Inside Legora: Jude Law Generated $50M Pipeline | Are They Undervalued at $5.5BN? | Patrick Forquer

How much did the Jude Law cost?

I can tell you it was worth every penny.

Was it?

So, last month alone, we generated over $50 million of qualified pipeline.

When I started, we were at 40 people. Today, we're over 500.

When we get into a deal, we get into a pilot, and we convert pilots 78% of the time into a closed-won opportunity. It's a death match on every deal. It's super competitive. We've got to play defense and offense at the same time, and that's what makes it fun.

This market is being made right now. This is one of the hottest markets of all time. It's more about time than money right now. When you have momentum and you have an advantage, press the advantage.

Ready to go? Patrick, dude, I've heard so many good things. I was literally just chatting to Chayton and Logan before this show. They gave me phenomenally helpful insight, especially Logan. So, thank you so much for joining me, dude.

1. The Biggest Sales Lesson Carried From Braze to Legora

Oh, thanks so much for having me. It's awesome to be here.

So, you were at Braze for 6 years.

Yeah.

What was the single biggest sales lesson that you took with you from Braze to Legora?

2. How Legora Onboards 40-50 New Hires Every Two Weeks

That's a great question. I think the biggest thing that we did really well at Braze that I've taken over is implementation change management. Braze is really hard to implement, or at least it was when I was there. You're on a legacy product, and you're consolidating 1, 2, 3, 4, 5 different tools into 1 tool. Implementations take 6 to 12 months. It's a lot of effort, there's a lot of stakeholder management and technical work streams, all these different things.

For us at Legora, obviously we have an amazing product, but at the end of the day, our focus and our obsession is around helping our users adopt those tools into their workflows, which is really hard. General change management strategies, and taking all the learnings I took from Braze and applying them to Legora, is probably the biggest thing.

So, I had Matt Fitzpatrick on the show, and this is why I don't normally send out the schedules, because they just get by the wayside very, very quickly. Matt Fitzpatrick, who's the CEO of Invisible, which is a data provider, was like, "You can't sell into enterprise without FDEs today."

Yeah.

Is that true? And when you reflect back on what works in change management, what's the biggest advice?

Yeah, so there are a couple of things that are still true, and I think some things that are different in an agentic world. The things that are still true are that you still need a tremendous amount of executive sponsorship and support.

Yep.

The joke we used to make when I worked in consulting was that the 2 things people hate the most are the way things are and change. So, you need top-down sponsorship, you need bottom-up champion building, and all the normal adoption frameworks that you would use in traditional change management.

I think the biggest thing with agentic work, and why FDEs are required, is that we have both forward-deployed engineers and forward-deployed legal engineers. These are typically big-law attorneys who understand how individual practice areas work within a law firm, as well as how corporate legal departments work within that broader context.

Within an agentic tool like Legora, you log in and you see the agent. It's like the proverbial blank page, right? There's no sequential set of things that you click, like in SaaS. In SaaS, it was, "You used to do things this way, and now you do things this way, and this is why this is better, and this is all the business impact."

With an agent, it's, "What do you want it to do?" Most people don't think about their work in terms of systems thinking: What's the goal of what I'm doing? What are the steps I need to take to achieve the goal? What are the tools, skills, and resources I need at each step? Who's in the loop at each decision-making inflection point as we progress toward achieving the goal?

Most businesses don't write things down like that. They don't think like that. Having these forward-deployed people allows you to do 2 things. First, integrate Legora into the broader tech ecosystem, so we have access to all the various tools and resources that we need to accomplish the goal. Second, leverage these legal engineers to say, "Hey, we know how an M&A workflow works in practice. This is how you do it before agents, and this is how you do it in Legora."

That's the hard yard, and that's where we spend a lot of time.

What level of contract do we need to justify an FTE model, which is more costly? It's human hours up front and margin reduction. What level of ACV do you think is needed?

Well, it's a great question, and people keep asking me why we raised so much money. I'm like, "Lawyers are expensive, man." We know we can afford to take this human, very human-centric approach right now, but we do it for pretty much anything in 6 figures and above.

You've got to really lean in and make it happen, because otherwise you're in danger of selling software that doesn't get used. We're very focused on adoption frameworks and making sure that if we sell you 10 licenses, you use all 10 and get a lot of value out of them.

And we can go to the metrics that matter: adoption frameworks. I do just want to ask, on the advice side, there's a lot of operators who are at traditional SaaS companies and traditional enterprise companies who are contemplating, "Should I move to an AI company? There's so much hype and buzz around them. I don't want to be left behind."

Mm-hmm.

Braze is an incredible company, but it's a traditional company. What advice would you have for those operators who are thinking about moving to an AI-first company and a next-gen company?

3. Should You Leave Traditional SaaS for an AI Company?

Yeah, for sure. I've become that person at Braze that people call when they're thinking about leaving and asking how I think about it. I've had this talk a lot with friends and colleagues.

The first thing is always: What do you want to do? I can tell you that working in this world is completely insane and unhinged, and it's all-consuming. So, you've really got to want to do it. You've got to want to lean in, and it's very different from traditional SaaS.

The pace of development, the pace of the market in terms of the competitive market, the competitive dynamics, and things like that—it's very different. You've got to really want to come in and build, figure stuff out, do things differently, and get a little uncomfortable. If you're okay with that, I'm always encouraging people to make the leap.

What's insane and unhinged?

If you think about the news that comes out every week—the competitive set, the model capabilities, who's buying what—there's so much hype around even just our space. Every time we win a deal or lose a deal, there's a PR announcement about it.

The level of pressure, the level of development, and then the product development specifically: The product from Legora a year ago, I thought, was incredible. I quit my job and joined the company. I was so excited about it. But that versus what we have now is night and day.

Your ability to stay on top of it, to learn, and to have that level of deep product expertise is really tough. You've got to take it very seriously in terms of enablement and education.

I can't remember if it was Logan or Chayton, so I'm going to give credit to both of them, but they said that you've been phenomenal in terms of bluntly creating a new playbook for this era.

Yeah.

I think what's challenging with what you said there, with the transience of models, competition, you name it, is that your playbook becomes relatively irrelevant.

Yes.

4. What Still Works From the Old SaaS Playbook and What's Dead

What remains from traditional SaaS playbooks, and what's useless now? What do we get rid of?

The 1 area I still like to ground my team in is that we want to be customer-obsessed. There's a guy, Brian Walsh of Force Management, who taught me this phrase: positive business intent.

If you're there and you're showing up, and you're genuinely taking the point of view that you're there to help—you're there to help transform their business, make a big impact, and help them win—I think people can feel that.

Be prepared, be professional, come with a point of view, understand their business, and do your homework. All the things that you would do from a preparatory perspective, you still have to do. You still have to prepare and take the point of view of understanding their business deeply, so you can understand the impact that you can make long-term.

That's still the same. But Braze never ran pilots. At Legora, we run pilots all the time, as an example. There's a tremendous amount of education you have to do because, as we were talking before the show, I think AI literacy generally in the market—not just within the legal context, but AI literacy generally—is very, very low.

And even when we're working with firms who have put a ton of investment and enablement into it, the models are developing, the capabilities are developing, and staying on top of it is a big challenge. We view part of our job as being that partner to help you stay up to speed with the cutting-edge technology and everything you can do with it. So, that part is quite different.

