The ABC of Success – Always Be Closing – Bob Kruse (CEO, Low Rider Security)

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Detailed transcript :

Bob : People are smart and they’re very intuitive. I would say that don’t do it with an agenda. Do it without an agenda. Just do it because you want to help. Just do it because you love what you do and you’re passionate about helping people. I don’t do it with the expectation of getting anything in return from them.  


Neelima: Hello everyone. Welcome to another episode of Zero to Exit. This is Ankur and Neelima, your hosts. On today’s episode, we are delighted to have with us Bob Kruse, Co-founder and CEO of Low Rider Security, an early stage cybersecurity startup in stealth mode. Prior to starting Low Rider, Bob was CRO at Obsidian Security, Head of sales at Demisto, which was acquired by Palo Alto networks for $560 million. He’s also held sales, leadership roles at BlueCoat, FireEye, F5 and other large security companies and is also an advisor to many cybersecurity companies as well. In today’s show, we’re going to talk about all things, enterprise sales, how the role has changed over the years and where we are heading.

If you are a technical founder of a B2B startup and are of the mindset that “if you build they’ll come”, you definitely don’t want to miss this episode. 


Hi, Bob. Welcome to the show.

Bob: Thank you for that wonderful introduction. It’s an honor and a pleasure to be here. I hope to help.

Neelima: great. So I want to start this show by asking both of you. If you got in on the GME action?  Bob, I will start with you first.

Bob: No, interestingly enough, I started my career in investment banking and I convinced myself at a very early stage in my career that I’m horrible at investing. So I just stayed out of it. So I have the attention span of a goldfish, so I couldn’t do it. 

Neelima: How about you Ankur?

Ankur: Oh, I got hooked and unfortunately I do not have an investment banking background, so I did get burned, luckily not a lot. It was fascinating, a lot of fun and there’s going to be ramifications. I think my favorite line coming out of this whole GME saga was, I think one of the Redditors motto was “ we will remain retarded longer than you can remain solvent, to stick it up to the hedge fund.” So I thought that was funny. (Laughs)

Bob: Yeah, I love the Elon Musk involvement as well. 

Neelima: I’m a very, very slow learner. So even though I invest, I’m so glad I didn’t get any of that action for the last five days. 

We’ll start with your career then Bob. So very early in your career, there’s a story you started with selling carpets. How did you get into it? And from there into selling enterprise software. Tell us a little bit more.

Career Trajectory 

Bob: It’s a great question. So the story starts with watching the movie Wall Street with Michael Douglas, Lunch is for Wimps. Right. So if you remember that movie Wall Street, I was convinced when I was going through college at Gonzaga University studying Economics, I wanted to be Gordon Gekko, I wanted to be an investment banker.

And so before I graduated, I interviewed with all the investment banks and none of them would hire me. That time, Gonzaga wasn’t really well known. They didn’t have a good basketball team like they do today. And everybody I talked to and they all had great interviews, great contacts and they’re like, well, you need to get sales experience before you come and apply.

So, I decided that I had a job offer from a carpet company, a commercial carpeting company and I thought that would be an excellent way to get sales skills improved and prove I can sell anything, including carpeting. You can pretty much ask me about carpeting, anything about carpeting today and I can tell you way more than you’d want to know and way more than I care to share but it’s all in the brain. So that’s how I got into carpeting and it was the first real job out of college to prove to the investment banking community that I could sell. So I did that and I had carpet samples in a van, et cetera but I completed that. 

And then I moved to San Francisco and got a job at an investment bank.  I worked on the options exchange. I worked for a place called Robertson Stephens for folks that are old, like me that remember investment banks in San Francisco. And I became a sales trader. I had series seven, six 63, I was the guy with all the phones and the screens and screaming at nobody in particular. And one of the things we were doing on those trading desks was helping companies public and one of those companies was eBay. And I’ll never forget the day, we were part of the consortium that took them public. And I remember them ringing the bell. And I remember the person that rang the bell, I think was a janitor at eBay who is now a billionaire. And I decided right then and there that I needed to be on the other side of the screen. And so I resigned from investment banking and the first job I could get in tech was at Oracle. And so that’s how my tech career started. And then there’s more from there but that’s essentially how I got into technology. It was by way of carpet. (Laughs)

Learnings from Oracle

Ankur: fascinating. Yeah. Huge fan of Wall Street, Boiler room, Wolf of wall street. I was just listening to one of the exchanges between Matthew McConaughey and Leo when he gets introduced and he’s all struck by it. Yeah, I can totally see it. It’s a  pretty fast paced 18 hour work day environment kind of craziness. When you got into Oracle, it was and still is an  iconic company and has a pretty amazing sales culture.

Were there things in Oracle that you learned about selling and selling to businesses, obviously that was your stepping stone. What are some of the key learnings from Larry Ellison and Oracle?

