Crosby

As of 2022, an estimated 137K new startups emerged every day. Since then, the rise of generative AI has further reduced the cost and complexity of starting a company. When these companies sell their product to other companies, they use contracts, and those contracts usually pass through a lawyer. Legal review has become a common chokepoint in the B2B sales process, where a request for a signature can turn into weeks of negotiation. Poor contract management erodes an estimated 9% of annual revenue, and as of 2025, legal was involved in about 75% of contracts in the business services sector.

A big part of the problem is the longstanding billable-hour model used by the legal industry, which rewards time spent rather than quick turnarounds. A basic contract review from a law firm can cost from $450 to $3K, and more when it includes proposed edits. The alternatives include using generic AI models (which are known to make mistakes) or hiring in-house counsel (which costs an average of more than $140K per year in California as of October 2026). AI-enabled associates can draft NDAs up to 70% faster than their peers, and technology spending by law firms grew 9.7% in 2025, the fastest real growth on record. The largest legal AI companies sell that technology to lawyers who still bill by the hour. Harvey and Legora sell to law firms, at valuations of $15.5 billion as of September 2026 and $5.6 billion as of April 2026, while GC AI sells to in-house legal teams at a $555 million valuation as of November 2025.

Crosby, founded in 2024, is a law firm that reviews and negotiates commercial contracts for startups, and it calls itself “the agentic law firm built for execution”. Unlike other legal AI companies, Crosby is a registered law firm with malpractice insurance and liability for each contract it reviews. It is agentic because AI agents do the first pass on every document, with human lawyers reviewing the work and making the tougher judgment calls. It also aligns with clients by charging a fixed fee per contract instead of billing by the hour, so it earns more by finishing contracts faster. Crosby aims to take on contract work startups would otherwise send to outside counsel, rather than sell law firms better tools as other legal AI companies do.

Crosby was founded in September 2024 by Ryan Daniels (CEO) and John Sarihan (CTO). The son of two law professors, Daniels has worked in law and startups for over a decade. He started his career in 2014 as chief of staff at HiredScore, an HR software startup, before going to Stanford for law school. He then spent a year as an associate at Cooley LLP, one of the largest firms serving the tech industry as of 2025. After that, he handled Fortune 500 contracts as general counsel and a founding team member at the startup A.Team.

After leaving A.Team, Daniels spent five months as an entrepreneur-in-residence at Bain Capital Ventures. There, an investor connected him with Sarihan, who spent four years at Ramp* as a tech lead and engineering manager, and they began brainstorming AI applications for law. Sequoia already knew Sarihan from Ramp, and later led Crosby’s seed round.

A few months before starting Crosby, Daniels visited legal process outsourcing firms in India, which compete in a $22.2 billion global market as of 2025. After seeing the demand for faster and cheaper legal services, Daniels co-founded Crosby with Sarihan. In the early stages, Daniels handled the legal review himself, while Sarihan automated as much of the process as possible. Crosby quietly began operations in January 2025, and publicly launched in June 2025. Daniels has described Crosby as a “neofirm”.

Crosby is a law firm that reviews, redlines, and negotiates commercial contracts on behalf of its clients, with AI agents doing the first pass and licensed attorneys reviewing all of the work. Crosby does not sell software to other law firms, and clients don’t have to learn a new tool in order to benefit from Crosby’s services. Instead, clients send contracts in and get completed work back.

Crosby describes its service as providing expert attorneys who review all work and manage legal AI agents that research, analyze, and draft. It also offers market data from contracts negotiated against 76% of the Fortune 100, and a custom memory of each client’s preferences.

Source: Crosby

Law firms’ time is expensive and only partly billable. Expensive firms can charge $1K per hour, yet the average lawyer bills just 2.9 hours a day, with the rest going to administrative tasks, training, and firm meetings. Ross Weiser, Crosby’s Director of Legal, found the ChatGPT deployment at his former firm, Sullivan & Cromwell, unhelpful for complex tasks and frustrating to work with, which is the gap a law firm built around its own agents is meant to close.

Customers send contracts to Crosby through Slack or email at any time of day. These requests are automatically uploaded to a central system called Bailiff that also stores relevant documents like agreement templates, policies, guidelines, and rules. Bailiff determines each request’s priority and estimated turnaround time, then routes it to the right lawyer in seconds.