5. Demo Early: How Selling AI Agents Changes the Sales Motion

Totally get that. Does the traditional sales playbook of old work in a new AI world?

I think it's a blend. There are certain things you have to throw out, like the traditional—

Out?

The traditional SaaS playbook is that you don't want to demo. For example, the old-school SaaS thing was that the products weren't very good, so you wanted to hold the demo as long as possible, do discovery, build rapport, do all these things, and then demo on the second or third meeting. That's what the old-school guys would tell you.

With Legora and with agentic tools, you still have to do discovery and come with a point of view, but you have to use the product to show what the future looks like. Especially for us, in this category-creation moment, you're dealing with what they traditionally call unrealized pain. We're not typically replacing a tool. Occasionally we will be, but more often than not, we're the first tool of its kind coming into the organization.

You have to be able and willing to be agile, ready to ask questions, and then be able to pivot really quickly into building an agentic workflow off the cuff as you're talking to someone. That's quite difficult.

6. Legora at $5.5B: How Do You Justify That Multiple?

Can we actually use that as a way of explaining the valuation? I think people question the multiple. As we said, it raised a lot of money at a $5.5 billion valuation—I think it was post-money, which is public. But people are like, “Wow, that's why you have to assume a lot.” You gave me an answer before that I'd love for you to share, because I thought it was a good one. How do you think about that expansion from where we are to where we can be in terms of what likely Legora does?

If you look at the legal tech market, I think it's around $40 billion. That's the number I see floating around, depending on who you talk to. Legal tech generally is a $40 billion market. So, if you look at us and our competitive set valuation, that sort of doesn't add up.

But if you look at legal services more broadly, that's a $1 trillion market. Certainly, there's a bunch of work within that that isn't done by law firms. It's more rote, repeatable, document-extraction type of work. That's where we see ourselves really playing in the long term—not just in the legal tech market, but also in an element of the services market, where there's a high degree of application for likely Legora.

I totally get that. I want to go to the start of the funnel, so to speak, because, again, this was Chayton or Logan. I can't believe I'm forgetting it. Age, my friend. Age is a killer. You said it's insane and unhinged. It's the same for media, by the way. I'm in venture and media, so I'm double-fucked.

I know. The busiest guy in venture and media right now.

Honestly, it's a savage world. I can't wait for them to create an AI Harry. If Legora can do that, I'll pay double. But if we start at the pipeline, what's the biggest lesson in how to construct an effective pipeline in an AI world, and how is that pipeline-building process done?

7. How the Jude Law Brand Campaign Generated $50M of Qualified Pipe

This has been a big point of evolution for us. For example, we just did a big brand campaign with Jude Law. Before you do something like that, you have to do a ton of work in terms of the plumbing: What's our inbound lead scoring? How do we do data enrichment? How do we do lead routing and lead scoring from a probabilistic perspective?

There's a ton of infrastructure you have to put in place before you can really go big from an inbound perspective. On that basis, we've done a ton of work leading up to that campaign. Even last year, we were getting our systems in place, getting the territory assignments in place, and establishing all the rules and SLAs around leads—if we get a lead, you have to respond within this amount of time.

Even last year, from an SMB perspective, we had so many leads that we weren't able to follow up with as many of them as we wanted, in a timely way. The other thing was staffing. When I started, we were at 40 people. Today, we're over 500, and we still need more people and more systems to keep up with the demand.

How do you do lead scoring today? Is it simply based on the size of the contract?

Right now, you look at the size of the firm, the number of attorneys and compliance workers internally, and where they're located, and then you route it to the right team.

Okay, got you. Geography plays a role in that?

Mm-hmm. Yeah, we've got teams all over the place. In Europe, we have pods looking after every major market. For example, in Germany, we're doing so well that we just opened an office in Munich.

So, you run the GTM model. I'm seeing this more and more, where you have mini CEOs of each country. ElevenLabs has very much pivoted to that.

8. Sales Comp Multiples: 8-12x vs the 20x at ElevenLabs

Yeah, exactly. We've got Leo, who runs our European business, and then under Leo we've got a number of people from a country perspective, with a team behind them to execute. We have to be really cognizant that there's a lot of European data sovereignty and different regulatory compliance requirements. We have to have teams that really specialize in that.

I know you've got to get a permit to go to the bathroom. I'm sorry.

Exactly. Exactly. You've got to get my visa on the way in.

How do you know when to get up to go to the bathroom? You need a permit for that, too.

Yes. That was 25.

Can I ask how much Jude Law cost?

I can't say the exact number, but I can tell you it was worth every penny.

Was it? Okay.

Yeah, 100%.

Because people are going to watch this and say, “Harry's an investor and it's biased. I wasn't sure about it.”

Yeah.

Well, tell me it was worth it, and I'm thrilled because I want it to be.

Last month alone, we generated over $50 million of qualified pipe. That's not just inbound leads. That's pipeline that we talked to, qualified, and moved into a sales conversation.

Can I ask what it was the month before, to give us context on whether that's good or bad?

That was a pretty big jump month over month. I don't know the exact number, and I don't want to misquote, but we're seeing a ton of interest and demand.

I don't give a shit about Jude Law. I—

It honestly wasn't even necessarily for the folks who already know about us—the lawyers in the big markets know about us, right? It's more for the folks who don't. We just want that sort of brand awareness.

For us, we were late to a lot of deals. When we get into a deal, when we get into a pilot, we convert pilots 78% of the time into a closed-won opportunity. We're doing really well in terms of funnel progression, but the biggest challenge we had was just not being in the room.

For us, brand awareness is everything. The strength of our brand is better than ever. The Jude Law campaign wasn't for everyone, but overall we got really positive feedback, and the biggest thing is just brand awareness for us.

Super interesting in terms of brand awareness. I had Nick from Revolut on the show.

Yeah.

He said one of the biggest lessons he always had was that he thought brand awareness was fluffy shit.

Yeah.

And actually, it's one of the most powerful drivers of the business.

Yeah, and that's one thing that we report on to the board. Stuart and our marketing team have created a framework for how we score our brand efficacy in different markets, and we track that. We're making big progress, and we have a lot more coming.

Can I ask you, in terms of the pilots, the undeniable truth is that you're in a two-sided fight, or however you want to say it. It's you versus Harvey. How do you advise founders? I don't want to make this like Legora versus Harvey. How do you advise founders? Because there are a lot of markets where it's Brex versus Ramp, or Stripe versus Airwallex, or whatever. How do you advise founders when it's one versus the other, when you're in that sales process?

At the end of the day, it comes down to preparation and execution. One of the companies I really admire and try to model ourselves after is Ramp, like you said. We talk a lot about them internally in terms of how they've built the execution layer from a go-to-market perspective.

If you talk to anyone who's engaged with a Ramp sales team, they're always prepared. They don't have to take things back to get answers, right? There's a degree of professionalism and preparation that goes into every conversation.

Also, so often in go-to-market, people talk about using AI to automate different processes. “I want to update my opportunity notes and draft this email.” Of course, we do all that stuff. But the other thing that people don't think enough about is how you're using AI to deliver more differentiated value from a services and insights perspective.

