It's not every day that a white-shoe-lawyer-trained-at-Stanford-turned-startup-general-counsel decides to upend the entire legal profession. But that's exactly what Ryan Daniels has done alongside his cofounder, John Sarihan. You could say the groundwork was laid in childhood: the son of two law professors and raised with a curiosity to question the status quo, Ryan had adventurous tendencies and always knew he wanted to work in the legal field.

For a while, Ryan was a familiar sight in our New York office as the newest entrepreneur in residence. When we wanted to hear more about how his startup idea was developing, he popped up on Zoom. “I’m in India,” Ryan explained casually, as though he’d only popped down to the corner store, “meeting with legal process outsourcing workers to understand how they do their jobs.” What began as a mysterious disappearance turned out to be field research, the kind that would shape the foundation of Crosby Legal: an AI-first law firm built around contract automation.

Scales were tipped from the beginning

Ryan’s path took him through undergrad at Penn, then joined early-stage startups like HiredScore (later acquired by Workday) and A.Team (which raised $60M from Insight, Box Group and NFX) as a founding team member and general counsel. In between, he went to law school at Stanford, then cut his teeth in big law at Cooley. Those experiences gave him a powerful skillset of legal fluency, startup grit and product sensibility.

John, for his part, also graduated from Penn (in the prestigious M&T program) and accelerated quickly during his four years at Ramp, rising from engineer to tech lead, where he saw a best-in-class company automate complex, repetitive workflows. While there, he managed money licenses and saw firsthand how fast-growing companies were grossly underserved by existing legal and regulatory support services.

At Crosby, their experiences have converged into a thesis: the bulk of legal work lives in a “dead zone.” This is the territory between the $1,000-an-hour white-shoe law firms and the fully manual contract review of overstretched operators. Every startup knows the pain—NDAs, MSAs, DPAs, vendor contracts, customer agreements—documents too important to ignore, but not critical enough to warrant heavyweight legal bills. With John, Ryan tested his hypothesis in those early trips to India, and the two came to believe that this middle zone is both automatable and underserved.

The missing middle of law

There’s a massive demand for a faster, less expensive legal service–to the tune of $18B and growing– with enterprises offloading high-volume, low-complexity work. But startups and mid-market companies rarely get that treatment; they either pay up for big law, cut corners with ChatGPT, or worse, skip review altogether. Crosby believes these companies need a new legal solution—one built AI-first, designed to handle routine contracts at the speed and cost growing companies demand.

Part of Crosby’s differentiation lies in its business model. Instead of the traditional pay-by-the-hour billing model that leaves incentives misaligned and founders guessing at final costs, Crosby uses a predictable, volume-based approach and charges based on how many contracts get reviewed. Clients know exactly what they’re paying for, which turns legal from a variable expense into a reliable operating function. This flips the old economic model on its head and creates efficiency for both finance and legal teams while aligning incentives between the service provider and customer to deliver a better, faster product.

Crosby’s model blends technology with tailored playbooks. Today, clients submit contracts by email and receive redlined versions within hours, complete with commentary tables and drafted email responses for negotiation. Law firms can be highly profitable but they are not designed to scale efficiently. Crosby is changing that by applying software economics to routine contracts. Over time, the company’s goal is to own the contracting workflow from intake to execution, addressing the growing demand for faster, less expensive legal services.

A complementary duo

While Ryan anchors Crosby with legal and operational experience, his co-founder John delivers a technical prowess. John is focused on embedding AI deeply into the contracting process, transforming repetitive legal tasks into intelligent, structured workflows that get smarter with every use.

Together, they bridge the gap between engineers and lawyers to come up with creative solutions and make the best possible product and company decisions. A prime example: early in their startup journey, John challenged Ryan to an AI-vs-human duel. “I’ll bet I can replace you with AI in a month.” So Ryan set out reviewing contracts manually while John mirrored Ryan’s actions and built an impressive data pipeline overnight. Ultimately, the AI that John built could accomplish many aspects of review faster than Ryan, yet it missed nuanced edits that Ryan made. This solidified their conviction that AI with a human in the loop is a perfect union. The pairing enabled them to cut initial review times from 24 hours to 12 in short order.

Just as Ryan was quick to fly around the world for market research, John is quick to turn a mundane assignment into a quest that should be conquered. When Ryan was unable to attend a multi-day conference for Fortune 200 general counsels, John stepped into the role literally. He swapped his hoodie for a crisp suit and each day, he was the first to arrive and the last to leave. By the end, he held the business cards of all 200 GCs.

Together, Ryan and John are proving to be a force of nature, leaning into their natural tendencies of questioning the status quo and rolling up their sleeves to accomplish whatever task is required. Since launching earlier this year, that combination has already delivered results, with Crosby reviewing thousands of customer contracts for fast-growing companies like Cursor, Clay and UnifyGTM.

The Next Chapter of Legal Work

Until recently, contract automation was brittle: rules-based redlining couldn’t capture nuance, and CLM tools largely organized rather than executed work. With today’s models, Crosby can automate judgment-heavy but pattern-rich tasks while still keeping humans in the loop for final calls. The result is a system that combines the speed and fair billing of software with the quality and care of services.

One of the most striking signals from customers is the enthusiasm from sales teams. Contract delays often stall deals and create friction in the sales process. Crosby ensures that salespeople aren’t blocked, giving them the confidence to move deals forward without waiting on legal bottlenecks.

As companies race to sign enterprise customers, the volume of contracts explodes. Ten MSAs per month can quickly become 50, and a founder reviewing them on nights and weekends is a recipe for missed revenue. Crosby helps these teams close deals faster without burning cash on expensive law firms.

There is also a powerful network effect emerging in this business. Contract clauses function like code, and Crosby is building a living dataset of them in real time. Each time customers negotiate with new entities, Crosby captures and maps terms across contracts. That creates data moats and technology leverage, so the next thousand contracts are faster and easier than the first thousand. It is a compounding advantage driven by both scale and improvements in reasoning models.

Crosby has already won customers like Cartesia, Alloy and Overjet, where the pain is sharpest for high-growth startups without a general counsel. Soon, Crosby will expand into other verticals, servicing the specific needs of specialized industries.

The ripple effects will extend across the business. Predictable billing gives finance teams tighter control over spend, while faster reviews help sales leaders accelerate deals and reduce friction with enterprise buyers. We believe the same levers of efficiency that make Crosby indispensable to startups today will compound with time as larger organizations adopt the platform, turning legal from a bottleneck into a driver of growth.

By then, the company envisions offering not just a service, but an indispensable AI-driven platform for contracts that speeds negotiation, ensures compliance and captures the data exhaust to make every deal smarter than the last. It’s the blend of Ryan and John’s founder qualities with the early traction they’ve achieved that gave us conviction that Crosby is reshaping legal work, and why we were excited to lead their Series A.

For Ryan, the path from Cooley to Crosby is more than career evolution; it is a return to his roots with a modern twist. “I am building the product I wish I had,” he says. For founders drowning in paperwork and GCs stretched too thin, it is the kind of product that could redefine what legal work looks like.