Crosby uses a suite of eight AI agents to conduct the first pass on every document. These agents are built on models from OpenAI, Anthropic, and Google, and trained on thousands of contract reviews and 50K clauses hand-labeled by the company’s in-house lawyers. Each agent handles a different part of the negotiation process, whether that’s pulling relevant context from past contracts, proposing changes to specific words or phrases, or generating comments explaining the revisions.

The agents annotate the contract, flag common issues, prepare preliminary redlines, generate a confidence score, and send the annotated document to a Crosby attorney. As of October 2026, Crosby had more than 50 licensed attorneys, up from 30 in March 2026. The attorneys act as quality assurers, reviewing the agents’ markups and addressing the legal nuances the agents missed.

The final annotated document that Crosby provides tells customers which terms to accept and which ones to push back on, based on prior context about the customer’s business. Crosby reviews commercial contracts like master service agreements (MSAs), data processing agreements (DPAs), and non-disclosure agreements (NDAs). Sequoia said in June 2025 that customers including Cursor and Clay were processing sales contracts in two hours or less. Investors see it as a “sales enablement” engine for the GTM teams of fast-growing startups who want to close deals without having contracts stuck in legal.

Source: Crosby

Each client’s preferences are set as a negotiation playbook agreed with Crosby. A playbook can specify, for example, that the agent accepts a limitation-of-liability cap below a set threshold, defers to a standard position for mid-sized caps, and escalates anything uncapped to the client’s general counsel. Cursor’s senior counsel described the arrangement as Crosby reviewing and escalating to her “in accordance with our agreed playbook”. This lets the agents propose a resolution for routine disagreements before an attorney reviews it.

Crosby’s process is designed to improve with use. A feedback loop is built in, so the agents improve with every clause and contract they review. Crosby stores those preferences in a per-client database it calls Crosbrain, and builds a knowledge base for each customer that becomes more bespoke over time. Crosby’s attorneys also suggest prompt changes to the company’s AI researchers, explaining why one answer is better than another from a legal standpoint.

Source: Crosby Intelligence

Crosby has steadily added features. One unverified report says that in October 2025 it expanded intake beyond Slack to include email, set a four-hour review service level agreement, and added commentary tables and drafted negotiation emails to its reviews. In June 2026, Crosby launched Crosby Intelligence, a research organization within the company that publishes a contract-negotiation benchmark for AI models, funds a research fellowship, and hosts a speaker series. On its RedlineBench, which simulates multi-turn contract negotiations, the top model scored 50.5% as of October 2026, and every model tested tended to over-accept the counterparty’s terms, which is the gap Crosby’s attorneys review for.

Customer

Crosby typically works with startups that have no lawyers or a single in-house general counsel. These startups either use a chatbot like ChatGPT or hire an expensive law firm that charges $500 to $1K per hour. As of March 2026, Crosby charged from $250 to $1K per contract, or about $10 to $50 per page. One unverified estimate puts a typical contract at around $400. Traditional firms price basic reviews similarly, so Crosby’s difference for these customers is speed and a single bill per contract rather than a lower price.

Most of Crosby’s named clients are high-growth AI startups. Cursor, the AI coding company, had used Crosby to review 2K contracts by March 2026 and reported a 50% cut to its contract review time. Grace Kneapler, then a GTM specialist at Cursor, said in October 2025 that speed mattered because “time kills all deals”.

Source: Crosby

Clay had sent Crosby about 1K legal requests as of October 2026, with a median turnaround under two hours while its monthly contract volume grew about fivefold. Simile, an AI startup building digital simulations of people, cited Crosby’s turnaround speed as the fastest it had found while its revenue grew 28x over six months. Daniels also sells directly to founders. At a CEO retreat hosted by Index Ventures in mid-2025, he signed three AI startups, including Cartesia and Parallel.

Market Size

Market size estimates for Crosby differ. The narrow legal AI software market encapsulates the tools Crosby builds, but not the services it provides. Because adoption is still early (78% of law firms were not using AI in 2024), that market has a smaller total size and a steeper projected growth rate. The broader scope of the legal services market encompasses all of the labor that Crosby seeks to replace. Since that industry is far older and well-established, it has a larger total size and a flatter projected growth rate.

