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Talent wins games, but teamwork wins championships. Welcome to eight players. But guess what? We'll tell you how to target, hire, retain and train performance for the next phase of the company. Once you find that initial product market fit really is about scale. And one of the best ways to get scale is to bring in experienced contests. So the faster you do that, the better in some ways. As long as you can maintain a high quality bar there.


So we started the executive process pretty early and it's only recently reached like a fully built out executive where we've got experienced folks at the helm of every key function in the company.


I am rubbing shoulders with you at higher suites and we are sourcing automation software that helps manage the tech companies. Hire the best talent at me and follow me now on the team. You want to keep an eye on this? Perfect. Cool.


So today we're hosting Jason Demnig, who is the CEO of Iron Clad in less than six years to grow the company to the company of 160 employees, raised a total 84 million dollars. And today, I'll tell us more about how to build a team of eight players as a CEO. And how do you scale that?


Cool. So welcome, Jason. Can you tell us just a bit more about iron clad as we start?


Yeah, of course. Robin, thanks for hosting me. Really excited to be here. And I love the topic because it's something we think a lot about at iron clad. Real Quick Iron Clad is a digital contracting platform. So what that means is every element of a business contract we help our customers with. So we help our customers make business contracts a lot faster, a lot more efficiently and with a lot more legal compliance than you can without iCloud.


And we also help companies take advantage of the information in those contracts. So you think about payment terms or expiration dates or logo usage rights, all sorts of these operational pieces of data for companies are trapped within these long form text documents. And we actually make them data, we make them computer code and we make them be able to talk with all of the other pieces of software that companies use. So if you're a salesperson and you want to make sure you never miss an expiration date or you want to always know how many seats you sold, that information is going to be live linked in Salesforce for you at your fingertips if your company is so making and managing contracts for companies.


And what does the team look like today? Can you tell us more about that? And also, the Sunline twisted if you have a data science team to do that, processing part of detecting the payment terms, et cetera.


Yeah. So team looks like I mean, we've got kind of the functional business areas of ironclad. Our customer success is actually our largest team at the company. We have a chief customer officer came from Salesforce. We can talk about some of these exact recruiting milestones at some point, but we've got a customer service customer success team. We've got a pretty big sales team. We've got, of course, a big product engineering and design team. And then ops and legal for us is pretty important as well.


Yeah, we've got a pretty built out and well rounded functions that ironclad headed by pretty experienced execs.


And how involved are you into hiring today yourself?


I'm incredibly involved. I'm incredibly involved. And I think it's one of the jobs of a CEO that never goes away. I'm involved in a little bit different way than I used to be. And I'd say it's more at the executive level where a lot of my time gets spent. But I do still try to take quality control and quality, check every hire that we make. I'm not in every interview process anymore, but I do love meeting every level at the company.


I think that bar is ultimately my responsibility.


OK, so today's more quality control and hiring the executive team. Exactly. And how how did you see that evolved when the company grew? Did you see certain milestones? Will you completely change roles? For instance, when did you start interviewing with everybody that joined the company? Yeah, so we've done this a little bit differently than than some other companies in that we've we front loaded some of our executive hiring, which I think at the time was pretty controversial.


So, I mean, we brought in a CEO and a VP of engineering when we were under twenty people. And at the time, like, I'm not even sure I was convinced of that. But one of our investors, Steve Lofland, who's just a fantastic investor, he started really the IQ was there to look to Salesforce for I don't remember the exact number, but hundreds of billions of dollars and had built a great culture there. So we really saw him out for our series A Round and talking to him.


One of the things I realized, I think a little bit early is the next phase of the company. Once you find that initial product market fit really is about scale and one of the best ways you can get. Goal is to bring in experienced x x, so the faster you do that, the better in some ways, as long as you can maintain a high quality bar there. So we started the executive process pretty early, and it's only recently that we reached like a fully built out executive where we've got experienced folks at the helm of every key function in the company.


