Latest / Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth / Scaling the Fastest-Growing Data Security Startup

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Scaling the Fastest-Growing Data Security Startup · Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth

• 0:41
  SPEAKER_00: All right, well, welcome everyone.
• 0:44
  SPEAKER_00: You would have to be under a rock in the past two or three years not to have seen the momentum building up at Sierra.
• 0:51
  SPEAKER_00: I've seen people I know go there, I've seen funding announcements, I've seen industry commentary.
• 0:57
  SPEAKER_00: You just feel looking at uh from the outside in, there's something happening at Sayera, which is why I'm delighted to have Steve Ruj, the VP of Sales at Syara, join us today.
• 1:09
  SPEAKER_00: Steve, welcome.
• 1:10
  SPEAKER_00: How are things going with you today?
• 1:12
  SPEAKER_01: Thank you.
• 1:12
  SPEAKER_01: Thank you.
• 1:13
  SPEAKER_01: Uh very exciting times.
• 1:14
  SPEAKER_01: Things are going well.
• 1:15
  SPEAKER_01: Appreciate it.
• 1:16
  SPEAKER_01: Appreciate the time.
• 1:16
  SPEAKER_00: Yeah, this will be fun.
• 1:17
  SPEAKER_00: We've got a couple of different things to cover.
• 1:19
  SPEAKER_00: Um first thing, the reason I I kind of even reached out in the first place, Eve.
• 1:25
  SPEAKER_00: I don't know if you saw where I showed on LinkedIn about this, but uh I did uh uh some analysis using Richard Steen and IT Harvest dashboard about the fastest growing COVID baby uh cybersecurity companies and using headcount as the proxy for for growth.
• 1:42
  SPEAKER_00: And uh I my other criteria was not name whiz because that would kind of blow the chart a little bit.
• 1:48
  SPEAKER_00: And you know, top of the line was Island.
• 1:50
  SPEAKER_00: Uh I've uh had Eric Apple as the head of sales of Island on the podcast uh about two and a half years ago, actually, just as they were getting going.
• 1:57
  SPEAKER_00: So they've gone from strength to strength.
• 2:00
  SPEAKER_00: Um and then in uh obviously behind Wiz, I had Colin Jones from Wiz on a couple of years ago now, actually almost a week, uh my episode with with Colin, who was the first CRO over at Wiz.
• 2:11
  SPEAKER_00: Uh we took it from zero to up to that 100 million announcement.
• 2:15
  SPEAKER_00: Uh so he was on.
• 2:17
  SPEAKER_00: And now Sayara, based on the analysis I did, is is next one up, right?
• 2:21
  SPEAKER_00: So you guys are on a heck of a tear.
• 2:23
  SPEAKER_00: You can't read this graph.
• 2:25
  SPEAKER_00: Uh basically what I'm saying is that uh there's 15 companies growing really, really fast by headcount.
• 2:30
  SPEAKER_00: Uh top without Wiz is Island, second without Wiz is Syara.
• 2:35
  SPEAKER_00: So this is uh good time for for everyone.
• 2:38
  SPEAKER_01: Very exciting times, yeah, and and all friends.
• 2:41
  SPEAKER_01: So know those guys well.
• 2:42
  SPEAKER_01: Great people.
• 2:43
  SPEAKER_01: Uh we we spend a lot of time talking to each other.
• 2:45
  SPEAKER_00: Yeah, Cyberstarts originally companies as well, right?
• 2:48
  SPEAKER_00: Yes, yes, both correct.
• 2:50
  SPEAKER_00: All right.
• 2:51
  SPEAKER_00: Well, we are recording this live on LinkedIn.
• 2:53
  SPEAKER_00: If you're if you're watching in on the feed coming through, put questions into the chat area if you have any, and uh we'll filter through them and see what we can get to.
• 3:04
  SPEAKER_00: But Steve, first of all, let's get to know a little bit more about you.
• 3:08
  SPEAKER_00: Um so I have, believe it or not, a list of 49 personal questions here.
• 3:15
  SPEAKER_00: The good news is I don't ask you 49.
• 3:18
  SPEAKER_00: I have this completely random number generator here, and it does an amazing thing.
• 3:23
  SPEAKER_00: It's actually so advanced I have to protect it.
• 3:26
  SPEAKER_00: Uh, I'm using uh, you guys don't know this, but I'm using Sayra's DSPN to protect it so no one can steal my algorithm behind the scenes here.
• 3:34
  SPEAKER_00: And it's gonna spit out three random questions for you.
• 3:37
  SPEAKER_00: Let me just uh hit the button here.
• 3:39
  SPEAKER_00: Trust me, there's some some stuff going on in the background.
• 3:42
  SPEAKER_00: Let's see what it throws up.
• 3:48
  SPEAKER_00: All right, the first one is number 19.
• 3:51
  SPEAKER_00: How did you make money as a kid, Steve?
• 3:53
  SPEAKER_01: Oh boy.
• 3:54
  SPEAKER_01: Um, first generation American.
