Why Being A Great Technologist May Not Make You A Great CEO

Uh, great. How many people in the room know Wayne Gretzky? >> Most people. Wayne Gretzky. >> What's the advance button? Hit that. >> There you go. Wayne Gretzky is generally thought to be the greatest hockey player ever. Um, I think he's the greatest team sports athlete ever. But if you notice something about what's on the slide, after his unbelievable hockey career, Wayne Gretzky became a coach. His coaching record was not so good. Most people forget that actually after coach, he became part owner of team and he became a general manager and he wasn't that great at that either. And sometimes you got to think about why. Sounds good. >> There's another a different example that I can provide

also coming from sports, Mike Shasheesky. How many people heard of Mike Shasheesky? Uh, you've probably never heard of him as an athlete because he really wasn't a very good one, but you've heard of him as a coach because he's generally thought to be the best college football, sorry, college basketball coach ever, winning five national championships, coaching teams to gold medals, etc. If you think about the title of this talk, which hopefully didn't offend, but when we talk about why being a great technologist may, and I'll emphasize may not make you a great CEO, it's because they're completely different jobs. They require different skills. They require different experience. They require different demeanor. And I think it's

important for anybody who's a technologist thinking about becoming a CEO to understand that difference. and a make sure you want to do it and b prepare yourself to be successful. So my job today is to talk a little bit about that and expl and and talk about some of the differences and what my experience is as a CEO and uh what you might think about getting from point A to point B. Um just as a quick introduction, I'm Jason Kaplan. I'm the CEO of a company called Sixmap. We're upstairs. The day is almost over, but we we'd love to talk to you technologists about what we do. We provide external visibility to enterprise networks so that we can give

you an attacker's view of what your vulnerabilities or what's exploitable. We do it differently. There's a lot of companies that do it and again we'd be happy to talk to you about it. Um but my journey actually started in sales. So I didn't have to uh traverse the journey if you all are technologists that you do. Um I was an inside sales rep calling the phones a long time ago in technology. And over the last 25 years I've learned a lot about technology. I've been a co-founder, CEO. I've taken over for technology founders as CEO. Um, and I'm now CEO for the third time. I've sold a business and now I'm CEO for the third time.

Um, this is something that when I was preparing for the talk, I was thinking about how often do you think a business or a sales or a marketing oriented entrepreneur has a technology idea and says, "Hey, I think I can go build it." And tries to play both roles. And the answer I think is not very frequently because we at least I know I could never build that myself. the opposite question of how often does a technologist say I'll be the CEO and goes out maybe raises some money maybe not but says I I can do that and then faces some challenges along the way and I and I think probably the scenario that you find more often is technologists

think they can be CEOs and and again if you talk to VCs and you talk to other people um that journey is not always so easy and I think the question is why so this is you know again we'll go through this over a course of a couple slides, but it really starts with the differences in what the jobs are and what the the leadup into the role is. So, as a as a technologist, and look, I'm not one, but I've worked with a lot over the years. Often, what's most interesting is solving hard problems, is building cool things, is creating innovation, right? All of that sounds pretty interesting, I think, to most techn most technologists don't get in it

to, you know, sort of move a rock from point A to point B. They do it to build something new and exciting. as a CEO like my job kind of doesn't have anything to do with that. My job is about how do we create something that will solve a problem that people will pay for today. That that's the job and as a business like that's what you have to do. Whether you create something innovative or not is sort of irrelevant. Your product obviously it matters but is sort of irrelevant. What matters is will people pay for it today? And so the perspective of a CEO is not necessarily what are we building that's most innovative or interesting or

challenging. It's what is the customer's pain and am I building something that's going to solve that pain today and can they actually implement and use it because lots of technologies get built that are very difficult to implement or to use in which case even if you're solving a hard problem you fail. So what the outlook on your business is and what you the sort of the problem you have to solve as a as a great technologist versus the problem you have to solve as a CEO or among the problems you have to solve as a CEO are very very different. There's another very practical reality which is like how do you spend your time? You know what do you like to do?

And um what sometimes frankly even surprises me like at the end of the day I'll look back at my calendar and I'll see you know little blocks of colors all day from whatever it is 8 to 6 and it's all different. But you know as I was thinking about how I spend my time and as I've talked to other business leaders about how they spend their time um very little of it is actually spent on technology or solving technical problems. Um, this is representative. This is, you know, basically nothing's the same, right? Week after week, but probably something like 40% of my time is spent calling customers, visiting customers, traveling, thinking about marketing, thinking about this event,

preparing presentations, doing things that are all about selling and generating revenue. About 30% of my time, and this may be surprising, is just dealing with people. Um, when you start to hire, first, hiring takes a lot of time. um how do you get people onto your team that you want? Uh how do you as a lead technologist convince a CFO or head of product to join you? Um so hiring takes a long time, firing takes time, ma, you know, there's lots of complexity in life that you have to think about how do you set a policy and communicate it to the team. So people management takes a lot of time and then there's stuff like