And that that starting process actually looked like Steve introducing us to some folks in his network. We're able to hire some of those folks and then that it was almost a domino effect of when we met other experienced. Exactly. Might not have joined a 50 person company, for instance. They were like, oh, actually, I see some other quality execs in maybe I'll give this a little bit more of a shot than I was thinking. So part of the reason I think it paid off to start that process early, because it really is a tremendous time investment to bring on some of the really senior folks.


So you did start to hire a team of 20 people in the company, but you waited until you were sure you found product market fit, right? Exactly.


Yeah, that's both for the reason of like, yeah, these are expensive and kind of difficult players to make. But also, I don't think unless you've got a pre-existing relationship or you're able to pull off some real coup, I don't think the real experienced or senior techs will join a company that has a product fit because their skill set and their problems is working with large groups of people. And it was a challenge to sell that at 20 people because you have to basically sell the dream and say, look, you're going to be working at the scale you want to be working at at some point.


But I think prior to product partnership would be a tougher sell that I'm capable of at least.


OK, and when did you start hiring a recruiting team? It's what stage of the company? Yeah, that's a great question. So that was shortly after the series as well. And that one, I think perhaps even more clearly, the product market fit. I was talking a little bit about this transition from stage one of the company basically find product market fit and do whatever you have to do their stage to take that product market fit and build the right business model on the right team to service a large go to market strategy around it.


And so once you got confident or once we got confident around the product market fit, it made a lot of sense to hire a recruiting team. I remember that at the time, still feeling like it was very early. And while this is kind of scary to bring a recruiting team, but looking back, I'm so glad we did it at that time.


How did you build the recruiting team? Did you hire one person or did you hire several people in the same time? Yeah, I mean, similar to the we we hired one really key recruiter who just did everything and is a senior recruiter who is the type of person who now manages a pretty significant team at Ironclad but was kind of hungry enough to come in and say, I'm going to do literally everything from booking meetings to sourcing and outbound ing to running candidate debriefs and just kind of had the drive and hunger to actually do that at that stage and now runs the team.


Hobie's the team today believe the recruiting team's five people, five people.


So that's about when one employee per twenty five people in the team. Right. One to twenty four. Yeah. OK, cool. And so you are your executive team and. Oh did you do that then.


Mostly referral first just said from your investors, did you work with search firms, did you work with a software that you used. Any specific deep's that you had.


Yes, our first three executives, we did not work with a search firm and I think it was because we were hiring them a little bit early. I'm not sure we would have been able to get just from a regular networks the interest that we would need to fill the role. And so two of those came from network where there was a somebody in our extended team had worked with them. And in the case of our first two decks, that intro actually came from Steve, our board member, Excel partner, which tremendous value add from an investor.


I think it's one of the biggest value outs that an investor can bring. And then the other one actually came from our advisor network. So I think Advisor Network can be a really great way to go earlier on that you'd otherwise have a hard time recruiting because through the advisor relationship, you can get them a lot higher fidelity information and you can start to get interest around the company in a way that that's just difficult to do if you're you're taking a 30 minute and coffee around an actual hire.


So in that case, I had actually just identified there's probably two or three people in the world that are really great at our space, which is kind of a weird space. It's like a little bit of legal space in that a lot of our buyers are in the legal function within their companies. But it's also very. Classic SAS motion in that we're selling software that helps companies do business, and it's really breaking a new market because it is selling to a new buyer within the organization, but it is selling a business type of solution that has analogous pieces of software and other functions.


And so I was looking for someone who had a legal background in our VP of sales, was a lawyer, is just like if you look up his profile, the perfect person to join and lead our initial scale of going to market. And he has a legal background. He has a software background. He's worked at companies like DocuSign. So just kind of going out and proactively identifying those folks and getting to know them. Maybe one or 10 of them actually works out as a hire, but you certainly get a lot of value from having those conversations as well.


So what did you do? Did you reach out to them, reach out to them and really genuinely was just seeking advice at first. And I would love to know what you're thinking about this. Like, how should I think about our first a higher and throughout the process of just kind of hearing about our business get built and seeing the types of questions that we were running into? He got more interested. It was funny. I remember the first meeting with him, him saying, just so you know, I'm never going to join a series, a type startup.