Bob: At Oracle, I quickly learned about things like politics and some things that you wouldn’t readily admit that were useful but ended up being useful. It’s a numbers game in terms of how many dials did you make, how long did you spend on the call? Did you call the right person? It was very metrics driven for the time. It was a very metrics driven dial for dollars numbers game type of thing. And it was very political and very competitive. The person next to you, who could be your cube mate in fact, when we were back in office he could possibly steal a deal from you just overhearing you. So it was a very cutthroat environment, it may not be that way today but at the time it was. It was a great learning experience about how to stay positive, how to stay active. One thing I had on my monitor at Oracle, I’ll never forget was “what can I do right now?”.

So there’s always something whether it was a phone call, a piece of research or an email, there was always something that could further my goal and no matter how small or big it was, there was always something to do at any given minute of the day as long as you had a goal. It was like, just keep going, keep going, keep going, keep going and persevere. It’s not so much the person that does the best. It’s the one that lasts the longest. (Laughs)

Neelima: So Bob, you mentioned a cutthroat environment. You also mentioned how to stay positive, that is very fascinating to me because you’re so competitive. In the same organization in the same team but then you have to stay positive as well. How well do those two things work together?

Bob: Yeah, I mean, it’s a bit of a contrast because you’re in a team and you need to have cohesiveness. At that time, it was Oracle versus Sun, Oracle versus Microsoft, you’re competitive internally which helps breed excellence in regard. I mean, in theory probably. (Laughs) but you need to stay true to your integrity. And that’s one thing that I’ve always prided myself on is that I’d never lie, I’d never cheat. I’d never take anything from my teammate or anything like that. And at that time it was really hard because I saw a lot of people stealing deals from friends or from each other and benefiting from that financially and career-wise but it never seemed right to me. It was part of I guess my Catholic upbringing. I always just felt guilty because I was Catholic. I don’t know why I just felt guilty (Laughs) but in any case it was always trying to be the nice guy and still trying to win at the same time which was always a struggle.

Neelima: We heard you a lot of times in Demisto saying, “everyone wins or loses together”. Is that from where it comes from?

Bob: Well partially. At the time at Oracle, I was struggling with should I be cutthroat? How do I be more cutthroat? How do I be more selfish? Should I be more selfish? And so I would say again, not to impugn Oracle at all, it’s just my experience or my viewpoint but it was always a struggle. And how do I be more selfish and competitive and cutthroat yet stay true to my integrity.

Winning and losing together came mainly from FireEye, which is further along my career. The gentleman by the name of Jeff Williams, who’s my friend and mentor today. He is now at Bain Capital, kind of inspired a lot of that.  And a lot of things like sales become kind of evangelical in a way but in any case that, or at FireEye, a lot of that started because I feel like in my career it is where I really blossomed. 

FireEye and Operation Aurora

Ankur: Yeah, it’s a perfect segue because that’s what I was gonna have this conversation go. So, you joined FireEye, pre IPO, part of the IPO, spent four years and for the  listeners out there, FireEye within four to five months, post IPO went up almost 200% to 300%. The stock jumped. It was the talk of the town. If you’re in Bart on Caltrain, everybody’s talking about- “Oh, do you know this guy from FireEye just became a millionaire”. This is back in the days when a stock going a hundred percent in four months was a big deal which I know today people take it for granted. So, we would love to learn your observations or learning on the path up as FireEye grew so quickly so fast and then I want to then talk about it’s sort of decline from its glory days. So I’d love to get your perspective

Bob: Yeah well, I’d like to attribute my departure to it’s decline. (Laughs) No, I’m kidding. All kidding aside, that’s not true. FireEye is a classic Silicon Valley story. It was a startup that wasn’t really a startup. It had been kind of rolling around for, like I said, four or five years and then in 2010 I joined. And, it was right when, if anybody remembers, Operation Aurora happened. Highly publicized, first nation state attack on an enterprise. And it was really FireEye- I’d like to say  “Oh my God, I had it all figured out. And I knew where to go. I knew what to do. I knew what to say”. It’s like the saying “Luck is the intersection of preparation and timing.” So, I was in the right place at the right time as a result of what I’d been through and who I knew and the experiences I’ve had. So it’s kind of hard to say, this is exactly what you need to do to reproduce that because it was really just luck in a way. But at FireEye, we started it. It was like I had one sales person and I need to fire that person and rehire. And the first person I hired was  Chelsea Strong, if I may use specific names and I hired Chelsea out of, I think she was at McAfee or something and she was going to Symantec and I literally started anyway, nothing against Symantec but I just talked her out of it. (Laughs)

Ankur: She is thankful to you for having done it. 

Bob: Oh, she’s a personal friend. She’s wonderful. We have worked together at FireEye as well for a while and then we’ve worked together ever since.

Ankur: I don’t think a lot of our listeners really understand Operation Aurora. Can you do a quick 30 second on what happened? And maybe talk a little bit about the sandboxing technology. It was not commonplace back then. What happened? How did the whole market macro environment plus the technology kind of collide and in that process, obviously you and a lot of people got lucky deservedly. So, can you demystify that for our listeners.