The majority of Crosby’s operations are in the United States. The US legal services market has an estimated value of $318.7 billion in 2026, and is projected to grow to $488.1 billion by 2035, a CAGR of 4.8%. The global legal services market has an estimated value of $1.1 trillion in 2026, and is projected to grow to $1.4 trillion in 2031, a 4.6% CAGR.

At a smaller scope, the global legal AI market was valued at $1.4 billion in 2024 and is projected to reach $3.9 billion by 2030, a 17.3% CAGR. The global AI contract analysis tools market was valued at $3.3 billion in 2025 and is projected to reach $12 billion in 2030, a 29.4% CAGR. Crosby’s revenue is counted in the legal services market, even though its agents do much of the routine work.

Competitive Landscape

The work Crosby takes on mostly comes from legal process outsourcing companies and small, boutique contract-focused firms, rather than from Big Law firms like Kirkland & Ellis or legal software companies. Big Law firms typically serve larger enterprise clients, while companies like Harvey, Legora, and Clio sell software to law firms. Harvey, for instance, builds legal AI tools for contract analysis, compliance, due diligence, and litigation that were used by more than 100K lawyers across 1.3K organizations as of March 2026.

Crosby’s customers, on the other hand, are mostly startups. Companies like GC AI sell software to in-house legal teams. They share part of Crosby’s customer base, but they sell software, while Crosby is a law firm that sells legal services and is liable for the result. Crosby also competes with frontier AI labs and Microsoft, which in 2026 began building contract review into Claude and Word.

A newer group of AI-native law firms has structures similar to Crosby, with software and AI agents doing most of the work and licensed attorneys reviewing it while the firm carries liability. Lawhive, Eudia, and General Legal all follow some version of this model. Lawhive serves consumers and small businesses, and Eudia serves large corporate legal departments, while General Legal sells to high-growth companies, the same customers as Crosby. These firms, along with contract-review software vendors like Ivo, most closely resemble Crosby and are profiled below.

Competitors

Lawhive: Lawhive, founded in 2019, is a British AI-native law firm that runs a network of human lawyers on its own technology platform. It operates three regulated law firms, two in the UK and one in Arizona, with about 500 lawyers, and reported more than $35 million in annual revenue as of February 2026. In February 2026, it raised a $60 million Series B led by Mitch Rales, the co-founder of Danaher, at an undisclosed valuation. As of October 2026, it had raised a total of $114.2 million from investors including Balderton Capital, TQ Ventures, Episode 1, and GV. Unlike Crosby, Lawhive serves consumers and small businesses on matters like property transactions, family law, and landlord-tenant disputes, and it launched in the US in 2025 with an office in Austin.

Eudia: Eudia, founded in 2023, sells AI software to corporate legal departments, with customers including DHL, Cargill, Intuit, and Stripe. In September 2025, it opened Eudia Counsel, an AI-augmented law firm for contracting and M&A diligence licensed under Arizona’s alternative business structure program. In February 2025, it raised a $105 million Series A led by General Catalyst, at an undisclosed valuation. As of October 2026, it had raised a total of $105 million.

Ivo: Ivo, founded in 2021, is a contract intelligence platform that automates contract review for clients like Meta, Uber, IBM, Atlassian, and Reddit, breaking each review into over 400 separate AI tasks. Its revenue grew sixfold between February 2025 and January 2026. In January 2026, it raised a $55 million Series B led by Blackbird Ventures at a reported $355 million valuation. As of October 2026, it had raised a total of $77.2 million from investors including Uncork Capital, Icehouse Ventures, Fika Ventures, and Costanoa Ventures. Ivo sells software to in-house legal teams and carries no liability for the contracts its customers sign; it planned to triple its 60-person headcount by the end of 2026.

General Legal: General Legal, founded in 2025, is an AI-powered law firm for high-growth companies. Like Crosby, its attorneys work in clients’ Slack channels to process contracts faster, but it publishes flat fees, including $500 for a standard contract review. In February 2026, it raised a seed round led by Audacious Ventures and Y Combinator, following a pre-seed led by BoxGroup and Susa Ventures, at undisclosed valuations. As of October 2026, it had raised a total of $11.5 million across both rounds.