admin, legal, finance, etc. Um, I was talking with uh one of our somebody who's a partner in one of our VC firms earlier this week. He asked me to speak to a a CEO of a new investment they made and this is a 30-year-old CEO who had already started and sold a business. Um, but Andy asked me to speak to him and so we were talking and and the conversation went really really well. And afterwards I called Andy and I said, "Hey, I thought we had a great conversation with uh Eric was his name." And um and Andy said uh you know I'm really excited about him but he comes from like a sales background and my concern is he's not

going to want to do the boring stuff you have to do as a CEO and that speak that's about getting the legal documents right getting insurance you know picking a place to have your office all of these things matter. So again, when you think about how do you like to spend your time, be prepared to spend your time doing things you don't like doing because you have to. Somebody's got to get it done. And especially if you're starting a company, there's nobody but you to get it done. This whole chart is irrelevant when you start uh raising money. When you have to start raising money, you will end up spending somewhere between uh 50 to 80% of your time raising money.

Period. End the story. and it will take longer than you think. So, if you don't like the idea of going I don't know how many of you heard Lucas talk this morning, but if you don't like the idea of going out and pitching and pitching and pitching and pitching because you're going to get a lot of nos and you're going to have to learn, um then you're going to have a hard time transitioning into that CEO role. So, think about how you like spending your time. I was thinking about um so okay what what advice if you know it's worth what you're paying for it but what advice could I give or what things do you need

to think about if you're want to develop the skills or you want to think about what do I have to do in order to become a CEO I've got six I'm going to run through real quickly I will say that I I spoke to a general one time and we were talking about leadership and he said you know my job as a leader is to set strategy get the right team in place to execute the strategy and make hard decisions like That's my job. I think that my job as a startup or an early stage CEO is a little bit different. So, I've got six, not three. Um, but it's pretty consistent across these areas.

So, this first one, team building and management. I talked a little bit about that before uh with HR. Um, but it's really important that you think about recruiting the right team. And I'll tell I'll tell a quick story that's not exactly related to this, but um I was fortunate enough how many people know Okami, the company Aami? Yeah. So I was really lucky. I got to join Okami in 1999. I was their first sales leader and the first 10 sales people worked for me. I hired him. Um and that company was started by a PhD math professor from MIT by one of his students um who tragically passed on 911. Um and they they came up

with this idea to solve a problem. A guy named Tim Berners Lee who was thought to be one of the inventors of the internet. He presented to the class and um and so they had this idea about how to solve the problem and this goes back quite a way. So they literally printed something up and put it in like the lunchroom at MIT business school and said anybody want to help us write a business plan and a guy named Jonathan Celick volunteered. Um but the point of the story is uh Tom Leighton the professor Danny Louu and the student were realized very early we're not the guys to build this company. So they recruited a guy

named Paul Sean to be president and then they even went further and recruited a guy named George Canadius to be the CEO and if you look at the life of that company uh George was the CEO for about six or seven years then Paul became the CEO for six or seven years and the interesting point is Tom Dr. Tom Leighton the PhD founder of the company the heavy the great technologist he became the CEO after about 10 years 12 years of the business running and has been it for the last six years. So, you know, maybe the point of this is, look, you all ought to try it if you want to, but you don't have to do it first. Maybe

you go and get some experience and learn what it's like to work in a business and learn from somebody who's done it, and then you can always circle back to it later. Communication. Um, technologists often want to, again, Lucas said earlier, you know, you have to, you can't speak engineering to investors. You can't speak engineering to salespeople necessarily, not to all customers, not to board members. You have to understand how to communicate about subjects that are not just technology. And so again, if I was if I was in your shoes and I was a technologist and I was thinking about starting my first company, one of the things I would think really hard about is how do I how do I explain what

I'm doing to people who aren't technologists? uh how can I talk to a friend who maybe is an attorney or my mother or whatever it may be and explain what I'm doing to to him or her because that communication with people who are not technologists is going to be critical. I can tell you at the board level uh when I speak to our board and it depends a little bit on the exact board member but they don't really want to hear about the technology problems. They care a little bit about the product because they want to I mean when when they made the decision to invest they care but what they really want to know

is what problem are you what I said before what problem are you solving and why will people pay for it now and how big is the market and none of that has to do with the bits and the bites of the technology. So you really have to think about how are you explaining and how are you able to communicate without technical jargon and in ways that business people or uh even just sort of the lay person is going to understand customer centricity. Uh the only thing that matters really the only thing that matters is are you solving a problem that people will pay to solve today. That is the only thing that matters and is it implementable.

um this company sixmap when I took it over um we had an unbelievable capability a very very powerful capability but the founder didn't build in some of the core foundational elements that you need to sell to enterprise so if you don't have MFA if you don't have SSO if you don't have an API if you don't have documentation all of these things matter a lot and the enterprise will not buy it without that even if you solve a painoint if you can't fit into their stack and you can't integrate with their other technologies, they will not do it. So you have to think about the big picture and put yourself in their shoes and say can I actually use this today?