Bob: Okay. Yeah. Operation Aurora. And I think full disclaimer, dangerously technical in sales here. So, it was the first nation state attack and there were more before that, after that and everything but Operation Aurora was the first publicized and widely advertised nation state attack on all, not all but a lot of the most prominent technical and otherwise enterprises that I’m sure we don’t even know about today because they didn’t have disclosure laws back then. But that was saying “Hey, China has infiltrated all these companies and exfiltrated all this data. And it became something that entered the public conscience and everybody was wondering like, Oh my God, what’s a hack? What’s a hack? And so now people like my mother and my grandmother and people that are technical understood what a hack was. It’s like- wow, you can do that. You can hold up a bank and steal money from it without actually being in there with a gun. You can do the supply chain attacks or stuff like that. So, it really became the heart of the conversation on a nationwide status in terms of like- Hey, we know what hacking is and it’s something that’s bad. And it’s something that other countries do to us. Yeah. We might do to them too. (Laughs) But anyway, so it became something that was part of the national consciousness. It became part of the national vocabulary. It became part of the national knowledge. And so people didn’t really know what it was technically, but they knew that it was bad. And what happened with Fireye was that we were there and we realized that wait but I have antivirus software. How did he get past my antivirus software? And taking nothing away from antivirus software but that was antiquated technology. And of course, Operation Aurora proved that it could penetrate that and go right by it. And enterprises realised, we need a new solution for a new threat. And that’s where FireEye came in. And so that’s where we had to execute and did a good job of doing so. And that’s pretty much what precipitated our hockey stick up into the ride through our IPO.

FireEye- what did not go right

Ankur:  Yeah, who knows how many companies will solar storm now take to the IPO and many, many more will come. Now, obviously you left FireEye and it’s not the same company it was before. We all have perspective, right? Like part of what happened was sandboxing zero day, which was sort of a new thing, became commonplace. Everybody started copycatting but I’m sure there are others. I’d love to get your perspective on sort was it lack of innovation, obviously losing you (Laughs). What is the big thing that happened that it’s not the same company anymore.

Bob: Yeah. They’ve taken some steps recently. That’ll be interesting to see how it evolves. I obviously have a ton of respect for Kevin Mandia and everybody that’s running the team there and Chris key, et cetera. So, again, I don’t want to impugn FireEye at all but you know, it’s a constantly evolving thing.

And that’s the beauty of cybersecurity. At any point in time where you think you know everything and you have the right solution- Just wait. (Laughs) Don’t ever buy a product that says zero false positives because it’s just not true. (Laughs) But in any case, at FireEye, it was one of these things where we would have never gone public if it weren’t for Ashar Aziz who founded the company and grew it wonderfully. And it was great technology. And essentially what it was like was instead of- Hey, is this a grenade. Let’s take this, the example was take this grenade and throw it in your yard and see if it blows up and then the shrapnel flies everywhere versus FireEye was like- Hey, take this and put it in a very armored bucket and see what happens in the bucket. And if it blows up in that bucket then it was a grenade. So that’s what FireEye technology was. It was essentially mimicking a victim and allowing the malware to infect it. And then – aha  it’s actually malware. And then from there, the evolution was like how do we prevent that? So once you know more about it, you can get attribution and MD 5 hashes, all this stuff. It was a really, really wonderful Anti APT type of technology, Advanced Persistent Threat technology and then the advent came of Mandia meshed with FireEye. That was primarily a services company, 80% services, 20% product and the challenge was-  all right, now we acquired Mandiant, which is Kevin Mandia’s company who was a phenomenal Vanguard in his field primarily services. And like when the house is on fire, that’s who you call, right. To mesh with a different culture and a different product, which was, we were an appliance, they were a service with product attached to it. Like, how do you bring those two together and still keep the relative kind of stature for each company. And so I think what happened was there was confusion in the marketplace about – are you a service company? Are you competing with the channel or are you creating a product? And what product? It just created some confusion because there wasn’t a clear message or vision. But in and of itself, Mandiant was a wonderful company,  preeminent vanguard in its field. FireEye had pioneered the sandboxing technology, as you say, where you put the grenade in the bucket and so it’s like, how do you bring those two together? And so we’re seeing the evolution of that today, for sure, but it’s still ongoing.

Ankur: Yeah, absolutely. I mean, well said, the downfall or not staying in the glory days is I think a big function in our industry. It’s innovate or die. Well-meaning super sharp people are executing this. I think they dwelled. And Kevin Mandia has just amazing people, sometimes macro conditions, sometimes innovation et cetera. 

Speaking of innovation, you were part of a company right after FireEye which innovated a lot, crushing it in the market, which is BlueCoat. And I think you were there during the glory days. And then you left before the acquisition to Symantec. Generally love to learn any key experiences you have had at BlueCoat but more particularly about how to hire and retain top sales talent. So I’d love to get your perspective on any area at BlueCoat that you’d like to share with our listeners.