We have a lot of data from pilot participants. How can we give insights into that data that are going to help the firms and companies that we work with make decisions around adoption frameworks, ROI, and things like that?

So, if I'm a founder listening to this, what does that actually mean? We use pilot data to then encourage net-new customers. We say, “Hey, 84% of people that use this type of email actually convert better.” What is that?

Yeah, exactly. Within a law firm context, for example, we'll segment out by practice area. Let's say a big firm has 10 practice areas, and then you have X number of people within each practice area. We can report out on consumption and usage by practice area.

We also track and create frameworks and use-case banks for actual applications and workflows that we're building. Let's say, within that example, we've got 10 practice areas and 7 of them have really high usage. We're creating and capturing new use cases, and we're sharing that back with them on a regular basis, but maybe there are 3 where we're not.

You can start measuring things like: Did the quality of your work increase? Did you decrease the amount of non-billable work that your associates were doing? Were you able to attract more talent using a tool like Legora? People get excited about using the latest and greatest in AI.

If you take that and apply it to the 3 practice areas where maybe we're not doing as well, we can show them insights into who's really leaning in and who isn't, and where we need help from a change-management perspective.

Totally. Okay, that makes sense. One is execution and being prepared. Anything else on how to navigate that? Say we're looking at Brex versus Ramp, or Harvey versus Legora. One of my biggest bits of advice to founders is always to be respectful. Knocking your competition is not part of a sales process.

Yeah.

Sell yourself; don't bash them.

Exactly. We try to stay in our lane and focus on ourselves. Obviously, as you mentioned, we have one big competitor, and they come up on every deal. It's a death match on every deal. It's super competitive.

We have a ton of respect for them. No one over at Legora is thinking that every deal we're going into is a cakewalk. It's the exact opposite. They're very good and very aggressive, and we take them extremely seriously.

We screen for intelligence, we screen for effort, and we screen for competitiveness. At the end of the day, if you really want to win, you've got to go out-execute, not deliver, and evolve your playbook. We run pilots very differently now than we did a quarter ago and the quarter before that.

That's interesting. How do you run them differently today than you used to?

We have a lot more tools. We have a lot more reporting. We have a lot more specialty in terms of implementation and change management.

Going back to the firm context as an example, you can't just have a litigation attorney go talk to an M&A team. You've got to have an M&A attorney go talk to an M&A team. As we've scaled out from just me to a much bigger team in the US right now, we've hired specialists who focus on different areas of the law and who can, again, get in bed with our clients and the folks in pilots and build those bespoke workflows for them.

We're able to do that. We're able to get on-site. Getting on-site is super critical because people don't pay attention on Zoom. We all know that, right?

When you say “getting on-site,” what do you mean? You mean in the sales process, like, “Hey, get into their office”?

Yes. I encourage every GTM and every legal engineer: if you're not in their office by the second or third meeting, something's wrong. Certainly, some companies, especially on the corporate side, may be hybrid or remote, so you can't always do it.

But, in particular, for a deal of really any size, at the end of the day, for firms, this is sort of a bet-the-company-type decision. This is an existential decision-making process. From that perspective, you're going to bet on the team just as much as you're betting on the product.

At the end of the day, you're betting on a team that's going to meet you in the future with the solutions and adoption frameworks that are going to help you get there.

It is about the decision, because this is that core investment in the AI technology field, if you look at it from the partnership perspective as a law firm. With that in mind, and with the stickiness that can come, how do we think about giving it away for free and reducing margins in order to gain market share?

Yeah, we don't give Legora away for free. We try to have price integrity. We try to be very transparent around what our pricing model is and how we go after things. But in a competitive dynamic, we do face that from various competitors.

Do they all give it away for free?

They have.

Yeah.

Certainly, from our perspective, I always make the joke when I'm talking to folks in a competitive dynamic. When you're getting down to the decision-making process, you're focusing on the product score from the pilot, the commercial model, and the roadmap.

One thing we do is what we call the “8 Mile talk track.” At the end of 8 Mile, he just says everything that's wrong with him, about him, and his family. We just say, “This is exactly what's going to happen if you pick us. This is what the counter is going to be. This is what they're going to go to at this point.”

We have a pretty good point of view on what will happen, and it usually does. From that perspective, we just try to stay ahead of it.

Do people churn when they're embedded in a product? If switching isn't frequent and it's supremely sticky—and I imagine, Patrick, an easy one—I just say, “Let's give it away for free to everyone for the first year. Let's get everyone on it for free and get them as embedded as possible. We'll tell all of our investors that our margins are going to suck. There's no revenue. It's going to suck. But next year we're going to be at a billion five in revenue.”

Well, there's one way to look at it, but the way I think about it is, first of all, if a company isn't spending any money on a product, does it matter? They're not going to put the resources and attention into it that they need to.

We really need our customers to lean in and want to change. At the end of the day, we can have the best team focused on all the right things, but if the customers aren't leaning in, then it's going to be tough. I think going to zero is not helpful in that dynamic.

But I see what you're saying, and we do try to be easy to work with. From that perspective, we try to be as flexible as we can be.

It's a very interesting behavioral economics study: they gave away a yoga class for free in a park, and it had a 52% attendance rate. Then they charged $35, and it had a 92% attendance rate.

Exactly. Yeah, exactly.

It's like, people commit to what they pay for.

Exactly. Exactly. You have to have value. You place value in your partners, and we find that to be true.

Well, I interviewed Winston & Strawn, and I thought one of their GTM approaches was very smart: using PE as this kind of expanded funnel into the clients that they have in law. How do you think about that?

Yeah, that's definitely an angle. Certainly, within the legal-services ecosystem more broadly, you look at the influence on decision-making on tooling, for example. If you're selling to a corporate, they're going to ask all their law-firm panel what tools they're using. If you're selling to a law firm, they're going to ask their big corporate clients what tools they're using.

And certainly, private equity—

The power? Do PE firms have the power over the law firms, or do the law firms have the power over PE?

I think it depends on the firm and depends on the PE company, for sure. But there's definitely a lot of interconnectivity. One of the most fun things about selling into this market is that every deal is very different.

Selling to a law firm, there are a lot of personalities. Stakeholder management can be very different from firm to firm.

So, there are innovation teams, knowledge management, and partners. The degree to which partners want to lean in and get involved—and then there are AI committees, subcommittees, and all these different things. It’s very intricate, the decision-making process.

One client of a firm might have an outsized voice at the table, for or against you, as an example. You have to be very mindful of that. That sort of map is very complex.

That has many different client processes. Biggest lessons or advice on lead scoring, going back to that? Anything you see people doing way wrong?

The one thing that remains true is that the longer you let a lead sit, the worse the conversion rate is, right? We try to optimize for the highest-intent signal with the fastest response time.

We’ve automated a lot of that, from sending out the calendar invite for the initial call on the right system with the right person. We just try to be as fast and as accurate as possible at that. I don’t think we have any big insights on that.

No, dude, it’s exactly like a deal. When you say, “We’ll see you in 2 weeks,” it’s like, “I don’t know what…”

Yeah, and if you miss something or something gets dropped—and this happens to everyone—then your chances of converting that go way down. That remains true, and I don’t think we have any big insights on that.

