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?

JB: That’s a great question. And I think it comes down to how you hire and what you look for in the hiring, especially at the executive level. The company is changing so fast. One of the things I’ve learned to look for is curiosity and a growth mindset. We are solving and encountering new problems every day. It’s amazing, the attitude difference and the growth trajectory, when maybe the only variable of difference between two people is the level of curiosity. People who get excited when they encounter a new type of problem and take learning when they solve it for the first time can bring that learning the second time they solve something similar to a higher success rate. It’s amazing to me. Given some basic intelligence and domain knowledge, I will look for curiosity and a positive attitude as the differentiator in success among different candidate profiles.

LB: It’s interesting you talk about this curiosity. One of the things that’s pretty clear to me when I work with people when our ideas meet the real world of serving customers is that there are two sets of responses. There’s one group of people who see customers as problems. Customers are demanding, they are never satisfied, and customers are problems. The other pool of people sees customers as this fantastic, never-ending source of interesting problems to solve. I think that goes to your curiosity mindset. Even with my gray hair, I continue to struggle with solving the question of, how do I make sure we hire people who see customers as the source of curious and interesting problems? How do you determine whether or not someone is curious?

JB: That is a really good question. One way you can do it is by references. If there’s one thing I’ve learned, it’s that.  Suppose I’ve got an hour to dedicate to learning about someone. In that case, I will use it talking to somebody who has worked with them and is in a psychological place where they can be open about their experiences and be tremendously valuable. I always like to start a little bit earlier than is traditional in going over someone’s background. I like to dig back. What was your first job? What was your first experience with work? And see if there have been learnings, what is their attitude toward menial tasks. A couple of anecdotes that stick out from people at Ironclad. One of our early employees told me his first job was shoveling manure, and his attitude about it was that he learned all these things, and it was on this farm, and he had all these observations.

Someone else worked in their parent’s restaurant growing up and figured out a new way to improve the kitchen process, a new system of answering the phone. I look for the little improvements that people have made. The world around us is amenable to improvements. They don’t need to be dramatic. Marginal improvements along the way, or just finding that slightly better way of doing something, seems to be a pretty good predictor.

LB: As you look out over the next couple of years, what are the obstacles you think that the business or the executive team, or perhaps you personally, will need to overcome?

JB: I talked to one of my mentors and advisors the other day, and I asked him a similar question of how I should think about the next few years.  He conjectured that there would be fewer fires, but they’ll burn hotter as you continue to get bigger and bigger. It does make sense. If I rewind to earlier in the company, I remember very distinctly that we were raising our Series A, and we were 15 people or something, and we didn’t have anyone that was sending out invoices. I did my day, and then I remember making a Series A pitch-deck and then sending out some more emails, and then it was 2:00 AM. And I had to send out all of our invoices and send them from our invoices address, so they didn’t realize the CEO was invoicing them. Today the company is extremely well-capitalized. We have teams doing every function you could imagine; there are no missing gaps. We have experienced executives at the helm of everything. I can just see that continuing to play out and there being fewer fires, but they’re burning hotter. As long as we remain focused on the customer and continue to be the most curious, the most passionate, and most diligent people interested in that problem, we cannot fail to be successful.

LB: That, in an ordinary year, seems like an easy-to-accept answer. In this year, being a leader, how have you kept everyone focused on the mission? Has this year had an impact on the fires you have had to put out?

JB: It’s certainly been a lot of change, particularly for Ironclad. We were a very in-person culture before the pandemic. In some ways, I think it was easier to transition to remote when everyone went from being in person to being remote in one day; there was no half stage there. It’s certainly been full of change. I’m very grateful. It’s been a great year for us. And I’m proud of the team for how they’ve adapted to rapidly changing circumstances. It hasn’t been without challenges; it’s been a year in which we’ve thrived as a company. The team gets put to the test in a moment like this, and we have adapted a ton. One thing that’s interesting for a company with a lot of legal DNA is we’ve moved towards a writing culture. Even on the executive team, we spent an hour-and-a-half every Monday in a conference room together, and there wasn’t a lot of prep for it. It was like we just knew we would solve the problems ahead of us if we got in that room. And remote, you just have a lot less context. We each write a briefing by Friday afternoon, and we send those around. And it’s a cool innovation that I think we’ll take with us into the next stage. I think it’s a big competitive advantage to have that clarity and way of communicating available to us.

LB: We’ve talked about techniques and tools and how you’ve developed into a business leader. Are there any books or writings that you’ve read that have informed your executive development?

JB: I’ll give you two that my team would probably say because I talk about them all the time. One is The Score Takes Care of Itself by Bill Walsh. Bill Walsh took over the 49ers when they were terrible, and it’s about how he turned around the 49ers and the systems and processes he put in place there. The high-level thing I take a lot of ownership in is that a leader has to set forth and be accountable for a standard of excellence. And so, he put forth a standard of excellence. What’s interesting is where he started applying that standard of excellence. So it wasn’t, “We’re gonna win five games this year, eight games this year, and then 11 games.” He went in and was like, “We’re gonna answer the phones this way, and we’re gonna pick up every single piece of trash after practice.” And it is a non-intuitive way to start building a culture of greatness, with just tiny things. The thing I love about that is you can do it in a day. You can answer the phones better after one day, you can have a clean locker room after one practice, and you can build off the momentum towards those things to achieve a culture of winning and a culture of greatness that can become pretty lasting.  I love that book, and it’s always inspired me when I go back to it. The more off-the-wall one is called Honeybee Democracy, and it’s basically about how bees make decisions.

Bees are good at identifying the optimal location for their next nest.  One of the things this book details is how they do that, and it’s through group decision-making. The core mechanic that they use is there are lots of people doing different things, and they very quickly come back and report what they found and their take on the situation. The bees will go out and investigate every possible place for a nest, and they’ll come back, and they’ll dance. And the length of the dance and the vibration frequency communicate how good a fit they feel that nest is. There are some mysteriously objective criteria that they’re using. That’s quite fascinating, but I love the concept that if you had an organized hierarchical way of finding a nest, you would never get to that. But you’ve just got bees out there, basically talking to customers and bringing back what they’ve found from that customer. Once the swarm decides to move, everyone goes. It’s not like some bees go to this one, and some bees go to this one. The vast majority of bees have never gone to the next nest location, but there’s this critical moment where everyone goes. So I love that everyone’s reporting information back, but then we all go to the same place type of thinking, and I aspire to build a company that adheres to that.

LB: That is fantastic. My last question. I’d like you to finish a sentence for me, please. And the sentence that I like to ask is, “Leadership in tough times requires…”

JB: The first thing that came to mind was care for people. So I think leadership in tough times requires care for people. That manifests in a couple of different ways. I think of it as, if you’ve done things correctly, there’s not a lot of reacting to do in terms of decisions. You are trusting the team that you have put in place to execute when that crisis hits. I think of my job as caring for the team. And so I’m checking in with every exec. What do you need from me? Are you getting sleep? Are you able to make decisions? Do you have the right resources? If not, I’ll track those down. Care and understanding for people.

LB: Jason, this has been a fascinating conversation. Thank you for spending this time with me, talking about leadership and law.

JB: Thanks for having me; this is a great series, and I hope to continue the discussion in the future.

About the Author(s)

The host of this interview is Elevate’s Chairman and CEO, Liam Brown, talking with Jason Boehmig, the Ironclad CEO.