Bob: Yeah, first let me say whether it’s my career at Oracle or beyond that, I still maintain very close relationships with everybody, so not going to throw anybody under the bus and I know you’re not asking me to do so. I went from Oracle to a startup in  South of Market, San Francisco and did all that was fun. That was great. I’m not sure what we did but we had fun. (Laughs) And then I went to F5 networks and F5 networks is actually, if I could direct your attention there, it’s an interesting story. And I still have tons of great friends there. And F5 is literally trying to reinvent itself. So if you’re familiar with layer four through seven networking, they’re very focused there. Their core product, which at one point was 80% of the revenues was big IP which is an IP load balancer application. 

Yeah, what do they call it? Eight, eight piece. I don’t know. I got added layer fourth through seven, but, but, uh, uh, they were always trying to .. they are an interesting story because they’re right in Seattle next to Amazon and obviously Microsoft but they could never really figure out what to do with the cloud or how to do it. So it’s a really interesting kind of thing. They’re figuring it out now and they have been. My good friends are doing it, Calvin Rowland, et cetera. And they’re doing a great job but it was an interesting case study. BlueCoat is an interesting thing where we were a proxi plant, port 80,  just straight up proxy, which is a dirty word for networking. 

Ankur: It’s especially a dirty word at Palo Alto networks. You can get fired if you use the word uProxy. (Laughs)

Bob: Well, I’ll let my proxy speak for me. Right. (Laughs). So, yeah, but BlueCoat was interesting. We got preoccupied as a company and I say we including myself, there’s nobody to like finger point, but we got preoccupied with Riverbed. Wide area like what was it WAN acceleration or I forgot what they did. I don’t even know but we decided that security was an afterthought, we needed to go after Riverbed and not what they did. And we kind of lost sight of security and that’s kind of what led to.. Before Symantec, it was a private equity, Thoma Bravo. And right after I left in 2010 and joined FireEye, Thoma Bravo acquired BlueCoat and effectively took it off the public market. And then further down the road, they meshed it with Symantec. It was actually a really good idea. There’s a lot of debate on how well it was executed but yeah, I definitely think that was a good thought and then obviously we know what happened. At the time it was like, we got really preoccupied at BlueCoat that security wasn’t the way to go. What did Riverbed do again, Riverbed is gonna kill me for saying this but something WAN acceleration or wide area, whatever.

Ankur: Yeah, something like that. And that’s okay. 

Bob: But I mean,  it in itself is a kind of case study that we can’t remember. (Laughs)

What separates good sales reps from the great ones

Ankur: Yeah. So, they did the SD- WAN which is obviously WAN acceleration, SD-WAN, which is a big thing nowadays. So, it’s fascinating how in security a lot of these things come through cycles but while the technology in the industrial landscape changes, one thing doesn’t that doesn’t change is really the fundamentals of selling.

Love to get your perspective on hiring and retaining great talent. You’ve had multiple four year runs at companies and with sales teams, it’s really hard to keep that thing. What have you learned about what separates good sales reps from the great ones? What do they do? How are good sales leaders to great sales leaders? What have you learned that some of our listeners who want to get into the business can learn from.

Bob: Well, I would just say it’s like passion and make it personal. And I know that sounds really pedantic but there’s always a better technology, there’s always a better paying job and you can chase money, you can chase stories. But the one thing that people can’t is feeling and personality and they want to be a part of something bigger than they are and that needs to be fun. I’ve worked for and tried to manage as a command and control type of person and I’ve worked for people that try to manage that way basically based on fear. And I understand that tough love has its place but I truly believe that if you trust people and empower them then one of their greatest, no, I wouldn’t say fear but one of the things they never want to do is let you down because you trust them. That’s the kind of people I like to hire because the best kind of person is self-propelled and maybe that’s the Catholic guilt in me but I have this thing where I don’t. I have a fear of failure and I don’t want to let anybody down and maybe I’m a people pleaser and I could go to therapy for that for years. But the reality is that I care more about delivering a solution that makes my prospect look like a hero. I care more about creating a team that allows my team to win.

I care more about them than I do myself. And that altruism is something that people see and feel, whether it be your employees or your prospects and customers because the reality is nobody even knows this story but all too well- life’s too short. It can change in an instant and you gotta make it personal because you’re gonna end up spending more time with your customers or with your employees than you will anybody else because that’s the way we work. Maybe not in COVID now but the reality is that if you don’t make it personal, if you don’t do something you’re passionate about and you have integrity about that, it’s really not worth doing. It’s really not worth doing no matter how much money is involved. And I say that as a salesperson. (Laughs)

Neelima: Yes, I can attest to that having seen Bob’s style very closely. One related question about this- Does sales behave a little bit differently in public listed companies versus startups because the pressure is very different, right? Because when you are accountable to the street, there are very different pressures sometimes. And that can attribute to this behavior or you think it’s just how some leaders behave in sales versus others.