We have that. Cool. You’re advising me: I’m an early-stage founder. What’s your biggest advice on sales qualification? What are the hard questions to ask, what not to ask, and what’s the way to do it?

For us, it’s a couple of things. Going back to the pilot example, one thing that we’ve learned is that we’ve had some firms say, “Oh, we have this really onerous infosec process. We want to do a pilot, but we don’t want to go through infosec, so we’re just going to do it on test documents or publicly available things.”

That’s a recipe for low engagement, low excitement, and it generally doesn’t work out well. You’ve got to have a little bit of give and get. There is a little bit of pain on the front end in identifying the use cases that you want to test and the stakeholders that you want to be involved in the pilot.

You have to go through—as you can imagine, working with Deloitte, these big law firms, and EY—the infosec process is nontrivial. If you can get buy-in on identifying the success criteria for the pilot, who’s going to be involved, what use cases we’re going to test, and what metrics are involved, then you can go through that initial, somewhat painful period and know that you’ve got something there.

9. How Legora Gets Access to Senior Stakeholders So Easily

How do you bring in people with true buying power? I imagine they’re not always on the first calls. How do you make that transition of, “I’m so pleased, Patrick, that you’re excited about Legora. Can we please try and get your boss in now?” Because I want to progress this.

I have to say, one of the things about Legora that’s floored me is that at Braze, we had this problem. At Braze, the executive buyer was the CMO, and getting access to a CMO was so hard. We would get it done very, very rarely, and we always bent over backwards to make it happen.

With Legora, because there’s so much chatter in the market about AI and the firms and corporates both want to understand what others are doing, we actually get access to power pretty easily. People want to learn.

On the law firm side, they’re getting asked by their clients, “How are you using AI? What tools are you using? What are the use cases? Where are we going to see this value in our bill, for example?”

On the corporate side, they’re getting a ton of pressure from the board and the CEO: “Hey, go figure this shit out. We need to optimize XYZ process and AI everything.”

We get access to senior stakeholders who want to lean in and learn from us. But typically, if you don’t have that access early, to your question, what we try to do is focus on the highest-value use cases and highest-value impact as quickly as possible. You want to grab attention really, really fast.

Lucky for us, the Legora product’s awesome. Coming in with a perspective on the company and the role, based on the ICP that you’re talking to, talking about some of the high-value use cases that we have, learning about what’s most important to them, and then showing them how we’d solve that quickly—they’re like, “Wow, I want to show this to my boss.” That’s generally a framework that’s been successful.

I come from an industry that is traditionally called sheep-like. How do you follow others? I don’t understand why anyone would attribute that to us. To what extent is legal a sheep-like industry, where it’s like, “Oh, Clifford Chance, Slaughter and May, you name it, use X”? To what extent do they follow others?

There’s certainly an aspect of a flight to safety during these category-creation moments, because this is all new. The general understanding of how agents work, how AI works, and how to think about use-case design is still being developed. The executive buyers at the firms and at the companies generally aren’t as up to speed on that. Some of them are, but broadly, probably not.

There is this flight to safety. Generally, people want to feel like—you never got fired for hiring IBM. At the end of the day, there is definitely an element of that.

Do you not feel both you and Harvey are IBM at this stage?

I was going to say, last year, we were the new entrant. We were trying to make our name, and we were definitely not IBM last year. I think at this point, working with the firms that we work with, having likely Debevoise, Linklaters, and other big firms advocating for us really goes a long way. I think we have that stamp now, but that’s been a journey that we’ve been on.

You’ve got 20 of the Am Law 100, yeah? And Harvey’s got 40 or 60?

I don’t know their numbers, yeah.

I think they said 50 of the Am Law 100.

Yeah, 50.

Does that mean we’re fighting over the next 30, or does that mean we’re fighting for each other’s clients?

Both.

It does.

For sure. Yeah, they know who we work with, and we know who they work with. We’re both trying to get in. We’re very aware that they know who our customers are, and we know who theirs are. We’re both going aggressively after them and also scaling up quickly to go after the next 50, or whatever the number is.

We’ve got to play defense and offense at the same time, and that’s what makes it fun.

God, the old SaaS world feels quite nice.

Yeah, exactly. It’s like 30% growth a year and quarterly release cycles.

Do you guys pay attention to social? Because for VCs, no—but you saw it last week. Paul Graham tweeted, and then Matt Miller tweeted back. I’m not saying anything about either individual; I like them both immensely. But does it impact the team?

I don’t know how much it impacts the team. We definitely hear about it. When PG tweeted that, my phone blew up. Shout-out to him, by the way; that was awesome.

I heard it, dude, by Schulz everywhere[?]. He’s a guy after my own heart.

Yeah, even in Scandinavia. I try not to think about it too much, and obviously, we’ve got Chetan and others really advocating for us in the public sphere. We really appreciate that, but I leave that stuff to them. I’m not on Twitter.

Do you bring VCs in to help you win deals?

Definitely.

That’s interesting.

100%. The cool thing about the space that we’re occupying is that the VCs themselves—if you think about ICONIQ, General Catalyst, and Bessemer—they have huge legal networks themselves. They’re big spenders on legal services more broadly, so they definitely have big networks and are advocating for us whenever they have the opportunity.

Certainly, our competitors do the same thing, and that’s definitely an element of these sorts of opportunities.

I always tell founders that I work with: use your cap table as a weapon.

Yeah.

Absolutely.

Exactly.

What does Harvey do better than you, say?

That’s a good question.

It’s a hard question.

That’s a hard one, and I don’t want to give—I don’t know if I want to give an inch at all. Certainly, the strength of their brand is something that’s hard to deny. They’ve done a great job. They were the first entrant, and they’ve built this amazing brand. Kudos to them.

When we said earlier about the playbooks, again going back to something that Chetan said, he said training in particular is something where we’ve done incredibly well in ramping people. What’s the biggest lesson on how to do training well? Because it’s not easy, actually.

This is another thing as a leader that’s very different than in the SaaS environment.

How so? Because I thought talent development would maybe be the same.

Well, yes, but in the SaaS world, it’s much more predictable and on this very clear, slow operating model.

So you had your quarterly releases with some monthly shipping in between. Ahead of the quarterly release, you've got all this documentation, and you do a big certification; you go through all these programs. With Legora, we do big, huge product things every week, and the team has to stay on top of that. There's no way you could do a global certification program for every big feature we launch in real time, all the time.

And so we have to do a lot at a team level and regional level, and we do a lot asynchronously with video content. We use Notion really heavily. The product teams really embed with the individual sales and legal engineering teams and engagement folks to make sure that we're all up to speed, but you can't do it all centrally. You have to really distribute through both asynchronous video and Notion content, as well as team-level enablement. So we activate our product guys in that way.

Can I—don't worry about being too specific—how does that look for sales training? For the first week, what do I get? Do I get a Notion link and a load of video libraries?

No. So this is actually something we've really elevated and something I'm really proud of. When I first joined, Vilgot told me to go to Best Buy and buy an Apple computer, and then I went and had a couple of videos of Max doing a demo. Now, every 2 weeks, we have a new-hire class. At this point, it's between 40 and 50 people joining every 2 weeks.

