Crosby raises $60M Series B and crosses $1B in client contracts using AI agents to run a law firm end-to-end

It back test extremely well.

What a crazy timeline we are in. Well, thank you so much for coming on and breaking it down for us. Let's let's be sure to hang out.

Let's hang soon.

All right, you guys. Cheers.

See you.

Let me tell you about Sentry. Century shows developers what's broken and helps them fix it fast. That's why 150,000 organizations use it to keep their apps working. And without further ado, we have Ryan from Crosby. How you doing, Ryan?

Welcome back.

Hey guys, good to see you again.

Dude, you're on you're on here like every week.

It's getting ridiculous.

Yeah, it's getting a bit much. Let me guess. Another one. You should just bundle all the fundraisers together into like uh series alphabet. Then we just do

I never get to see you guys in the

It is. It is more strategic to break them up. But tell us what happened. How much did you raise? What's going on?

We have two announcements. The first announcement is we've raised $60 million led by Lux series B.

And our second announcement,

thank you. The second announcement is we did some math last month and we have now closed contracts worth over a billion dollars for our clients.

It's a big milestone for us.

Okay. Million dollar for the client. That's good.

Was there a power in there? Was there like one sneaky $950 million?

Did you get 1% of this new Open AI round in there? Somebody was like, "I'm going to review one clause." And you're like, "I'm going to No, it sounds like it sounds like there's a lot of lawyers using it."

That's right. I mean, these are small deals, so it's a lot of velocity. I think definitely my corporate law friends are like, "That's like one deal for me, so that's not interesting, but for us, that's a big number." That makes sense. So, it's a really good milestone.

Yeah. So, yeah. Yeah. T take us through I mean, it sounds uh like like the the shape of the work that is being augmented by Crosby these days.

Yeah. So, you know, we're about a year and a half into it. We announced our seed um around 230 days ago. We do commercial agreements. These are the sale of agreements, MSAs, NDAs, um BPAs for like fast growing AI companies. Now we're branching out, but since the beginning, we've been a law firm. So we have about 30 lawyers here who I'll give a shout out to are just the last day of the quarter. They're working so hard for our clients getting the deals closed and we close deals fast, like in a couple hours. And so this idea has just taken off with a lot of tech companies now and and now even bigger clients who just want to close faster.

Uh how how have you been processing you're kind of uh I would say very tapped into how well the models work in different roles. I'm curious your view on

uh how application layer legal AI companies will do uh compared to just the labs themselves, right? I feel like every other day on X somebody says wait

this LLM

seems to be doing just as much as you know this application layer company you guys are using all the models internally for your own internal tools but like how how are you processing kind of what feels like well ultimate in the same way we saw with codegen where you have application layer companies and foundation model companies and then you have foundation models with their own applications I'm assuming we'll see that in legal but uh how have you been kind of processing it?

So I mean that's that is the question we have to ask ourselves every day. We think that uh code generation more or less is kind of like a year and a half ahead of the sort of non-selfverifiable domains. So anything that's not like math or code and law is one of those but it's a huge service area and our sort of like insight a couple years ago was let's you know not think about these sort of like AI co-pilots that are kind of like you know the equivalent of what cursor was a year and a half ago when you kind of hit tab to autocomplete but these long form agents with bigger context that could do a full job end to end. And if you have agents that can do entire swads of legal work, then the best thing you should do is start a law firm because you're selling work to clients, not, you know, fractions of work or kind of helping them along. And in truth, we were ahead of the models. And so we were selling something that like we weren't able to fully automate. And as the models are progressing, we're seeing more and more of a compounding advantage as, you know, we have more and more contracts that we're processing. We have more and more lawyers that were able to help us, you know, tune judges and and, you know, like create better agents. And so we're able to just do endto-end work in a way that like if you're just selling a legal, you know, co-pilot, I think you're going to face a lot of competition just from the models with no customization.

Yeah.

Sorry.

Wild John's back. Uh yeah, wild wild moment. Um what I'm assuming you'll also face competition from clients that are just like hey we can should should we should we have an in like uh should we have an in-house uh lawyer that we can you know speed up uh but but everybody's competing with everyone but uh yeah

how are you how are you tracking the legal education market uh I've seen it I it it seems very hard to predict for me like there was this weird spike I want to say like it was maybe post chatbt where there were like more people signing up for a law school and that was like sort of contrarian based on the model capabilities like the AISF discourse but maybe it makes more sense like are you tracking that data and then are you tracking like how legal education is changing uh I imagine that uh using AI tools already happening in middle school for a lot of people high school definitely college definitely law school uh how will that how will that all trace through and how closely are you following I mean, I think every industry is asking themselves like how do people get the entry- level jobs to learn those skills so they become really good and senior and get leveraged by agents. Um, I I went to law school at Stanford. I'm talking to a lot of professors there who are struggling with this question. I think our insight for now, like the stat we found recently is that the top 100 law firms last year made a little under $70 billion in just profit just in 2025. That's just paid out to their partners. That's just salary. and bigger than

says there's not enough

good year

that's so good

and that was that was more money than Google spent on all their R&D and so like our insight was

which is great so like if we could just put some fraction of the profits law firms are making into building better tools and experiences for lawyers and for their clients I actually think the legal industry gets a lot bigger and so it's like for a a person in law school today

it's a good time to be thinking like how can I just build better stuff and that's just a new way of lawyers is thinking.

Okay, that's one way to put the profits to work. Uh, let me pitch you another way. If I'm a partner at a law firm

and I see that yes, agents can do the work of the the associates that I would be hiring. Yeah. Uh maybe I you know uh contrarian in me wants to still hire associates just for the mentorship and uh and building like the pipeline of partners that will do more human work, more deals work, more interpersonal relationship work, but I know that if I don't start buying and paying for that service right now, even if I'm getting less margin on it loosely because I'm paying an associate a bunch of money and it's work that an AI agent like sort of could do and Maybe they're a little bit more free. I I I'm actually incentivized to figure out how to accelerate them faster in their career. Have them start working on larger, stickier deals that AI can't necessarily navigate just yet.

Yeah. I mean, I I I buy the argument. Like, I think that there's two jobs for lawyers really to focus on right now. One is just doing client-f facing work and being really good at

being like, you know, be talking to people and understanding what their points of view are and not being buried in the sort of paperwork like a typical associate. And the other is being able to explain reasonably well to an engineer or a researcher what it is you're doing and what you're thinking about and all the subtleties of context.

Yeah.

And those two things I think are both things that if you're not hiring enough lawyers, you can't do well and you can't build better legal technology and experiences. And so I think we're feeling this and every law firm is feeling like you just need people to be really thoughtful about doing both those jobs.

Yeah. Yeah. Are you guys fine-tuning any models, you know, based on fine-tuning like open source models, or is that not even, you know, I've seen like Finn and and Notion have had some success with this.

Is that even a good use of time right now? Because I'm assuming your guys' like actual like inference costs are not that high relative to what you can charge clients even if you're using the frontier models. But

how are you thinking about that? I think again if we just look at code generation as like the blueprint for the future you'll see like a lot of the codegen companies got a lot of lift from just like you know the main you know three big models

and over time you have to start fine-tuning your models as you get scale as you get data and as you need a more competitive edge so we're not there yet we have a lot of lift from just getting the right context to models building the right agent flows like um just doing some reinforcement learning on like basically you know we work with really you know open athropic and Google's models but yeah in a year and a as you get really specialized in use cases of law. I I I'm sure like we're going that direction and part of the reason for this funding and doing it so quickly is to start investing in a research team that can can kind of push the boundaries