Bob: Well yeah, so essentially you’re asking the difference between like a startup versus a publicly traded company and how that operates, that sort of thing? It’s very, very different. In a startup or a smaller company, there’s nowhere to hide. There’s no run rate business. There’s no PO’s coming over to the fax machine automatically or anything.

Ankur: Yeah. (Laughs)

Bob: In Startups, really every single opportunity, every single email, every single call, every single everything counts and in bigger companies, and again I’m not impugning but it’s just my preference that I’ve experienced in larger companies, there’s a dilution of effort. You have different departments, you have different processes and you have different people and there’s a 16 step process to close a deal, whereas at a startup it’s a two-step process, or something like that. And I’ve been asked- why do you like small companies or startups? And I’m like- well, they’re slightly dysfunctional and slightly disorganized kind of like me. (Laughs)

Ankur: Okay. (Laughs)

Bob: The bottom line is don’t like to hide. I like to own. Maybe a self-admitted control freak, but I can’t stay in my swim lane. I like to understand every single part of the process. And to answer your question, what makes a good sales rep in my mind is somebody that owns every single step of the process. They understand- How they buy, why they buy, when they buy, what partner they use, what kind of terms they use, what kind of paper they use, every single aspect. You’ve heard of the metaphor – how the sausage is made? It’s like the best sales reps in my mind are those that understand how the sausage are made. They understand, there’s a person in procurement. Okay. When are they going on vacation? And when will they be in town? Does it coincide with my expectations and what I need to do? Because you’re selling a firewall to somebody but they might not understand their own procurement process. So it’s almost your job to understand it for them. And in a startup, you need to own every single aspect of that. I would say you need to own every single aspect of it no matter where you work, but it’s harder to do at a large company because you’ve got so many other things coming at you. So, there’s clarity of mission in the startup. There’s clarity of ownership. There’s clarity of accountability.

Neelima: Yeah. So speaking of great reps, after BlueCoat you went to Demisto. 

Bob: No, I went BlueCoat,  FireEye, kind of screwed around a little bit and then went to Demisto. So.. (Laughs)

Neelima: Okay. So, at that point you saw explosive growth that most startups dream about. Is it fair to say you had most fun at Demisto among all your companies?

Bob: Yeah, absolutely. 

Ankur:  That’s a cheating question. (Laughs)

Bob: Yeah, no I did. And at Demist, I attribute it to the team, to the founders specifically Rishi and Slavic. And they encouraged me not to stay in my swim lane, came up with the symphony conference and logos and t-shirts, I just love doing all that stuff, customer advisory councils and then all the while in parallel closing deals and signing channel partners. There wasn’t one swim lane I needed to stay in. I had to cross all of them and I was empowered to do so and I was encouraged to do so. And I really appreciated that.

Can networking be taught?

Ankur: Yeah, I can totally see why you had so much fun at start-up. Your voice obviously lights up when you talk about Demisto and startups. And as somebody who has done it for many years, it’s just an amazing ride. One of the key things you have to do in a startup is obviously leverage your rolodex, your networks and some of the best sales leaders have a tremendous network. And while a lot of people in product engineering, every function talks about networking being a leading indicator of success, career growth, they’re not able to do it. Like some people are just reluctant. Maybe they are not outgoing but they just don’t network enough. You I’m assuming given your rules are tremendous at this craft. Can networking be taught? What have you learned about networking over the years that you can share with our listeners?

Bob: Yeah, the best thing I can say is that people are smart and they’re very intuitive. I would say that don’t do it with an agenda. Do it without an agenda. Just do it because you want to help. Just do it because you love what you do and you’re passionate about helping people. If you do it with an agenda, it’s pretty obvious and I’ve encountered that and that sort of thing. But like you’re really, really in it to help and to further. So I can tell you tomorrow, not tomorrow, next week I have probably four or five calls where I am  helping people that I have no financial stake or anything. I’m just helping them because I like to help. And I know it’s kind of the pay it forward thing. I know it’’ll probably come around or maybe not. I don’t really care. I really just like helping and that really helps my networking where people are like, all right, how do I do this? How do I do that?  Share a channel program or a comp plan with somebody. I don’t do it with the expectation of getting anything in return from them. It’s a kind of a philosophy I have and it’s something that has always benefited me in terms of relationships and people. can sleep at night, so. (Laughs)

Ankur: Yeah. And it’s also about making investment, right? I mean, you have to make a lot of investment upfront, help a lot of people before you start reaping the reward. But like you said, if you treat it as a transactional thing, people will smell that from a distance and just turn away rather.

Bob: Yeah. And you’ll attract transactional people and then you’ll get caught in something that you don’t want to be in.

Ankur: Absolutely.

Neelima: And Bob, what’s the fine line there? Like not having an agenda because at the end of the day when I reach out to Bob, for example, I am asking for help. So there is definitely some kind of agenda and you are investing your time. So what is that fine line where you are a hundred percent sure that it’s actually going to help both the parties.

