{"id":1431,"date":"2026-06-17T12:34:33","date_gmt":"2026-06-17T12:34:33","guid":{"rendered":"https:\/\/americanhomejournals.com\/?p=1431"},"modified":"2026-06-17T12:34:33","modified_gmt":"2026-06-17T12:34:33","slug":"one-of-legals-hottest-startups-is-helping-lawyers-finally-answer-is-the-ais-work-any-good","status":"publish","type":"post","link":"https:\/\/americanhomejournals.com\/?p=1431","title":{"rendered":"One of legal’s hottest startups is helping lawyers finally answer: Is the AI’s work any good?"},"content":{"rendered":"
\n

Legal technology wants its vibe-coding moment. But first, it has to prove the tools can think like a lawyer.<\/p>\n

Read more The next office power struggle: AI tokens<\/a><\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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?<\/p>\n

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.<\/p>\n

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.<\/p>\n

Read more Allbirds is now Smartbirds, and its AI-focused CEO says people won\u2019t even remember the shoes\u2019<\/a><\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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%.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

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.<\/p>\n

Lawyers will only use the tools if they trust them. Crosby wants to give them a reason to.<\/p>\n

Read more Bose is becoming a media company<\/a><\/p>\n<\/section>\n","protected":false},"excerpt":{"rendered":"

Legal AI startups say their tools can absorb routine work. Crosby is releasing a benchmark to test whether lawyers should trust them.<\/p>\n","protected":false},"author":1,"featured_media":1430,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[4],"tags":[],"class_list":["post-1431","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-tech"],"yoast_head":"\nOne of legal's hottest startups is helping lawyers finally answer: Is the AI's work any good? - American home journals<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/americanhomejournals.com\/?p=1431\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"One of legal's hottest startups is helping lawyers finally answer: Is the AI's work any good? - American home journals\" \/>\n<meta property=\"og:description\" content=\"Legal AI startups say their tools can absorb routine work. 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