• 3:57
  SPEAKER_01: So uh I can tell you that uh my parents were were very committed to me working early in life, and so uh my wife but or my mom actually made a uh fake ID for me when I was 15 years old so that I could work at the uh the local grocery market.
• 4:12
  SPEAKER_01: Um and then soon after that, my dad pushed me into uh working on roofs.
• 4:18
  SPEAKER_01: And uh as a guy that's uh afraid of heights, I think that was a little bit by design.
• 4:22
  SPEAKER_01: He wanted to uh show me you know what hard work meant and uh really pushed me to you know to continue to educate myself so that I didn't have to do the uh the manual labor that I uh so desperately didn't want to do while uh while he was forcing it.
• 4:36
  SPEAKER_01: Your mom got you a fake ID though?
• 4:38
  SPEAKER_01: Yeah, she was she were she worked at a bank and she laminated basically a fake ID when I was 15 because in order to work at the grocery store you had to be 16.
• 4:47
  SPEAKER_01: So she made me an ID that suggested I was 16 years old so I could start working when I was 15 years old.
• 4:52
  SPEAKER_00: At least she didn't get the old 21, right?
• 4:54
  SPEAKER_00: True story, true story.
• 4:55
  SPEAKER_01: Yep.
• 4:56
  SPEAKER_01: I was uh you know doing the typical pushing carts and then working in produce, the whole, you know, all the fun of it.
• 5:01
  SPEAKER_00: Very good.
• 5:02
  SPEAKER_00: All right, let me press the the random generator here again and see what we we get to.
• 5:11
  SPEAKER_00: All right, number 29.
• 5:13
  SPEAKER_00: What's a memorable moment in your sales work life that you want to share with us today?
• 5:19
  SPEAKER_00: Oh, memorable moment.
• 5:21
  SPEAKER_01: Um, there's there's quite a few.
• 5:23
  SPEAKER_01: I've I've had the great fortune of working for some incredible leaders um that have really kind of shaped uh kind of how I go to market.
• 5:31
  SPEAKER_01: Memorable, you know, to tell you a funny story, uh I'll never forget when I was at F5, we did a QBR in the city in downtown Chicago, and uh my SC and I were outside the restaurant, and I remember seeing Vince Vaughan, and I was so excited, you know, local Chicago celebrity, big cubs fan.
• 5:49
  SPEAKER_01: And I ran up to him and I was like, Vince, you know, huge fan of I take a picture with you.
• 5:53
  SPEAKER_01: And he goes, Why don't you turn around and run right back to where you came from?
• 5:58
  SPEAKER_01: And I was like, Oh, all right, well, that's a pretty humbling experience.
• 6:01
  SPEAKER_01: That's that's certainly that that that got a lot of laughs because my SCs, you know, felt felt, didn't feel short of uh telling everybody about that moment.
• 6:09
  SPEAKER_00: Well, they say you don't meet your hero sometimes, right?
• 6:12
  SPEAKER_00: There's there's an example why you don't do that.
• 6:14
  SPEAKER_01: I have a different uh uh perspective of Vince Vaughn from that day moving forward.
• 6:18
  SPEAKER_00: Yeah, that's unfortunate, right?
• 6:19
  SPEAKER_00: All right, let me let me hit the number again and get the last completely random question out of here.
• 6:29
  SPEAKER_00: Number two, what is the story behind you getting your first role in cybersecurity sales?
• 6:36
  SPEAKER_01: Um, so I uh I studied computer engineering thanks to my brother-in-law.
• 6:43
  SPEAKER_01: So I I was I was studying the engineering at DePaul University.
• 6:47
  SPEAKER_01: They uh they had a course called Junior Experiential Learning, which, you know, the course credits were really to kind of push you into the field um to get a job in, you know, the career that you aspired to go into.
• 6:58
  SPEAKER_01: And uh my brother-in-law was working at Checkpoint at the time, and there were a number of value-added resellers that he went to to ask if I could do a 10-week um kind of a course and and work at uh one of the partners.
• 7:11
  SPEAKER_01: And I had the great fortune of working for a company called Consult Tech, where I started a little bit in engineering and then quickly made the decision that I wanted to be in sales and uh never looked back since that moment.
• 7:22
  SPEAKER_00: And uh was it an easy transition from the engineering side into sales?
• 7:26
  SPEAKER_01: For me it was.
• 7:27
  SPEAKER_01: Uh, I think I was early enough in my career.
• 7:30
  SPEAKER_01: I was, you know, 20 years old.
• 7:32
  SPEAKER_01: Um, so for me, you know, being a people person was always, you know, kind of where I aspired uh to kind of leverage the technical skill set that was given to me at uh at DePaul.
• 7:43
  SPEAKER_01: And so I never really worked on the engineering side of the house from the beginning.
• 7:47
  SPEAKER_01: So that yeah, it was an eat an incredibly easy transition.
• 7:49
  SPEAKER_00: Good for you.
• 7:50
  SPEAKER_00: Good good career after making that switchover.
• 7:55
  SPEAKER_00: Well, let's talk about data protection, Steve.