We send everyone to Stockholm for 5 immersive days. This isn't something where you're just going to go do a couple of video things and then walk around Stockholm. This is intense and immersive. We expect GTMs and LEs to come out of that week ready to go. From a ramp perspective, it's a straight line up. We expect to drop people in and see them be very productive very quickly.

When you say ready to go, you mean they're ready to sit on calls on their own with clients?

Yes.

That's quick.

It's very quick. I had a guy, in his second week, do a demo with one of the biggest companies in the world, and he killed it. Obviously, I joined because of the nature of who the company was.

Now, Patrick decided to sit down.

Yeah, no, I was there for guidance, but we expect productivity to happen very quickly.

Sorry to be specific, but there are so many founders who listen literally with notes. What does an immersive first week mean?

We have a cross-functional education program focused on everything from our sales stages, our opportunity cycle, and our entry and exit criteria. We do a full day of demo work. We have a huge library of Gong and video content from a demo perspective, but we also do a lot of role-plays. We do a lot of education on the market generally.

Because we hire a lot of lawyers, we also hire a lot of technologists. The lawyers have to train up on how the tech stuff works, and then the technologists have to train up on the subject-matter expertise from a legal services perspective. We have a ton of content on industry education, product education, and the competitive landscape.

The competitive landscape, as mentioned, changes every week. So we have to update all the product information and the new product information. We basically have a university-style 4-day program where every department comes and enables the new hires on that particular program and how we operate. We have all that available for them in the new-hire Notion. Then all the reps have their own personalized ramp page where we track all the metrics that we're looking at from a ramp perspective.

Of the 40 to 50, how many do you think make it?

That's a good question. When we move on from sales folks, we do it typically within the first quarter. We actually have really high retention rates relative to the market.

What are the signs that someone's not going to make it?

We score demo quality using AI. We use Gong, and then you can create a scoring mechanism for how the call went. How was the discovery framework? What was the demo flow, and so on? When we get a red flag on that, our enablement team goes in, looks at the call, and does a playback with that person.

If you look at call-quality scoring plus opportunity development from a pipeline perspective, you can see pretty quickly who's tracking. We know what good looks like and what good doesn't look like, and you can see pretty quickly within about 45 days.

So, is it debunking, then, the traditional notion that, “Oh, well, you know, enterprise is really difficult to understand whether someone's a good sales rep because the sales cycles are long”?

That, from a traditional SaaS perspective, might still be true. With us, even our enterprise folks, when they come in, they're going to be buried in deals within 60 days. Our best people are closing deals typically within 90 days, even on an enterprise team.

From that perspective, we're very hot right now. This market is being made right now. It's not like you have to go take your territory list, get your BDR, go do some account-based marketing, and get the initial meetings. That's traditional. I've run cold territories before, and I've managed teams that have done that from a SaaS perspective. This isn't that. This is one of the hottest markets of all time.

When we drop GTMs into their book, they're into pilots—typically something like 5 pilots within their first quarter. We're asking people to get very productive very quickly because this isn't something where we can do a bunch of hand-holding for a long period of time.

We have so much inbound and so much interest that you know quickly, because the volume of opportunities that they're working is much higher than it would be in a traditional SaaS environment.

Would you rather hire someone who has experience selling to law firms or someone who has experience selling this size of deal?

I would rather have someone who has experience selling this size of deal.

Really?

Because legal tech, traditionally, we're selling much bigger deals than traditional legal tech companies.

ACVs like 250, 500?

Around that. It depends on the segment, but roughly. We're doing a lot of big, high-7-figure deals. A lot of legal tech companies were more niche, and so the ACVs and ARRs were not what ours are.

We have hired some folks from legal tech, and some have done really well, but they're not used to sending a million-dollar proposal across the line. I'd much rather have someone who is really strong in understanding organizational dynamics and change management, and was really confident in sending large proposals and being able to work that sort of angle.

What was the hardest deal to win, and why do you think you won it when you reflect on it? A win postmortem.

I'm thinking about one right now. I don't know if I want to say the name, but it's a big, global law firm that we won.

How big was it?

It was a medium 7-figure deal.

Wow.

Yeah. For us, it was hyper-competitive. It was global, so we were using the full force of our global team in the US, Europe, the UK, and Australia. We had all 4 regions activated, working this from a pilot perspective. It was very close. There was influence on both sides. Do you know when it's close?

Yes. How?

This is how we knew how close it was: it came down to an executive presentation with our CEO and their CEO in front of their executive panel. That's how they ended up making the decision, and we won.

Oh, I would be nervous if I were Max.

Yeah, dude, he's an alien.

You want to be on form and sleep well the night before.

Honestly, the biggest thing we have going for us is that we have Max and no one else does. We feel he inspires a lot of confidence.

Is that very rare, to have a CEO-to-CEO bake-off?

It is. In my career, yes. But in terms of the Legora experience, no, because these are such important decisions.

If you're a top law firm, I don't think it feels unreasonable.

No, you want to know who you're betting on. You want to have a deep level of understanding of who they are, what the vision for the company is, whether it aligns with your vision, whether it aligns with your values, the product strategy, and execution.

People really want to get into the nitty-gritty and understand not just Max and myself, but the team more broadly and the chops of the folks who are going to be delivering the services. They look at all of that. It's a really fine-tooth comb that they go through the stuff with.

Okay, dude. Everyone has a flip side. Take me to a deal you lost. When you look back on it, what's the postmortem? What more could we have done?

I'm thinking about one right now, and with the enterprise, it always goes back to multithreading and who you get to and who you don't.

Within a law firm context in particular, the decision-making is sometimes opaque. There are often these panels. Sometimes, let’s say there are 5 people on the panel, and sometimes you get to meet all 5 people. Sometimes you meet 4 or 5; sometimes you meet just 1 person in terms of one-to-one engagement and relationship.

There was 1 key member of the panel that we never got time with and weren’t able to build a relationship with. Oftentimes, with panel decision-making, the loudest voice gets what they want, and we weren’t able to get that. That was really painful.

Are the days of steak-buying dinners over, or actually not?

It’s not like it used to be. Back in the early days—I graduated college in 2008—and that was still the era of steak lunches, steak dinners, a lot of entertainment, and sales. It’s definitely evolved.

I think more so these days, people want to do activities. They want to get out and maybe not go to a steak dinner, but do something a little more fun.

Oh God, it reminds me of mini-golf days.

Yeah, well, not quite like that, but relationships are still really important. Certainly for us, it’s actually conferences. There are so many conferences and so many events, and any chance we have to show up and show off our team, we take it.

In traditional tech, I think there’s been a realization that what’s most helpful for our business is actually being a brand logo on viral podcast clips. That’s the new gold.

Yes.

Having a banner at a conference that no one really wants to go to, not so much. In traditional tech, is that not the case in legal?

Legal tech right now is having this renaissance. There are so many new players and so much money coming in. But going back to the conference point, you can waste money on conferences and you can make money on conferences, and it sort of depends. We’ve got a pretty good playbook for that.

What did you spend money on that was an absolute banger, and you learned something from that that I should know?

When they go really well, it’s these fireside-chat-type executive dinners. We hosted one with some of our investors. Their office is at Zero Bond in New York.