So I hope that's not why you're bringing me on as an adviser. However, I'm really interested in helping because it's kind of a fun stage and I'm happy to provide some advice, but eventually got him OK.


That's good advice as well. And my other question would be, you consider the top performers or players or top performers for your team. You mentioned specific background that was needed, legal software, etc. all.


Do you find common traits among all top performers across different roles, different teams, different companies?


Yeah. So there's definitely a baseline common trait. And I think to be a top performer, I've never seen a top performer that doesn't have a growth mindset because you're just going to encounter so many different problems at this stage. You have to be. And I think that mindset often carries with curiosity. People that are top performers at our club that I've run across my career are curious. And if they face a setback or if they face a problem that seems difficult, a lot of people might back away from that problem.


But the players will get curious about why, you know, the solution that they try isn't working or what, two or three layers deeper within that problem. And so that curiosity and growth mindset and excitement around learning, I've never encountered a player that doesn't have it beyond some of that just fundamental, almost personality traits, though I think there's almost no way to systematically identify. And if I look at the players across cross ironclad, I mean, just to take our legal engineering team, for instance, which is works with our customers to kind of solve our customers the most difficult problems.


You've got folks on there that have like backgrounds that are more typically obvious, a player backgrounds where they worked at McKinsey for two years. Then they went to Yale Law School and then they worked at a top law firm for a few years. And as you can imagine, that person is exceptionally smart and driven and they also have a growth mindset. So a player. But we also have players that, like one of our players, started doing data entry for us for minimum wage and was so good and so productive and had such a good attitude at the data entry.


We look for another job and she crushed that job and we gave her another job and she crushed that job. And she was like the cousin of a wiki founder that was temporarily in the Bay Area doing, I think, a nanny job. And we eventually convert her into a full time employee. She's like, run different teams that I had started at the company when she was nineteen, doesn't have a college degree and is absolutely on the same team as that kind of McKinsey player.


And they respect each other the same level they perform at the same level. So just looking at those resumes, you'd never be able to tell a similarity between them. But the performance is absolutely there.


And did you detect that from the person? Did you detect that in the interview process, or was it only when she was into the data entry role that you discovered?


That's a great kind of thread to pick on here, because the way we were able to detect that with her was not in any interview. The interview process there was basically like the work. And we really did use this tool in the early days, which was any possible time we could get somebody doing work, whether it was like a week long consulting agreement, whether it was just even a few hours project. First of all, we always paid them for the work, but.


Second of all, it gave you such higher fidelity than an interview and what it was like to work with this person, like how did they ask questions? How did they go about solving problems that weren't obvious? Did they sit there and Google for six hours before they would ask anyone or did they ask too many questions and should have done a little bit more independent research? So some of these, just like working style things, are pretty easy to flush out in a pretty small project.


And then giving folks a shot of money to improve themselves often produces surprising results.


And did you manage to embed that into your hiring process? Because I think it's easy to hire someone to give them some work when you are 20, 30 people in the team, because you could keep an eye on that and you need help anyway. But when you need to scale fast, then you need to have people going through regular interview processes. Did you find a way to give that actual work component later in the hiring process?


Not for every role and not all the time. It's still a strategy that we will employ where it works out. But also I think it does pair better with the types of people that you're interested in the really early stage job like you got to kind of be in. I mean, this is the most affectionate way possible because I consider myself one. But you've got to be kind of a weirdo to work at an early stage, free product market fit company, like it's not a normal job.


And so I think there's a higher tendency of candidates who are interested in a very early stage product or a company to be able to do something like take a week and actually go sit in a converted apartment and tack on something. Whereas just because we're hiring more people now and we're at a different stage, I think the candidates we look at now are often in a competitive process and looking running interviews with two or three similarly profiled companies. And there's just not the capacity to do a week long project.




That's the second time you mentioned that there is a real gap between free product market seats and product markets. It's in the hiring. Do you see specific advice that you like to give to pre product markets? It's cofounders that wouldn't apply those product market fit?


