LB: The customers that are attracted to this are for reasons X, Y, or Z, but also the people that you bring along to get interested in solving legal technical problems or engineering problems or UX problems in the legal space, all the people that you need to bring together to do the magic that serves the customer community.
JB: I still feel like we’re in the hacker phase of legal technology and community. An analogy someone used for me back when we were starting Ironclad was in the home-brew computer club days of legal technology. It might not be perfect, but there are energy and enthusiasm among the early adopters to create something that I think is magical. And one of the blessings of that is that as a founder, I think you get many true believers who bought in, who are convinced. There’s no hype cycle around it. So you find a few people who think it’s cool and get excited about it and the vision. I’m interested because I feel we’re at an inflection point. One of the things I’ve talked to the team about is the need to be careful about who we’re hiring because there is a bit of a hype cycle now, and we don’t want the people chasing whatever the cool area of technology is. In some ways, the quality and caliber of incoming recruits these days are higher than ever, but it’s harder to distinguish the true believers and community members.
LB: What has caused this to come to the surface of your consciousness, enough for you to articulate that?
JB: It’s probably more of a feeling. I’m a very intuitive person. In some ways, it’s the success that our industry is experiencing, certainly not for the first time, but with newly re-invigorated business results. It’s pretty hard to ignore business results, and I think investors in Silicon Valley are starting to see this is a great business, and there’s a lot of ways that this business can continue to develop. Some of that’s within what I would consider the core of the legal industry and legal technology, and some of it’s a little bit adjacent—for example, DocuSign. I would call them a legal tech company with, $40 plus billion market cap. That starts to get people pretty excited about what’s possible here, and I don’t think anyone, including DocuSign, would say that they’ve solved the contracting problem. So, it’s like a bit of a gold rush to this massive market opportunity in some ways.
LB: Yeah, I think that’s true. Talk a bit about the approach you’ve taken moving the business from start-up to emerging stage. And whether or not that’s the same approach you’ve taken to funding, to building out a management team. Would you share, Jason, how you went from, “This is an interesting idea with some early-stage adoption” to, “Wow, I got a real business here that I’m building.”
JB: That breaks down into two stages. One is searching for a product-market fit. To cover that one quickly: we had a viewpoint that CLM has traditionally been a database-driven industry. If you looked at the top players ten years ago, it’s databases. Every corporate function needs databases, a CLM database for contracts. The problem is you have to get stuff in the database. Only big companies can afford the people that put things in a database. We had this viewpoint; how could we allow everyone to have the benefits of contract management? Whether you’re a surf shop or selling coffees, every company should know what’s in your business contracts, and you should have those at your fingertips. You probably don’t have time to hire a contracts manager if you’re a surf shop. How can we let every company in the world experience the benefits of what contract management should be? We realized, taking a broad look at the problem, the problem is much bigger than simply, “how do you find your contracts.” It’s, “how do you make contracts?”
Nobody likes making contracts. Everyone views them as a blocker. Is it possible to solve both of those problems with one product? And we looked at that, and we said, “we can solve the database piece. The unproven part is, can you link up contracts with the database and have that be something people enjoy using, and even lawyers would want to switch their workflow?” We spent about two years figuring out whether that was possible with a wonderful group of customers and emerged with a pretty exciting business growing organically after that. And so we felt like even though we didn’t have the full products, we had a solid viewpoint that we could achieve product-market fit, and we knew how that looked. So at that point, we shifted into, “Okay, let’s build a business, and let’s think about the path to becoming a large independent company over the next decade.” My co-founder and I never thought we would be start-up founders, and we’re not interested in being start-up founders beyond the Ironclad problem.
We just want to work on the Ironclad problem. So we set out to build a very long-term business. One of our principles for doing that was that we always wanted to act and behave like a much bigger, much more mature company than we were. Even the name Ironclad evokes a large company name, and we’ve always tried to act with that level of maturity and long-term decision-making. I would say that underlying ethos has been part of the company from the moment we realized it’s possible to build a big business here, and we felt like we’d identified that product-market fit.
LB: When you move past that phase to okay now, we have to take it by its tail. I think this is your first business. How did you figure out the steps you needed to take to ride this opportunity or release its potential?
JB: Well, I think in some ways, it is my first business and my co-founder’s first business, which was an advantage because it was very clear. We understand the product. My co-founder is an incredible software engineering product builder, and I just love the problem space of business contracts and legal teams and that kind of problem area. So we love the problem, and we know we want to work on it for a while. Let’s take advantage of where we are in the world, which is the center of Silicon Valley, and let’s recruit and identify software talent who has done this before and from whom we can learn. We started building our executive team when we were 17 people. I’ll put our team up against any company at our stage, and I think our investors will back up the quality. We’re still building the executive team, and it’s full of not necessarily people who have come from the legal industry, although there are some. It’s people who have built significant and lasting software companies. We take that attitude of learning and wanting to level up our game and our knowledge level since we haven’t done this before.
LB: Bringing people together from the software world, adding in a mix of people with the legal world, how do you get everyone to be as engaged, excited, and effective in collaboration around this? In that first two years, you asked a lot of questions. The problem caused you to ask a lot of questions, and it seems to me from the way you tell the story that you cycled through a lot of questions until you ended up with some high-quality questions that informed this viewpoint that you have. I would go so far as to say, if you’re a lawyer or a legal professional that’s listening and thinking, “Wow, I’d like to be a founder or a CEO of a legal tech business,” I would say, “Please listen to what Jason said there about spending real quality time.”
There is no way to short circuit the time with customers, honing in on the highest quality questions that inform a unique viewpoint. That will give you almost an unfair advantage, a head-start, where you start makes a big difference. I would argue that where Ironclad has started, the questions you’ve asked, and the viewpoint that you’ve developed are things that businesses are going through. I’m sure there’s a lot of aha conversations going on. “Aha, I never thought about thinking of contracts in that way. I never thought about contract technology in that way.”
You bring all these executives together, and I know what it’s like to work with Sand Hill Road, the Silicon Valley venture community. They’re very connected. They bring together lots of people. How do you get all these people working in other areas, passionate and aligned around a problem like this?