Crosby operates on an asset-light services model. It owns its software and its accumulated contract data, and its main cost is the attorneys who review every document. As of June 2026, about 45 of its roughly 100 staff were attorneys. Its agents also run on third-party models from OpenAI, Anthropic, and Google, so model usage is a second cost that grows with volume. Because Crosby bills per contract, its revenue grows as clients send more documents rather than as they add seats. This gives Crosby an incentive to improve its product, because if its clients save more time, they can close more deals, which means more contracts processed by Crosby.

As of March 2026, Crosby returned most reviews within a few hours. With a traditional firm, a sales representative could wait days for a response. Under the billable-hour model, lawyers track their work in six-minute increments and send multiple invoices for each contract. In contrast, Crosby charges by the document, and bills clients once per contract regardless of how many rounds of review it takes.

This pricing structure aligns Crosby’s incentives with its clients’ incentive to close deals faster, unlike traditional law firms. In 2024, the top 100 American law firms recorded $69 billion in net income. Daniels has said that profits per partner is the key metric law firms measure themselves by. Crosby, on the other hand, earns more by processing as many contracts as possible, as efficiently as possible.

Source: Crosby

In its first six months of operations, Crosby reviewed over 1K MSAs, DPAs, and NDAs for companies like Cursor and Clay. In June 2025, it reported a median review time of 58 minutes, and said GTM teams reported closing deals about 80% faster. By October 2025, the number of GTM teams working with Crosby was growing 30% month over month. It returned over 90% of its documents within a few hours and was processing 1K contracts every three weeks.

By March 2026, Crosby had about 100 clients, including startups like Cursor, Clay, and Cognition, as well as real estate firm Tishman Speyer, which managed $64.4 billion in assets. It had negotiated over $1 billion in contract value, up from $30 million when it launched in June 2025. Its agents had reviewed 13K contracts, and Crosby’s revenue had grown about 400% from October 2025 to March 2026.

In October 2026, Daniels wrote that Crosby’s revenue had doubled in each of the previous three quarters. The same month, Crosby published results from controlled trials in which its lawyers’ average review time fell 74% on one client’s NDAs and 80% on another client’s MSAs after the agents were tuned.

In March 2026, Crosby raised a $60 million Series B co-led by Index Ventures and Lux Capital, with participation from Sequoia, Elad Gil, 01 Advisors, and Bain Capital Ventures. The round reportedly valued Crosby at $400 million as of March 2026. Prior to this, in October 2025, it had raised a $20 million Series A from Index, Bain Capital Ventures, and Elad Gil, with participation from Sequoia, Cooley LLP, and Patrick Collison,at an undisclosed valuation. In June 2025, it raised a $5.8 million seed round led by Sequoia, with Bain Capital Ventures and angel investors including the founders of Ramp, Instacart, and Flatiron Health, at an undisclosed valuation. As of October 2026, Crosby had raised a total of $85.8 million across three rounds in nine months.

Contract Management Features

Crosby already handles a large share of its clients’ contract volume: Cursor had sent it more than 2.1K requests as of October 2026, and Clay about 1K. That volume gives Crosby a position to manage contracts after they are signed, not only to negotiate them. Its Series B announcement listed a platform for clients to oversee and weigh in on Crosby’s work among its experiments in March 2026.

One unverified report suggests Crosby could add contract lifecycle management (CLM) features such as obligation tracking, renewal reminders, and benchmark analytics, along with vertical-specific templates like HIPAA-ready business associate agreements and multilingual EU DPAs. The same report suggests integrations with Salesforce, HubSpot, and DocuSign that pick up contracts at each stage of a deal. The market for AI contract analysis tools was projected to grow from $3.3 billion in 2025 to $12 billion in 2030, and each feature would let Crosby capture more of that spending from clients whose contracts it already reviews.