Bob: No, I’m never sure. I’m really not. I literally go into it. I want to help Neelima, no strings attached. And I think that you have to be pretty clear on that. And, obviously you need to be judicious with your time and time is money, all that good stuff. You know now where I’m CEO and co-founder of my own company, I have to be careful right now. We’re kind of in a quiet period. So I’m loading myself up with a lot of things like mentorships and things like that. I gotta be careful because that’ll come to a screeching halt as soon as our product’s ready (Laughs) but I literally have no expectations. And what I’ve found is actually when you help people, they expect there to be an agenda. They expect there to be expectations and that kind of takes care of it for me, their expectations, or their preconceived notions. It’s just something where I kind of intuitively know where to cut it off as well. And it is kind of the EQ thing but like helping you Neelima, I do not expect anything in return at all. I’m not going to be like- Hey, maybe that one time I introduced you to this one person. Yeah. Well, you owe me this. I would never do that.

Neelima: I think speaking of EQ Bob, I think that’s the difference, right? I’ve seen people sense, which is unique and that’s what I wanted to kind of unravel because that’s just such a soft piece.That’s very hard to kind of judge and maybe it’s the EQ piece. Any insights around that like how do you evolve your EQ as a salesperson?

Bob: Yeah. I mean, it’s definitely a process and a trial by error. I can tell you, like at Oracle, when I made money as a sales rep, they’re essentially auditing existing customers, which did not feel good at all. And I can tell you honestly, that I did not make any lasting relationships with any end users (Laughs) where they’re replicating a database and they owe us another quarter million dollars. That’s not a fun call. But I hit my quota. I didn’t feel good. So I didn’t like it. So earning money and hitting quota wasn’t enough. I always loved delivering solutions that actually matter and work and make them look better. So, you have to identify what’s core to you. And no shame in killing your quota and making millions of dollars a year. There’s no shame in that but that could never be my primary goal. And I know I sound like a boy scout but I could never make that my primary goal to just enrich myself at the expense of others. And it’s kind of personal, it depends on the person but you….

Ankur:  yeah. Play the long game. Right.

Bob:  yeah. I’m truly passionate about it. I went into this industry purposely and I really am mechanical in general. Like I can change oil in my own car and all that stuff. So I like solutions that solve problems.

Ankur: Yeah. So transitioning from obviously history to current and now as if the pain of a startup (Laughs) was not enough, you decided to take on more pain. And, you could have gone into the sunset and said- okay, I’m going to just retire after this amazing run but no you’re starting your own company, Low Rider Security. And I am so happy that you have agreed to finally disclose what you’re working on(Laughs)

Bob: No (Laughs)

Ankur: a launching pad for that.

Bob: Nice Try.

Ankur: I am just joking obviously. Tell us why you decided to start the company. Maybe tell the listeners, at least with zip code, they should look at in terms of what you’re going to be working on or anything you can share. Obviously I’m kidding, you don’t need to share anything more than 

Bob: Well, we were in the same space as GameSpot. No, I’m kidding (Laughs).

Ankur: Oh, okay. I’m buying. Is it a public traded company? Is it a Stack? Why did you start the company? I’d love to know.

Low Rider Security

Bob : It was one of these things where, again, we’re in stealth so I can’t reveal what we’re actually creating. But it was one of these things where I call it my Magnum Opus. It was something I always wanted to do when I left the trading desk in investment banking. I knew that I wanted to do startups and start my own company. And that started from childhood. My father owned his own, my parents own their own heavy equipment company, cruise, tractor and equipment. And I always saw the bane and the benefit of doing that. But at the end of the day, you control your own destiny. And now that was always kind of ingrained in my head, where you need to control your own destiny and rocket science, isn’t rocket science. There’s something, something very romantic and a learning about starting your own company. But in any case, I always had that. So that was just a recurring theme, recurring prompts and it kept coming up and I went to Obsidian security, a wonderful company, wonderful founders. Loved it there. Never intended to do anything else other than obsidian. But I reached a point where I kept hearing the same thing and I just kind of made a decision. I said- if not me, who, if not now, when I’m not getting any younger, I’m 50 years old. And I just decided that this was the time to try along with my co-founder. And, it was definitely a strange time to do it but it’s also a pretty smart time to do it because our potential competitors are either nonexistent or they’re suffering because of COVID or whatever and by the time everything opens up, we’ll be ready to start selling. So that was kind of one of the game things but really just one of these things where we just had to do it. And my mother asked me, she’s like, well, isn’t that really stressful for you and my answer true to me was that it’s more stressful for me not to do it because this is something I’ve always wanted to do. And I’ve made this arbitrary decision that now’s the time and I don’t really care about COVID. I mean, I care about COVID but I just need to do it. So it’s kinda more come back to make it personal, make it passionate. Lo and behold put a pitch deck together and really didn’t have much trouble getting funded, our seed funding. And we’re going to raise an A here in a couple of months and keep going. And I am just very thankful, very thankful. It could change at any second, so we’re very humble as well but a lot of diligence. I’ll tell you that as a first time CEO and founder during COVID, I’m lucky to have any hair left. It took a lot of follicles. (Laughs)

Ankur: Okay. Yeah, no, no, super, super happy with you. One way to lead life is to have no regrets. And I think if that’s something you always wanted to do, then what better time. Are you even able to talk about which segment of security- Net Sec, App Sec? It says Low Rider, so low down the OSI layer.