One thing that’s true is that everyone still wants to go to a fancy restaurant and hear someone smart speak. We still find that these thought-leadership, AI thought-leadership dinners are super effective. They cost a lot of money, and you have to get some talent in the room from a thought-leader point of view, and then have them do a fireside chat with Max. Those are highly, highly effective and something that we do very often and really well.

What have you spent money on where you’re like, “Guys, I can’t believe we fucking spent money on this”?

Going back to the conference thing, I think we averaged 1 conference a week last year. We showed up at every conference you could think of. Some of them we repeated this year, and some of them were like, “We’re never doing that again.”

I love that. Speaking of, we said that: would you rather have someone who’s versed in law or someone who’s versed in deal size? When you think about incentivizing teams, I think sales comp packages are really hard to get my head around.

Yeah.

Traditional SaaS, going back to traditional versus new world: 4x OTE, good. Then I have Baker from Clay, who’s at 6–7x.

Yeah.

And then I have my dear friend Carlos from ElevenLabs, who went very viral saying 20x. Then I’m like, “Oh my God, I feel like such an insignificant human being.”

I heard that 20x number and got so many pings. I mean, I obviously follow the show.

Pings every single week. You got so many pings.

All my friends who are in this business were like, “Wait, what’s your multiple? Did you hear this guy?”

10. From $3.5M to $100M ARR: The Growth Story

Everyone got that. I feel a little bit bad for the rest of the CROs. How do you think about effective sales comp setting today?

To start off the top, ours right now depend on the market, the segment, and the region, but ours right now are between 8x and 12x. That’s where we landed. We don’t just take a multiple and apply that to the competitive-market OTE. You’ve got to really take a bottoms-up approach to it and look at all the metrics we were just talking about before.

Look at ramp time, productivity per head, ARR per head, and pipeline evolution within certain territories. We did a bottoms-up analysis of that last year and got to that range, but we also had a year last year where we absolutely blew out every metric that we put in front of the team. I don’t know how effectively we’re doing that, but that’s how we’re doing it right now.

You think 8–12x today is where you sit, which is good.

Yeah.

What percentage of people should hit that?

Our average attainment last year was 280%.

Wow. Is that an effective attainment setting?

Yeah, that was a bad job by me. No, I mean, when I started—just going back for context—we were at $3.5 million, and Chetan and the Redpoint guys were like, “Can we do $25 million?” And that fell.

I remember giving—we had raised our Series B—and I remember giving a big rah-rah speech. We had everyone in Stockholm and did a big rollout.

You did it.

Yeah, we—

I’m a VC, so I give credit to other VCs for a living, but I give credit to Logan on that one. He paid up in advance for something that wasn’t that obvious, respectfully.

Uh-huh.

And credit to him.

Yeah, absolutely. He got me. That’s how I got connected with Max, through Logan. He actually introduced me to Brex as well, so I’m always a big fan of the Redpoint team.

Sorry, you joined when it was around $3.5 million?

Yeah, the $3.5 million. But then we were like, “Okay, can we do $25 million?” I remember we were at around $7 million, we raised a Series B, and we had everyone in Stockholm. I was giving a big rah-rah speech to the global team at that point, which basically fit in the kitchen of our Stockholm office.

Obviously, we hit $25 million in Q3, and then we went nuts in Q4 and blew through every metric. We ended the year at $70 million and then obviously crossed $100 million earlier this year.

The projections are very hard from our side. From a forecast perspective at the beginning of the year, I only gave guidance to the board based on a rolling 6-month basis. At this point, based on the data and the pipeline analysis that we have, we feel pretty good about our ability to forecast the top-line business.

The individual productivity stuff can be a little all over the place because there are obviously bluebird deals that happen and things like that. We also have a ton of intra-quarter open and close, so being able to forecast that is a little bit of a pin-the-tail-on-the-donkey challenge. But we’re getting better at that piece of it.

11. How to Do Forecasting When the Market Is Elastic and Unpredictable

What’s your biggest advice to other CROs, when you look at the CROs who ping you about the 20x that we discussed? What’s your biggest advice to CROs on how the fuck to forecast effectively in this very dynamic landscape?

It’s really hard, and the first thing I say is you’ve got to have a little grace with yourself and set expectations appropriately. In this market, it’s been relatively elastic so far, and that won’t continue forever, but right now that’s the experience that we’re having.

I do 2 things. I do a rep-and-manager commit roll-up—bet your life. You have the rep roll-up, the first-line manager, and the second-line manager.

What does that actually mean? I’m sorry for being—what is a rep roll-up? What does that mean?

If you’re a sales director at Legora and, let’s say, you have a team of 8 people, you go to all 8 people and say, “Bet your life: how much ARR are you going to close this quarter?” It’s that level of seriousness.

Then that manager takes the rep roll-up and commits to whatever number based on that input from the reps. The directors take that to the VPs, and the VPs take their director roll-ups and commit to a regional number.

Right now, including India, we have 5 regions: APJ, India, the EU, the UK, and the US. I take the VP roll-up and compare that to the weighted forecast.

We’ve got this amazing woman in our RevOps team, Lulu, who I worked with to create this weighted version of what a weekly, monthly, and quarterly forecast would look like based on the opportunity stages. With that, you have to have really, really tight rigor around opportunity management. The stages and the amounts on the opportunities have to be really dialed in and updated in real time.

Last quarter, the regional rep roll-up and what we call LuluCast—the weighted version, or what I call the math version, of the forecast—were the same. We were pretty accurate on both.

Where do stages go most wrong?

If you don't have really good entry and exit criteria that you can explain to your grandma.

What does entry and exit criteria mean?

In our sale, let's say, if you think about a sales process, there's a two-sided buyer journey, right? There's the funnel on the way in to close one, and then there's the funnel on the way out as you look for advocacy and adoption. On the way in, let's say we have 5 sales stages. For example, I mentioned the pipeline that we generated off Jude Law.

To get into qualified pipeline, you have to go through a discovery call where we ask questions around the buying process, what they're looking for, what they're interested in, and things like that. Then, to progress that to the next stage, certain things that they say have to be true. They have to be in a buying cycle and have budget. You can think about BANT frameworks: budget, authority, need, and time.

As you move into the qualification criteria, it's, okay, the next stage is the pilot. What do we need to do to get into the pilot? As I sort of alluded to, it's executive buy-in, infosec, budget allocation, and things like that. If you get that right and have consistency across the global teams, then typically the forecasting is right.

If you get the right weighting based on your funnel progression historically, then you can get to a weighted forecast that's directionally accurate.

You said there about the different regions that you have.

Mhm.

If you were advising CROs and CEOs today, do you have to be everywhere all at once today?

Yes.

Mhm. That's different.

It's different. The speed at which we're doing it is very different. Going back to the Brex experience, in New York tech, we had a London office. That was sort of the next move, but it took us a really long time, for example, to expand into Germany, which we eventually did.

Expanding into Japan and other places took time, whereas we've just opened in Germany, we've just opened in Spain, we've opened 5 offices, maybe 6, in the US, Sydney, Bangalore—we've been all over the place.

India feels like a strange one. It's just such a different universe. What was the thinking behind India, and how's India going?

We typically follow the ball in terms of pipeline. From that perspective, we had a ton of initial interest. We have great interest in the Middle East, and we have great interest in India, so it was a ton of inbound signal.