Yeah, I think in some ways you can you should even devote more time like we do about a ton of time today to hiring top talent. But if you think about the impact that early employees have on your company, it's just enormous. Like there are still almost like personality traits of early iron clad employees that are prevalent and dominant in our culture that probably wouldn't be there if not for that person. So every hire you make between one and ten is so impactful and the echoes of that hire will be felt for years at the company that you cannot spend enough time on it.


And I cannot overstress how important that is. Like I said, its hiring is always important, but those those first 10 hires basically determine the trajectory of your company and how successful you'll be. So invest everything you can in that.


And you think that the the co-founders should do this recruiting work themselves. Do you think they should hire someone? Do you think they should hire the firm? What do you think? And I'm still talking to yeah.


I mean, with the caveat of this is just our journey and I'm spouting advice that's worked for us. So no one should take this as gospel. But having said that, I can't imagine a world in which founders shouldn't do one through 10 themselves just because it is so personal, like the product you're building. It should be personal to you. You should really care about it. And you should want to have a style to how you're building that product.


And only you can really understand that style, the culture you're building, like you should want to build a culture that's unique to your company and that has things that you uniquely love. So you're the best assessor of what that style and what that culture is. So because it does involve so much taste, so to speak, I don't think you can outsource that taste to someone else. And what you end up getting is the company that someone else thinks you should build, which is going to be hard to actually scale and hard to maintain.


OK, and know.


Fast forward to twenty twenty. He told me before that you were working at Lehman Brothers just before the financial crisis, is that right? Yeah. Cool and not so cool but.


And how has your school actually that was how, how was that experience influenced you leading the company today right in the middle of the pandemic and the covid crisis in the US? I think there's a couple of themes.


And the reason I say it was cool is it was a fantastic experience early in my career. So for one, Lehman did have, I think, a unique and special culture among the investment banks. There was almost like a chip on our shoulder and there was a lot of talk of we wanted to go to Goldman Sachs as a. The world and and that kind of thing, and we came into work every day hungry and with a lot of team energy, so I liked seeing that kind of culture.


It was a great education for me as well. It was very challenging. I never had a job that required that level of performance. And I think and some commitment to excellence that might have been hard to find elsewhere, even though even though as a CEO. Yeah, even yeah. Even now, like you just I remember I remember like having I was writing a 30 page report or like page or something and I had size 11 font on probably like page 12 of this report and the rest of the thing was size 12.


And I just never had had a job that paid attention to that level of detail before. And it stuck with me ever since. Like that excellence in everything you do. And maybe that was just the little team I was on. But we still care about that stuff at Ironclad today. And you'll see people pointing out size 11 versus size 12 across the company just because we care, we want to get it right. But the crisis itself was also pretty interesting.


And again, I think I was fortunate to be early in my career because it truly was sad to see folks that had been at Lehman for 20 years have their life savings wiped out, which was then Lehman stock. For me, it was kind of like I'm going to go back to law school now. That's a good time to do that. The big take away that I do think is relevant every day is the founder is I was sort of in awe of the competency and smartness of the people that I worked with.


And these people had better educations than I did. They were just sharper than I was there. I really looked up to them and I remember questioning. So my first day on the mortgage backed securities trading floor, I read an entire prospectus because that's just how I like to work. And I remember like going writing down like ten different questions about the actual securitization of mortgage backed securities and digging into why this is working. And this was working. And I remember my bosses at that time being like, hey, dude, never do that again.


Like, we just sell that stuff. And trust me, it's fine. Like, you don't need to worry about those level of details. Like, we got this and this guy had like two degrees from Harvard. And I just was like, OK, he's a lot smarter than I am, so I'm not going to worry about that. And I'm kind of embarrassed that I actually went and did that level of no.


I think that the thing that I mean, really didn't. So the lesson I took away from this was like large groups of very smart people can be very wrong. So they genuinely believed and I genuinely believe because I trusted them, that this was all going to work out and the way things were structured was OK. So just like viscerally witnessing that failure of many smart people being very wrong and the kind of groupthink involved in that, it's hard to shake that lesson.


