test Anthropic's highly capable new model, Fable 5, only once before Anthropic pulled it off the shelves. The results were promising, with a score of 47.3%. When access is restored, Crosby will run the benchmark again and update it.

Crosby isn't the only company trying to measure how the models stack up. Harvey, one of the best-funded legal startups, has released benchmarks for case law research and contract review.

Anthropic and OpenAI also build their own benchmarks to measure performance on real-world tasks. But Daniels said those results can be hard to trust. Over time, the labs eventually tune their systems to perform well on their own tests, he said.

The stakes are bigger than a scoreboard. Billions of investment dollars are riding on the promise that artificial intelligence can lower legal bills and absorb work that used to pile up on the general counsel's desk.

Lawyers will only use the tools if they trust them. Crosby wants to give them a reason to.

• A personal injury lawyer apologized for filing court documents with fabricated quotations.
• The lawyer told the judge that he had begun using software from a venture-backed startup called Eve.
• The episode highlights a growing risk for the startups selling artificial intelligence to lawyers.

Lawyers keep getting burned by artificial intelligence that invents cases and makes up quotes. Now, some attorneys are naming the software they used.

Last month, a Louisiana personal injury lawyer apologized after submitting briefs that cited a real court decision but quoted passages that didn't exist. The mistakes appeared in two filings in the 19th Judicial District Court in Baton Rouge and were flagged by opposing counsel.

"I'm trying to understand how I made this mistake," Ross LeBlanc, a partner at Dudley DeBosier, wrote in a private letter to Judge William Jorden on March 27. Earlier this year, he said, he began using an artificial intelligence program called Eve to draft pleadings. At first, he checked the citations often. "They were always correct when I checked them," he wrote.

That consistency gave him confidence, and eventually, he stopped checking, he said.

"I never thought this could happen to me," LeBlanc wrote, adding that he could not be sure whether the mistake involved Eve's software or if he copied and pasted something too hastily.

Jay Madheswaranm, Eve's chief executive, told Business Insider on Thursday that after a close audit of the case with Dudley DeBosier, the company confirmed Eve "did not hallucinate any case citations in this matter," including any fabricated quotations.

Courts have slapped sanctions on attorneys for filing briefs with errors created by artificial intelligence — often called "hallucinations." Last week, Sullivan & Cromwell, one of the country's oldest and most elite law firms, apologized to a federal judge over a similar slip-up.

What's new here is the blame game. When an attorney names the tools involved, the companies behind the software are put in the spotlight and could face reputational repercussions.

Legal software companies like Harvey, Legora, and Eve have raised billions of dollars on the promise that they can make lawyers faster — and offer firms a level of reliability that general-purpose tools can't match. If their software starts to embarrass customers in court, that trust erodes.

Damien Charlotin, a French researcher who tracks hallucinations in court filings, estimates that fewer than 10% of cases identify the software used. Many lawyers, he suspects, keep that part private because they're relying on free chatbots like ChatGPT or other off-the-shelf tools that may not be authorized for client work.

Last year, a Latham & Watkins lawyer defending Anthropic in a copyright lawsuit made headlines after citing an article that does not exist. The lawyer said the mistake stemmed from using Anthropic's own chatbot, Claude, which fabricated an article title and authors.

Eve builds software for plaintiff-side lawyers using large language models, helping them draft documents, map out medical histories, and send and respond to discovery requests. The company was valued at $1 billion after it raised a $103 million funding round about a year ago. Madheswaranm said Eve now processes more than 200,000 documents and other results a month — up around 100-fold from a year ago.

LeBlanc told the judge that he had been wary of the technology generally because of the "horror stories" about hallucinated case law. He said he was persuaded after Eve pitched the tool to his firm and assured attorneys it had safeguards to reduce errors. He believed the risk was limited as long as he conducted his own legal research and directed the software to rely only on approved sources.

Then, opposing counsel in the personal injury case pointed out his mistakes.