Where's the hardest? Again, Carl Eschenbach has spoken about Japan and South Korea. I'm friends with Daniel Dines from UiPath, who always says that that's a difficult region. Where's the hardest?

That region is very hard, and we've been consulting a lot of our investors and advisors on how best to enter those markets, but I would say APAC is probably the most complex.

Certainly, each region has its own nuance with respect to data-hosting requirements, processing requirements—you can't process stuff in Europe or the US; you have to process certain things in-region. Some of the model providers don't provide access to the models in certain countries. For example, if you're selling into China, certain model providers don't provide access to the models in China and other places.

There's definitely some architectural work that goes into it, and there's a ton of work we're also doing. We announced today a big project we've done with McKinsey, focusing on European public-sector work. If you think about FedRAMP in the US, there are all kinds of things that are really hard from a technology perspective that you have to keep in mind.

With the greatest respect, and forgive my ignorance, sovereignty is kind of an interesting word that's thrown around. But to what extent do you see Americans choosing Americans and Europeans choosing Europeans? Is that a thing?

It's definitely a thing.

It is.

It's definitely a thing. Certainly, we have the perception when we come into a deal that people think I'm from Sweden, for example. A lot of people do.

You look Swedish. Seriously, you could change your name to Sven and probably be that. Just don't talk.

It's like the guy from Frozen, yeah.

So he's mute.

I was joking: the LLMs we use are all American. But, yeah, that's definitely a thing that we deal with, particularly in Europe, obviously, with a lot of the geopolitical stuff going on. In the US, people really care about understanding jurisdictional context and things like that. So it's a big thing.

We spoke earlier about the hardest challenge, and you said it was just the speed and the velocity of scaling.

Yeah.

What breaks that people don't see, and what are the lessons from that?

Things like the plumbing and RevOps of how you do billing and your billing systems. If you want to change anything in your pricing model or your billing system, and you're adding as many customers as we are every month, it gets very hard to do things like billing systems, reporting, and all that stuff.

A lot of it gets done manually at times because if you're changing from one system that worked for you at $10 million but doesn't work for you at $100 million, you have to make those changes. We migrated our CRM to Salesforce, which is awesome. But anytime you do a CRM migration, it's a huge pain in the ass.

So, you migrated to Salesforce. What did you migrate from?

I don't want to say, and I don't want to speak ill of it, but it wasn't working for us. I did a full survey of the market, and we picked Salesforce. Anytime you go through a systems change like that, there's change management, but there's also opportunity management—different ways of working that are really hard to roll out and that you have to get right. But people grumble.

Do you think Salesforce faces the threat of becoming a database that agents crawl on top of, with which you have no interaction or engagement?

I think all the traditional SaaS companies are definitely under threat right now, but I have to say I've been so impressed with Salesforce. If you look at it, they did a hard “break glass in case of emergency” pivot last year, and at their scale, they went full agentic in their go-to-market framework and positioning.

Credit to them for being very early on that, ahead of every other big tech company. I don't know how it's going to shake out, but I know we did a survey of all the other hyper-scaling AI companies, and most of them are using Salesforce.

If there's one CEO you would back to shift and change with the landscape, it would be Benioff.

Yeah, 100%. Like I said, anytime the words Benioff and Davos came up in a deal review, you knew you were pretty fucked.

Benioff, which I actually see in Max: Max will get on every freaking plane to close the deal.

Yes.

To close the deal.

100%. You have to have that right now. Max basically lives on a plane. I mean, I ask you candidly. You see guys like him leaning in.

I think Max is one of the, I would say, pretty great CEOs, and we're very lucky. What does no one see about Max that you think makes him special?

I think he leads from the front. He's always up early, online, pushing the ball, and setting the tone for the team. As a leader, he's someone who is going to get on the flight, take the call, jump on an escalation, call into a deal—he's going to do whatever it takes.

I think that permeates throughout the organization. But he's also very kind, and he cares deeply about the business and about building the business in the right way. He wants to build a business that's remembered, with a culture that made a big impact on the people who work there.

He's very focused not just on Legora being successful, but on all the people at Legora developing their careers and taking that next step. He takes that stuff really seriously, and we work on that as a leadership team.

Any lessons on culture at scale?

That's one of the hardest things. When people ask me what's hard, maintaining the culture that we have as we add the number of people that we're adding is very difficult.

Funny enough, I have this now where I don't have time to say hello to everyone internally. I used to come in when it was under 20, and I could literally go around and say good morning to everyone, which was nice. Now I can't, and I find that really weird, which is pathetic given how tiny it is compared to you.

But that's a weird one for me. Anything that you learned, know, or do?

Our cultural values are LFG: lean in, grow together, and fight for excellence. From a cultural perspective, I think it goes back to just being intentional. You have to repeat what your values are, highlight what good looks like, and constantly reinforce your expectations around cultural ways of working.

One of the things I always say is that we're big on no assholes. The biggest way to get on my shit list is to be disrespectful to someone internally or, heaven forbid, someone externally. Living our standards and constantly reinforcing what those are is something that we spend a lot of time on, making sure that we're building the company the right way.

And that's why Max never hired me. Can I ask a weird one? Is everyone talking about token maxing now? For you as CRO, you're the man holding the budget. How do you think about encouraging AI usage internally, token maxing, token budgeting—anything that CROs of the future will need to contemplate or consider that they're not today?

We're pushing our teams to use AI in every aspect of the deal as much as possible. Thankfully for us, budget isn't a huge concern at the moment, so we're really focused on automating the difficult work.

Difficult? What I mean by that is, as the man with the budget, I don't want people to know that I have a lot of budget.

Yeah, well, it's more around my expectations. It's less around the budgetary questions and more around the fact that we have access to a bunch of different AI tools. We've created playbooks for things like account planning, as an example, where we've created an agent that can do a one-click account plan and help you do meeting prep for use-case development and things like that.

It's more about being really specific: We expect you to be using these tools. Here's the stuff that we've built from a central-team perspective, but I also expect our teams to be going out and building their own stuff and elevating the game. Again, we can't do things the same way that we did things last year and expect to be successful moving forward. I want them to share that stuff broadly, and we highlight what good looks like on all of our global team calls.

Are you seeing non-engineering people building their own tools?

100%.

Really?

Yeah, 100%.

In what way?

We have legal engineers, for example, who will have a product idea around something that we should build in Legora, maybe for a specific industry. We have a funds attorney who works with us who's excellent, named Felix. He had a perspective on some things we could build for our private-equity clients that would be highly impactful.

He was having a hard time describing the requirements to our product team, so he spent a weekend vibe-coding a version of what he thought would be impactful and showed it to the team and to me. It was highly helpful in understanding what the vision of the product could be. That's an example.

Final one before we do a quick fire. I know budget's not necessarily a constraint, but it always is slightly. You have to keep it in mind.

For sure.

What would you do if you had unlimited money that you're not doing today?

It's less about money and more about time. The hardest thing we have right now is taking the time to pause and think about ways of working and our operating model. I'd love to, for example, do a 2-day boot camp where we bring in some AI experts and go through every part of every process of every go-to-market team and every motion, and build more automation and more agents to do more things—to take that rote work off my team's plate so they can focus on those things that have the highest and biggest impact.