Second layer, Third layer is security but there is a rider element towards it. I’m thinking it’s network security, but I mean I have no idea. Are you able to share at least which space or that’s also pretty stealthy. 

Bob: We are very stealthy, so I can’t really … Both of you are extremely smart, so you’ll figure it out. I had somebody on LinkedIn and they said – Oh, I get it. You’re going to be securing the next generation of electric cars  and my answer was exactly.

the best thing I can say is that people are smart and they’re very intuitive. I would say that don’t do it with an agenda. Do it without an agenda. Just do it because you want to help. Just do it because you love what you do and you’re passionate about helping people. If you do it with an agenda, it’s pretty obvious and I’ve encountered that and that sort of thing. But like you’re really, really in it to help and to further. 

Sales leaders as founders

Neelima: So I’ ll ask a related question. Sales leaders as founders. Not, not very usual in Silicon Valley but then there’s always a first time. What advice would you give to your fellow sales leaders who want to start a company?

Bob : Yeah, I would say that’s a really great question because that was one of the things that I thought was going to be an issue. And definitely we addressed it with our investors, Very, very go to market, heavy, dangerously tactical, underline dangerous. I mean, for me, it was surrounding myself with the right kind of people that are obviously technical and also being dangerously technical. I understand enough to understand how things work. I can’t make them work but understand how they work. So I would just say that if you’re a go to market person that’s starting a company, make sure your co-founder or the people you surround yourself with are fearlessly technical and make sure that you’re in good company in that regard. And that’s easier said than done but also I would say that,  you need to have a product or something that you have a very good understanding about product market fit from a go-to-market perspective. And, these are just masters of the obvious kind of statements but make sure that whoever you’re partnered with or you’re investing with knows the technical parts better than you but you already know who to sell to and what to sell. So again, super general high-level statements. It’ll all come clear in time but..

Ankur: What is that? Is that a secret as well? Do you have some tentative timeline?

Bob: yeah, I would say we’ll be out in summer and where we’re positioned. My co-founder was with CrowdStrike. He was with me at FireEye and was also with me at Demisto. So, there’s all sorts of people that would be interested but we’re not competing with any of them. (Laughs)

Ankur: Yeah, you should be a politician. (Laughs)

Bob: (Laughs) I’m not. I used to tell Neelima, I’m the resident game show host at my company. So..

Future landscape for Sales

Neelima: All right. Since, you’re not going to talk about Low Rider, maybe we’ll talk a little bit about sales roles. Enterprise sales roles have changed over the years and we’re also seeing consumerization of B2B from that perspective. COVID has also accelerated that trend in a lot of direct selling through the web. So what does the future hold for top-down sales motion in next five years?

Bob: I think if you look at Gong and, there’s always like.. was one of the first companies that had a kind of a hybrid field inside role. But at the end of the day, you had to be really good at telephone skills and demand generation and digital marketing and things like that. Gone are the days where I’ll just hop in my Taurus and drive around and convince people to buy my stuff.Now, there needs to be a really intelligent way of selling and I thought we did a really good job at Demisto, specifically Rishi and you Neelima with the community edition.

That really proved to me that things have changed where cold calling may not actually be the way to go necessarily. But I would say that what’s benefited me is having started, I’ve started from the ground up and inside sales. That really benefits me. And I look for that in people that I interview and hire that they’re not waiting for leads to come to them. They know actually how to go out and find them and have made those connections and made it personal and created that Rolodex. So, I would say that the future of the enterprise sales person needs to be a combination of being savvy with the digital tools that are out there like the Clari and Gongs et cetera. And knowing how those systems work. So for me, what benefited me as an individual contributor was understanding how sales operations worked, how CRMs worked and how HubSpot and Eloqua when that existed worked and lead scoring and stuff like that. So I think that the evolution of the enterprise sales rep is a combination of kind of marketing operations or demand gen as well. 

You need to have more tools in your toolbox. Not only do you have to have a high EQ and great telephone skills and understand how to talk about NFL teams (Laughs), whatever it is that you do, you need to understand also how the plumbing works in terms of digital marketing and digital lead generation. It’s not enough just to be charming and all that stuff. You need to understand the plumbing because that’s what’s going to happen.