LeBlanc's apology surfaced this month in a separate case involving a trip-and-fall at a Lowe's store. The opposing counsel found hallucinations in a brief filed by Dudley DeBosier and included LeBlanc's letter in a request urging the court to expand its inquiry into possible sanctions.

Dudley DeBosier has filed a motion to strike opposing counsel's request because it says the cases are unrelated. The firm also indicated that a lawyer used Claude to help draft the brief in the Lowe's case.

It's a view widely shared across software companies and law firms that artificial intelligence can assist in research and drafting, but responsibility for the final product remains with the human who signs the filing.

Madheswaran said Eve makes that explicit in its contracts and onboarding with new customers. The software also includes features designed to catch errors before they reach a courtroom, though they don't always work. Some errors are harder to spot than others, he said. Confirming a case exists is easier than verifying a quote is exact.

As the legal profession races to adopt artificial intelligence, mistakes are more likely to be caught. Courts are getting wiser to the technology, and opposing counsel are adjusting their tactics. Instead of only attacking legal arguments, lawyers are scanning filings for errors that could undermine the other side's credibility.

Chad Dudley, a founding partner of Dudley DeBosier, a firm with about 40 attorneys, said it trains its lawyers to carefully review generated results and requires them to agree to use the technology responsibly.

For his part, LeBlanc said he hopes other lawyers learn from his mistake. He told Business Insider on Thursday that Eve helped him move faster under time pressure, but after the errors surfaced, he felt "sick to my stomach" and couldn't sleep.

"I'm responsible for checking everything, no matter what technology comes along," he said.

He doesn't blame Eve for the blunder. Still, he's setting the tool down for now.

"I feel like, given what happened," he said, "it's fair to have a cooling off period, you know, touch grass."

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• At law firms, the billable hour is the standard way to charge clients. But timekeeping is a pain.
• The startup PointOne says it's using AI to help lawyers auto-complete timesheets and bill more time.
• PointOne raised $16 million in a funding round led by the venture capital firm 8VC.

Tracking hours is part of how lawyers get paid. It's also the bane of the profession.

A startup called PointOne wants to eliminate the most tedious part of a lawyer's job. It says its AI-powered platform passively tracks a lawyer's computer activity and uses it to complete timesheets.

The company grew revenue tenfold since July, says PointOne cofounder Katon Luaces, after signing up dozens of law firm customers, ranging from a global 1,200-lawyer outfit to solo practitioners.

Investors are taking notice. After making a small earlier investment, the Joe Londsale-founded venture firm 8VC is leading a $16 million Series A round for PointOne, Luaces tells Business Insider. Existing investors Bessemer Venture Partners, General Catalyst, and Y Combinator also participated.

Founders are flooding into legal tech, betting they can turn large language models into products law firms will trust — and competing for attention in an estimated $1 trillion industry.

Jack Moshkovich, an 8VC partner, said the market is crowded with companies trying to help lawyers do work faster. That leaves more whitespace, he said, on the operational side of the business.

Luaces isn't a lawyer. In 2019, he was a computer science major and a Google intern as the company's researchers were laying the groundwork for modern large language models.

He saw legal work as a natural target for the technology because so much of it is repetitive and text-heavy. By 2023, he and his roommate, Jeremy Ben-Meir, along with a third cofounder, Adrian Parlow, started sketching out an idea for a legal startup. (Parlow left PointOne last year and joined legal-tech giant Legora.)

When Luaces asked lawyers which part of the job they hated most, he kept hearing the same answer: timekeeping. At most law firms, the billable hour is the standard way to charge clients. Lawyers log the work they do for each client — often in six-minute increments — then tally those hours and bill accordingly. Many still track their hours in a spreadsheet or by hand on a legal pad.

PointOne's platform runs in the background as lawyers move between apps, then fills in time entries with the client, matter, a description of the work, and standardized legal codes.

Security and confidentiality are essential for law firms. Clients trust them with trade secrets and other closely held information, leaving little room for error from any software vendor.