I think it does stay with me pretty much every day. I'm fine. And it's helped provide conviction during difficult moments of the company like early stage. What we're working on our flight is very ambitious. We're trying to build a system and we have built a system now almost six years later, that any type of business contract can go through. So we've got our customer, L'Oreal. They have one hundred fifty brands and each of those brands are sending out influencer agreements thousands per year.


You can check out a cool video on our website about this, but that type of contract works on our part. And we've got hundreds of tech companies doing everything from sales agreements to carrier agreements to shipping agreements to photography release agreements. We've got professional sports teams. We've got hundreds of year old publishers. We've got companies from just about every industry you could imagine doing business contracts on unamplified. And the advice we received early was just focus on one contract type.


That's a lot easier of a problem. And this advice was coming from very smart people. But my co-founder had a real conviction that in order to accomplish the mission that we want to accomplish, we're going to have to, from the very start, build a system that can take on any type of contract. And that's a much harder problem. But if you solve it, it's much more worthwhile and much more valuable, and it's just what we wanted to build.


So being at Lehman in some ways helped me have that conviction in a way that if I wasn't there, I think very, very large groups of very smart people telling me not to do something would have been more persuasive to me. And I think that kind of like sticking to your guns and sticking to the vision as a founder is really important and also really hard to do at the early stage. When there is no right answer, you just have to find your way yourself.


Do you think that applies to when building the team? Because there's still a lot of biases, prejudices in hiring, obviously a lot of wrong decisions and very good things can be hidden and everybody would agree. Not the players, but they could end up being one like the person you mentioned before. How would you address that in hiring?


I think it's one of the biggest burdens of the CEO to it's like your and the founding team generally, like you, me and my co-founder are the bearers of that ultimate hiring decision. And sometimes you have to ask for the team's trust. Like when we brought in our first executive, we had a pretty significant amount of team members that are like, why are you guys doing this? We don't need a freaking CEO. We're less than 20 people. Like, why are you creating a layer, a completely unnecessary layer of the company?


We don't get it. And I said, you're going to have to trust me on this one. Like, I know it's not obvious, but this is part of my job is is charting the next course for us. And I really believe this is the best for everyone and made the hire obviously was empathetic and understanding of all of those comments, but had a firm belief that it was the right hire. And then six months later, pretty much everyone, well, everyone came back and was like, oh, my God, thank you so much for making that hire.


That was amazing. We love working with this person. I can't imagine what it would be like if we didn't make this hire. So sometimes you do have to have that vision and the conviction around the hires and like ask for the trust of the team as well.


This one is a very good example of what most people would say is a bad idea. But you ended up doing it and there is no right recipe to building the team. That's right. You sometimes have to do the very architecture that will suit your own company. That's for very good advice. My last question for today would be what's the number one advice that you'd give to your 10 years younger self or six years, the beginning of a younger self?


Yeah, my 10 year self. So my 10 year self would have been going back to law school after having a career on Wall Street. And honestly, it was a little bit of a humbling experience. So I went from a pretty great job, like making a pretty good amount of money to like making no money, being a student. And then also my career path being almost kind of reset to a first year associate, which was my job out of law school.


And as someone who is a little older than other first year associates and it was a little nerve racking. So my advice to myself ten years ago would be like, it's going to be OK. Like, you know, you're doing the right thing and don't worry. My advice to myself six years ago would be to kind of like what you just said. It is there is no right way to do this and just be true to yourself and ourselves as an early founding team.


Thanks a lot, Jason.


That was great. Very actionable advice, like the part about the hiring your exec team soon. I hope a lot of people have the inspiration that. So there was great having you and and talk to you soon then. Yeah.


Thanks, Robin. This is such a great topic for a podcast. So something near and dear to my heart. And I really appreciate it. Thanks. Thanks for listing the podcast. Till the end. If you're still with us, it's probably that you enjoy the players. Eight players is brought to you by myself and our suites. We are building a sourcing automation software and we already have 900 companies. Hire the best science to know more about us.


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