And if you can't you you know the comp the product is not sellable. Go to market. Has anybody sold anything in here before? Yeah. Selling is a lot different than building technology and go to market is about more than selling and go to market today is completely different than go to market 20 years ago. The the how fast the world is evolving with and I hate to use the term but with AI and how AI is used in marketing today and used in selling today, it's completely different. But you have to be prepared to sell. I was just on a panel um one of our investors had a portfolio get together and I was a panel sitting next

to a guy who's a CEO of a startup and we were there to talk about how do you move from a PC to a to recurring revenue contract and he sits there and he said and I like the guy like I really like the guy we were drinking later what but he said you know one of the ways we've had success is we don't sell you know what we do is we build relationships and we talk about what the problems are and I'm looking at him I'm like That's like that's that is self and I literally I couldn't contain myself. My wife always gets mad at me because I'm I'm not I'm not good at holding back my thoughts. So

at the end before I said when I I happen to be asked the last question and I'm like look I just want to say it. I'm like Dan I I like you and I hope you don't take offense but like you can't sit up here and say you don't sell. If you don't sell you shouldn't be the CEO. Lucas said earlier today usually the first million to3 million dollars of of sales from a company has to come from the founder. So, you have to be prepared to get out there and sell, and you have to be able to do it. And that means asking hard questions, listening to lots of nos, um being able to handle

rejection, and again, recognizing that it's the big picture of how you fit in everywhere that's going to get you to close business. Learn to make hard decisions. I was really lucky that I uh I at at RSA a few years ago. I was um uh at an investment banking conference and the CEO of Cisco was being interviewed by Kevin Mandy. And uh the first thing I'll say is I was blown away how the CEO of a you know $40 billion whatever company. Every question Kevin asked he he I mean he was on top of everything. It was unbelievable that he knew the details of the business as well as he did given how big the company

is. But the only thing I remember from that talk, the only actual phrase I remember from that talk, I don't remember the question, but what the CEO of Cisco said is, "When a decision gets to me, and forgive my language, I'm quoting." This is actually what he said in a room of several hundred people. When a decision gets to me, I have to choose between two shitty options. Because if there's a good choice, my team would make it. Or there, you know, two good choices, they'll pick one. If there's one bad choice, why do they need me? But when there's two hard choic you have to pick between two hard ch hard hard hard hard hard hard hard hard hard

hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard hard op options I have to make that call and I will tell you you have to be comfortable making decisions that are going to cost people their job that are going to change the course of your business you may have recruited a team on the idea that people want to buy blue cars and after talking to customers what you find out is they want to buy yellow cars and so you have to change course and you have to convince your team that the right thing to do now today is to

sell yellow cars not blue and people might have bought bought into that first mission. Um, making hard decisions is actually really hard. Um, I just was in a situation where I had to make a very hard decision about a person and their role at the company. And what I said to our head of HR because it was like it really it was very complicated personal decision. I'm like what I'm trying to accomplish is I want to be able to go to sleep at night feeling like you like I want I don't want to lose sleep over this. I want to feel like I made the right call. And um and that's hard. So you and and the other thing is you're

not going to have perfect information. So a lot of times technologists are used to gathering data, building models. You know, you're not going to have that. So you have to be prepared to make a hard decision knowing that you don't have all the information. And you'll notice there's I don't know if you can read it all, but there's a lot of orange on this slide because at the end of the day, you know, when you're a technologist and I don't know what your backgrounds are, but if you've been in academia and you had to work to work on your dissertation or you're just coming out of being a student or you had a very, you know, kind of a technology

role at a company and now you're about to launch into a career building a business. Um the sometimes the hard part to think about is it's all about the business. The technology problem or you know building a cool technology it very well could build could be a failed business. So you have to think about what's involved in the business. You have to be prepared to understand a financial statement and to explain to an investor what the what the business model is and why what the multiple you're looking for on an exit might be or whatever it may be. Why you can defend a valuation. You have to be prepared to understand indemnification in a contract because your attorney is

going to tell you, "We can't sign up to indemnify them for this or that and you got to make the decision. Can't we do that?" You have to be prepared to stand up in front of people and give us give a talk and get people excited about what you're doing. You have to be willing to understand a little bit about the regulations in your industry so that you can make sure you're compliant and you're not going to get sued for something. This is all part of the business that has nothing to do with technology. And maybe the hardest thing to understand if you've never run a company before is you know obviously what I put in bold at the end is cash is