When asked how lawyers feel about software watching them work, Luaces said their dislike of timekeeping helps overcome any discomfort. PointOne says it encrypts stored sensitive data, does not train models on firm data, and gives firms the option to use models in a private Azure environment.

For lawyers, "this is like magic beans," Luaces said.

Time savings aren't the point

Law firms are still working out how to use artificial intelligence to work faster without hurting their economics. Software that saves time can also reduce the number of hours a firm can bill.

PointOne, however, is not pitching itself as a way to save lawyers' time. Instead, it says it can help firms capture time that would otherwise go unbilled.

Some share of legal work never makes it into timesheets. Junior lawyers may undercount how long a task took, either because they're still learning or because they're embarrassed. More often, Luaces said, lawyers skip billing for small tasks because logging them takes almost as long as the work itself.

A lawyer might spend four minutes writing a client email. "I can either spend the next four minutes creating the time entry for it, or I can do more work," Luaces said. "Nine out of 10 times, everyone chooses to do more work."

He says the company's software can increase revenue by capturing billable time that would otherwise be lost.

PointOne isn't the only company making such promises. Its biggest competitor, Laurel, provides professional services firms with analytics about their operations, including time. It's raised over $150 million in funding since 2016, compared to PointOne's $20 million total.

PointOne wants to position itself for a broader shift in how legal work gets priced. Corporate clients are pushing back on soaring legal bills, and as artificial intelligence threatens to trim billable hours, firms are under pressure to test alternatives to hourly billing, including fixed fees for certain matters. Luaces said PointOne's data can help firms better understand the labor behind a matter, which in turn can help them price that work more precisely.

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• Miro's CEO says the company is plowing cash into AI subscriptions to help employees level up.
• "Our L&D budget is unlimited tooling," Andrey Khusid said.
• AI adoption is accelerating, and with it come questions about the technology's ROI.

Plenty of companies are still debating whether costly AI subscriptions are worth it. Miro has gone the other way.

Andrey Khusid, cofounder of Miro, the maker of a popular online whiteboard platform, says the company gives employees essentially unlimited access to the latest AI tools as a way to speed up how quickly they learn and work.

That approach is possible, he said, because Miro has been profitable since 2016. The company has raised $476 million to date, and Khusid suggested it does not expect to need more capital.

Khusid framed the spending as a core part of more traditional workplace training. "Our L&D budget is unlimited tooling," he said.

Rather than asking employees to learn on their own time or pay out of pocket, he said, Miro wants that experimentation to happen inside the company, as a shared effort. He later added that there should still be a clear business case for buying any tool.

Miro's strategy is part of a wider shift in tech, where AI adoption is moving from optional to expected. A new study from engineering intelligence platform Jellyfish, based on data from more than 700 companies, found that 64% now produce a majority of their code with AI assistance. Tech giants like Google are pushing employees to use AI tools more aggressively, and Microsoft has begun tying AI usage to performance evaluations. As a result, AI fluency is quickly becoming a core workplace skill rather than a nice-to-have.

Still, Khusid says many executives ask the wrong question about AI ROI. Rather than judging the tools on individual productivity gains or subscription costs, he said Miro is trying to focus on whether the company is moving faster overall.

The company tracks projects through what he described as a "discover, define, deliver" process and measures how long it takes to move from one stage to the next. The goal is to compress that timeline as much as possible.

"The most important metric from my perspective is velocity of innovation," Khusid said. "If you don't innovate fast enough, you're out of the game."

Khusid said he doesn't think the way companies use AI today is necessarily the end state. He said it will take at least until the end of this year, or even next year, to see what a workplace shaped by these tools really looks like. At that point, Miro will take a harder look at which tools are worth the price tag.

For now, he said, Miro is already seeing time savings across engineering, product, and design. That's not always the case, though. Better tools speed code generation, he said, but code reviews can still bog down projects.

"Humans have to read it," Khusid said. At least for now.

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