Ankur: Yeah, I think you’re right. It’s spot on. Hybrid is the way to go. I think it’s a false dichotomy. Is it going to be top-down? Is it going to be bottoms-up? Well, it’s going to be both. I think if you’re going to take down multimillion-dollar deals, somebody is going to want to talk to somebody who can be trusted. But at the same time, the lead gen has to be product driven. Well said, awesome. That brings us to the final segment. We can do this all day long. I think with your skills and personality, we can have hours and hours but I want to be mindful of your time. So this is the rapid fire round. I’ve got few questions. Yes or no simple answers. All right. It’s going to be fun. I promise you that. So are you ready for that? So the first one is, ust to play on the sell me the pen- sell me GME.

Bob: GME. Well, I’ll tell you, it’s not about GME. It’s about the opportunity to democratize trading. It’s an opportunity. It’s a window into, I guarantee you that the majority of people that were playing had no idea what Gamestop’s all about. They were looking at some sort of a trend or an uptick. And it was a very alerting romantic to kind of beat traditional wall street at its own game. So I think it was the gamification, no pun intended, but it was a game of gamification of trading and beating entrenched in the old school investment banking at its own game.

Ankur: Sold. I am buying. all right. The next one is- I’ve got a scenario for you, just a simple one. Top rep-average region or an average rep- amazing region like a tech company, right? Selling it  B2B. who gets what. 

Bob :who gets what.

Ankur: So are you going to give the top rep an average okay region or the best region? And an  average rep the best region where he can sell, he or she can sell. Who gets what?

Bob: Sales management is proven time and time again. The best thing to do is focus on the top performers. You’ll always get more output out of the top performers. Now assigning regions. I would give my top rep, a crappy region,  or an average region rather than the top performing one. Now, will I give my average rep the top performing one? Maybe not, I’d probably split that territory twice or something like that. I would take that top region and I would split it and I always see what happens from there but that’s how you segment a market. But I absolutely believe in giving top rep to develop a region, do something hard. Show us that it’s you, not your region but if you have a top region, I would probably wouldn’t give it to the average rep. I’d probably split that region.

Ankur: Love it. Do you have a favorite business book?

Bob : I do, Neelima knows a few of these. But I have some books, some are tongue in cheek like What would Machiavelli do? by a guy named Gil Schwartz back in fortune days. I have a book that I recommended or hand it out to everybody which is The Obstacle is the Way, which is really good. I have another one from the Navy. So my dad was in the Navy. I had a military kind of upbringing. It’s called It’s your Ship. And then I can go on but like Five Dysfunctions of a Team for instance is another good one. 

Ankur: Love it. We will put up all these books in our show notes. If you had to be locked in a house with one historical or current figure outside of your friends and family, shelter- in-place, COVID and you’ve got to spend maybe a week or two, who would that individual be? Maybe not a week but a day. Take your pick. Who would that person be?

Bob: Can I say Gordon Gekko, probably not.

Ankur: O yeah.

Bob: I think it’d be pretty fun. There’s some people out there that are well-publicized and we know about like Jack Welch or it would be pretty interesting to talk to some of them. Like Andy Grove, who’s no longer with us but fascinating individuals. And to rather give you a name, I actually like people. Henry Ford is probably, he’s not the best example cause he has some controversy around him but I love the quote when he said “Chop your own wood. It’ll warm you twice.” So, I love people and I kind of fashion myself in the same way that come from meager beginnings and built themselves up.And so I would say that any figure that’s kind of done that is fascinating to me, cause I do this today, socially in a restaurant or whatever. I always try to figure out or ask people what they do and why they do it. I love their stories. The stories that fascinate me the most are the ones where somebody is bootstrapped and lifted them, kicked their own butt first and lifted themselves up.

Ankur: Yeah. The classic American dream and entrepreneurship. Love it. Will humans become multi-planetary species in our lifetime?

Bob:  absolutely. 

Ankur:  Wow.

Bob:  I mean if you consider Stockton another planet so it could be.

Ankur: (Laughs) All right. And the last question,what advice would you give your 18 year old self?

Bob: Yeah. I would get in closer touch with the EQ part, things like body language and just understanding office politics and politics in general. I didn’t really give enough of that credence at 18. I thought it was all crap. And you can either lift a hundred pounds or you can’t. The reality is some of the smartest people, get somebody else to lift that hundred pounds. And that’s the part that I underestimated at 18 and I embrace today.

Ankur:  Lovely advice. Awesome. Well, that pretty much wraps up this episode of Zero to Exit Bob. Thank you so much for taking the time out and obviously you and I don’t know each other but just in this one hour conversation, I can tell you that you’re the kind of guy, I’m rooting for success. So I wish you well on Low Rider security and you are going to crush it just like you have historically and we’ll be keeping an eye on your progress. Thank you so much.

Bob: Thank you. It has been an honor.

Neelima: Thanks. Maybe we can have you after you come out of stealth.

Bob:  I would love that anytime. All right.

Ankur: Enjoy the week.

Neelima: Thanks