oxygen to a business and you have to be prepared to manage cash tightly which again requires very hard decisions which requires a lot of detail. I tell you, every Monday the beginning of I start my week with our fractional CFO looking at how much cash we have, looking at what our spend is and making sure that our models, you know, nothing has changed significantly in our model that's going to cause us to change what we've told the board and what we've committed to. It's all about the business. The technology is important, but the business is what's going to make you successful. And so I'll reiterate what I said kind of at the beginning which is um you know

we wanted a slightly provocative uh uh title for this. Um but the point of this talk is absolutely not to say the point of the talk is absolutely not to say you cannot be a successful uh a technologist cannot be a successful CEO. There's lots of examples of technologists being successful CEOs. But there's a lot more examples of technologists failing as CEOs because they don't pay attention to what's needed to actually run a business. They fall in love with the solution. They fall in love with their technology. They don't stay focused on am I solving a problem that people are willing to pay for today. And so my last comment to you is um my closing thought

is really just think hard about what you like to do. Uh, think hard about how you want to spend your time. Think hard about what you're willing to spend your time doing like the financials and the legal and all the other annoying things that we have to deal with. Um, do you want to sell? Um, and and and just make sure that you're building the skill sets so that you can fill check all those boxes because it's going to be required of you as a CEO. So, I built this to spend leave a little bit of time at the end. So, we've got a few minutes if anybody has any questions. Yes. >> How did the board sell you on joining

six? Uh so I I knew the investors. This is my se this is my second CEO role of a cyber company. And when I was uh the first time I got to know the investor community really well like again like networking getting to know people building your um your your your friend network. It's all really really important. So when when I left the last role I told them I was available. After a few months they called me. Um I was I was excited about the opportunity to work with them. uh investors. Again, Lucas said earlier, it's a marriage and I've worked with challenging investors before. Um I was excited to work with them. I became

convinced that the technology innovation was powerful and I became convinced that the tools that were in use today, it's a crowded market that we're in, but I was convinced that the tools that were in place today were not delivering to the market. So, that there was an opportunity for disruption. And I also think cyber um cyber is unique in that um you know if I'm selling a marketing technology the the head of marketing at Bank of America is not going to call the head of marketing at JP Morgan and say hey we bought this new tool that's really working great but the CISO of Bank of America or whatever whatever said Bank of America might call the CISO of JP

Morgan and say hey I found a new tool that really works well those those people do and and so the opportunity to scale a business inside I mean It's really, really hard, but if you get it right, the opportunity to scale is amazing. And I wanted that shot. >> Yeah. >> How do you know when to give up versus like keep going? >> Um, that that that's a really really hard question. Um, I don't I I don't know that I have a great answer for it. I think you have to um I think that becomes a very it's a very personal decision even though like the first company I was a founder of I literally

sat in people's kitchens while they were writing $50,000 checks and I took it very very personally and it like for five years it like it screwed me up and um and ultimately we sold the business and we had a reasonable outcome but throughout we had to ask ourselves that a long time and a lot of it was like what do I personally want? how much pain am I willing to endure because being a CEO is not easy. Um, but a lot of it was also how compel how strongly I felt to deliver back money to the investors. So, I don't know that there's an easy question for that. I mean, there are certain signals you're you're going to

see or you're not going to see in terms of you're going to market. Are people buying? Is it repeatable? Um, why are they not buying? Do you think you can can fix that? Um but I think at the end of the day it's it becomes a very personal decision about how much pain are you willing to take. >> Yeah. Yes. >> How do you go about delivering non ideal um I guess feedback to the team about like maybe things about like direction or market or things that are not great to hear but like you know needs to be said. How do you go about delivering that? Um, there's a couple people that work at our company in the audience and

I you can ask them if if what I'm about to say is true, but I um I'm just I personally am just super direct, super transparent. I explain things the way that I think they really are. I I when I introduced myself to the company, I said I am a pragmatic optimist. I believe you have to like you have to have faith and you have to believe you're going to succeed, but you got to have your feet on the ground. And if we're not willing to deal with the hard reality of what's true, we're going to fail. And so I for me my style is just tell it like it is. And uh and and and still like try to

paint the most optimistic picture I have because people need to believe but not lie, not you know. So um stylistically you have to feel you have to determine what's authentic for you and works for you. But for me it's just I just flat out tell it like it is and also why am I still excited? Um usually try to think about how we're going to resolve that situation. I don't just explain a problem, but here's what we're doing to fix it. Um, that's what I do. I think we're out of time, so I'll be happy to talk answer any other questions in the end, but thank you all for your time. [applause]