Market Expansion

Crosby has room to expand both to new customers and to new regions. Daniels has said that legal services for individuals, such as leases and child support, are “horribly underserved” by lawyers, which makes them a candidate market for the same model. One unverified estimate puts Europe at roughly 30% of global CLM spend, and the same report says EU and UK buyers favor hybrid lawyer-in-the-loop models because of GDPR enforcement and the EU AI Act. Lawhive shows that an AI-native firm can run regulated practices on both sides of the Atlantic, with two firms in the UK and one in Arizona as of February 2026.

Autonomous Negotiations

Lux Capital partner and Crosby investor Grace Isford described “multi-party autonomous negotiations” in March 2026 as a negotiation structure for the future. Under this structure, each party would have its own set of agents that know its preferences and risk tolerances. These agents would go back and forth and reach an agreement on their clients’ behalf, producing an auditable record of the negotiation that both parties can review. Crosby’s Series B announcement listed experiments with a counterparty-response simulator and voice agents that negotiate on behalf of clients. In July 2026, Crosby said it planned to buy professional liability insurance for its agents, a step toward letting them complete work without attorney review.

Regulatory Constraints

Operating as a licensed law firm means Crosby is subject to legal-practice regulation in every jurisdiction it serves. In most US states, a law firm must be owned by lawyers, which limits how a firm can raise outside capital. Crosby operates as a registered law firm with Daniels as its sole proprietor, and one unverified report describes a second entity, Crosby Legal Inc., that builds the software alongside the law firm, Crosby Legal PLLC. That structure keeps outside capital in the software company, so it depends on the rules on non-lawyer ownership and fee-sharing between the two entities staying as they are. Arizona is the main exception to those rules. It had approved 136 alternative business structures that allow non-lawyer ownership as of April 2025, up from 19 in 2022, and Eudia runs its law firm under that program.

Attorney Costs That Scale With Volume

Crosby’s model depends on licensed attorneys reviewing every document, so its largest cost grows with its volume. As of June 2026, about 45 of its roughly 100 staff were attorneys, and one unverified report says it must hire and manage licensed attorneys across each jurisdiction it serves. Crosby has said it plans to insure its agents so they can work without attorney review, but as of October 2026, attorneys still reviewed every output. Robert J. Couture, a senior research fellow at Harvard Law School’s Center on the Legal Profession, argued in March 2026 that law will remain a human-first profession because clients need confidence that a firm stands behind its work, which would keep the attorney cost a permanent part of the model.

Client demand could add to that cost. Jacqueline Wibowo, then head of business operations and finance at Cartesia, said in October 2025 that she would pay extra for Crosby to function more like an account manager across more kinds of legal work, which would mean attorney hours that per-contract pricing does not charge for. Robin AI, which paired contract software with a managed legal services team, failed to raise about $50 million, a figure from one unnamed source, and was listed for a distressed sale in October 2025; its services team was sold to Scissero that December.

Frontier Labs Building Contract Review

Crosby’s agents run on models from OpenAI, Anthropic, and Google, and the labs and Microsoft have started building contract review into products customers already use. In January 2026, Anthropic launched a legal plugin for Claude Cowork that reviews documents and flags risks. In May 2026, Microsoft released a legal agent for Word in early access through its Frontier program, which reviews contracts clause by clause against a playbook and returns redlines as tracked changes. Microsoft had hired Robin AI’s former VP of AI and several of its engineers and product specialists into the Word team in January 2026. If these tools reach general availability inside software startups already pay for, customers could get a first-pass contract review at little extra cost, which would pressure Crosby’s per-contract pricing.

Legal review has become a common chokepoint in the B2B sales process, and the billable-hour model gives law firms little reason to move faster. Crosby is a registered law firm that carries malpractice insurance and liability for each contract, with AI agents doing the first pass and attorneys reviewing all of the work. Its median review time was 58 minutes as of June 2025, against a process that historically took weeks, and it charges a fixed fee per contract.

The model has worked with fast-growing startups. By March 2026, Crosby had about 100 clients and over $1 billion in negotiated contract value, and it had raised $85.8 million across three rounds. Its main risks are that its attorney costs scale with its volume, that legal-practice rules limit how it is structured and where it can operate, and that frontier labs and Microsoft are building first-pass contract review into their own products.

*Contrary is an investor in Ramp through one or more affiliates.