It's more about time than money right now. Taking that time to think strategically and get everyone together in person has so much value. We did our sales kickoff at the beginning of the year in Stockholm, and there was so much learning and so much relationship building that happened. I wish we could do that stuff all the time.

The speed of development of our business means we don't have time to get together in that way, and that's something I wish we were able to do a lot more of.

Did you ever doubt whether you were able to make the jump to next-gen CRO?

Yeah, definitely.

How do you get comfortable with that? I face it every day as an investor, where what was good is no longer good. Legora's growth is unparalleled. Before, it was 1 to 5. You're forced to think through, maybe we need to be energy investors, maybe we need to be infrastructure investors. And you're struck with this: Am I good enough to make the jump? How do you reflect on that?

For me, it's more about being super intentional about what I want and my vision for myself. Honestly, people ask me, “What do you want to do next?” I'm doing it. This is what I've always wanted to do. The job I'm doing right now is the job I've wanted to do for a really long time.

But more often than not in this world, it's more around whether you bet on the right horse. I took a bet after leaving Braze and went to another company, and it didn't work out. I was working really hard. I was doing all kinds of things that I thought were smart, and we just weren't seeing the results.

Then you come to Legora: right place, right time, right market. So much of our success has to do with the company, the team, and the market that we go into. It's like sports: You put the wrong person on the wrong team in the wrong system, and they're not going to be as successful as they would have been otherwise. I just feel very fortunate.

The truth is, true product-market fit is so unwavering that any question of, “Do I have it or not?”—if you have it, you know.

Yeah, exactly. When you have it, when you have momentum and you have an advantage, press the advantage. If anything is working, disseminate that to the team. Press, press, press.

In terms of playbooks and things that work competitively, when we find something that works, we document it, share it, and press on that immediately. That changes all the time, and people react, and things change, but that's the kind of stuff that gets me out of bed in the morning.

Final one, but there are a lot of people who may be questioning whether they took the right step or made the right decision. You mentioned the interim move that you did, and with respect to companies, some decisions don't work out. I don't want to belabor anything like that. But any lessons or advice to someone who's thinking, “I don't know if I made the right step. I don't know if it was the right decision”? Any advice?

Mostly, when people come to me and ask that question, I say, “Are you hitting your numbers? Are you doing well in your role? Do you like your boss? Are you learning? Are you getting better? Is this serving you in a way where you're making an impact on the company and the company's making an impact on you to help you level up and get better?”

If the answer to all 3 of those things is yes, then typically I think you're in a good spot. If you've got 2 out of 3 or 1 out of 3, maybe it's time to think about what's next.

I walk every weekend with my mother—a marathon. I always talk about big decisions with her, and she gave me the best advice this weekend. I was talking about something specifically, whether I should start a fund. She said, “Move fast, but don't be in a hurry.”

Exactly. Exactly.

I thought it was brilliant. I think it's the same advice she gave me, which is that you don't want to sit and rot in a company, but you also don't want to jump too fast and too hastily.

Exactly. You have to be really thoughtful around it. Like I said, so much of it is around picking the right market and the right company. I think people over-index on title and under-index on growth. I'd rather take a role, maybe below the level you're at, at a high-growth company.

You did. You took the P&L of GTM, I think, or whatever, as the sole owner of your company.

Yes, yes. My company was the hottest tech company in Brooklyn. But yeah, bet on yourself. Have confidence in yourself and bet on growth. If you're going to come in and operate at a really high level within a high-growth environment, that's the best thing for your career, as opposed to having some ego around, “I'm X title. I want to stay that.”

I'd rather go somewhere where you can make a big impact in a growth framework.

Final, final one, I promise. Someone's great. They want a bigger salary than the rest of the people in that role. They're great. You and I both know they're great. Do you just suck it up and pay more? But what about what that does to everyone else who now wants that same thing?

You can't really do that. We have bands, and we have to have parity and fairness for a reason. That's one way to create a toxic culture: If people figure that stuff out, that leads to bad things in the long run.

Even though in the short term it might feel good because you get this person, you've got to go about it the right way, I think.

It's tough.

It's tough, yeah.

Right, my friend. You ready to rock and roll?

Let's do it.

Quick fire. What do you know now that you'd go back to yourself on day 1 and say, “You should know this”?

The degree to which the broader investor influence on our deals and the syndicate of influence around the opportunity matter, not just the opportunity itself.

All of that, I wish I had known sooner.

12. Why Investors Are as Important to Win as the Deals Themselves

It's interesting. It's almost like a land grab on investors as well.

Exactly. Like, if you look at our last fundraise, our CFO, David, described it as the investment syndicate. It sort of reminds me of Mission: Impossible.

I do. One of my friends is a GP at AirTree in Australia.

Yeah, yeah.

He pinged me about the war because they joined the round.

Exactly.

It's like a land grab in Australia.

Exactly. We want people who are leaning in and are going to really help.

Yeah, no, I totally get that. We mentioned Jude Law. What personality, individual, or brand would you most like to be in the next Legora ad?

Well, we have one coming up with Aaron Judge. That's going to be awesome.

That's pretty cool.

Yeah, very cool. I can tell you, I have a first grader in Brooklyn, and you go to drop-off at his elementary school, and the number of Aaron Judge jerseys is astronomical. So, very cool for him from a New York and U.S. perspective. We're really excited.

What one tool could you not live without?

I use Gemini all the time.

Wow, I wasn't expecting that.

Yeah.

What's it best for? I find it actually best for transcript analysis.

It's really good at that.

Yeah.

But it also has access to all the systems of work that we use. We use Gmail, Calendar, and Google Drive. So, from an agentic perspective, it has all the context and all of my stuff. It helps me with meeting prep; it helps me manage my calendar. It's very good at a lot of the simple productivity stuff, not to mention making funny pictures.

I have to say, I love Wispr Flow.

Yeah, Wispr Flow is awesome. Definitely.

So good.

Yeah, that's one of those viral products that everyone in Silicon Valley is talking about.

Great.

It's great.

It's really good.

The only awkward thing is in offices.

Exactly. Yeah, exactly.

In the middle of the office, I just talk to my computer and I just whisper.

Yeah, yeah. Well, I actually think that that's going to be one of the ways of working.

Our team has headsets, so they now look like customer support.

I was going to say, we've got a lot of headsets and a lot of AirPods going around. What was the best advice you've ever been given?

I had a mentor tell me that if you want to be a CRO, you need to be really well-rounded. I think mostly because, at the beginning of my career, I'd been really successful in a more transactional, mid-market sort of role, and then I moved into leadership very early in my 20s and was running a big team. I thought I was killing it, right? But I couldn't get a real VP job because I didn't have big-enterprise experience.

If you want to be a CRO, it's not just sales; it's customer success, partnerships, implementation, and onboarding. It's all these different things, and me taking a step back and doing different roles to give myself a broader set of experiences, I think it's been really, really beneficial.

Dude, I've absolutely loved this. Thank you so much for being so open and for putting up with my meandering. I got described the other day as the Louis Theroux of venture, which I didn't know whether to take as a compliment or not, but you've been amazing.

No, thanks so much, Harry. I really enjoyed it. Thanks for having me.