• 7:57
  SPEAKER_00: So quickly, uh I'm gonna talk about myself.
• 7:59
  SPEAKER_00: Uh I'm gonna make a big faux pas here and talk about myself quickly.
• 8:02
  SPEAKER_00: I sold my first cybersecurity product in 1998, believe it or not.
• 8:06
  SPEAKER_00: And it was an email and file encryption product.
• 8:10
  SPEAKER_00: Uh and since then I've sold uh DLP, uh both network and host-based DLP.
• 8:14
  SPEAKER_00: I've sold laptop uh encryption, data access control.
• 8:17
  SPEAKER_00: I sold encryption again at another company.
• 8:20
  SPEAKER_00: My basically my threat through my whole career is around data protection.
• 8:23
  SPEAKER_00: So I've kind of got the scars along the way about what it's been like, you know, over the years to actually try and get attention and try and get people to buy stuff.
• 8:32
  SPEAKER_00: And you know, one of the kind of takeaways is that I I almost felt like people had great intentions to protect data, but they almost backed off a little bit.
• 8:39
  SPEAKER_00: Saying, well, if we screw it up and don't get it quite right, we could really do some bad stuff here, we could hamper the business, we'll get execs complaining and all the rest of it.
• 8:46
  SPEAKER_00: Let's just not quite do it in the best way.
• 8:49
  SPEAKER_00: And in fact, you know, the dirty little secret about DLP back in the day was most of it was DLM.
• 8:54
  SPEAKER_00: It was DLO's monitoring, not actually preventing too much because people don't want to block.
• 8:58
  SPEAKER_00: So let's fast forward to today.
• 9:01
  SPEAKER_00: Modern uh data protection, DSPM space.
• 9:04
  SPEAKER_00: What's the state of the world of DSPM right now?
• 9:08
  SPEAKER_00: What are security teams actually looking at and viewing the role of DSPM in in the world?
• 9:14
  SPEAKER_01: Yeah, I mean, it's it's a it's a hot category, no question.
• 9:17
  SPEAKER_01: Um and I think there's excitement around the fact that there's actually technology and modern architectures that are actually allowing you to solve those problems, right?
• 9:26
  SPEAKER_01: I think historically it's been a very manual effort and and uh and one that was incredibly difficult to achieve given uh the vast volumes of data that exist within the enterprise space.
• 9:37
  SPEAKER_01: So I think uh one of the great fortunes that SIR has is that we were, you know, we were built three and a half years ago.
• 9:43
  SPEAKER_01: So we were able to really take advantage of modern architecture and you know the world of large language models and you know, machine learning.
• 9:51
  SPEAKER_01: And it it it gives us the ability to actually scale to the the volumes and vast size of uh our organization's data set.
• 9:58
  SPEAKER_01: So that's making people very excited.
• 10:01
  SPEAKER_01: Uh I think they're still very skeptical on on the ability to actually go and chew through these amounts of data and have that level of speed and accuracy.
• 10:09
  SPEAKER_01: And when you can demonstrate that, it it becomes very powerful and uh the the interest gets very high.
• 10:15
  SPEAKER_00: Aaron Ross Powell And I always think I always remember thinking about it as people want to know where their data is.
• 10:19
  SPEAKER_00: There was like the discovery, there was the finding aspect of it, there was the policy aspect, and then there was maybe some sort of enforcement.
• 10:26
  SPEAKER_00: Where is DSPM now, where's the air, I guess, now in terms of actually being able to enforce as well as uh using policies and discoveries?
• 10:33
  SPEAKER_01: Aaron Powell Yeah, it it's all those things, but I think it's it's getting even bigger than that, right?
• 10:37
  SPEAKER_01: When you start looking at AI and the fact that you can now actually enable the business to monetize all that data that they have to really understand where is our data, what is our data, you know, how can we protect our data, and how can we enable the business responsibly to utilize that data.
• 10:53
  SPEAKER_01: So outside of just the threat landscape, you're also seeing the business start to want to monetize that data and use AI applications internally, building their own homegrown or using third parties, but they have a fundamental responsibility to make sure that they're securing that data while they're enabling it.
• 11:10
  SPEAKER_01: And that's I think where Sierra comes in in a big way.
• 11:12
  SPEAKER_00: Trevor Burrus, Jr.: Yeah, there used to be a thing where we did uh DLP engagements was in the Redot, we we wanted legal in there, we wanted HR in there because you know there's implications.
• 11:22
  SPEAKER_00: We found things in the POZ.
• 11:24
  SPEAKER_00: There's real things that you had to change.
• 11:25
  SPEAKER_01: Aaron Powell 100%.
• 11:26
  SPEAKER_01: We talk constantly about creating a coalition of the willing.
• 11:29
  SPEAKER_01: You know, it's it's it's also what makes the cell pretty hard, right?
• 11:32
  SPEAKER_01: You're you're talking to a lot of different personas.
• 11:34
  SPEAKER_01: Um there's a ton of different value use cases across all the practitioners in the company.
• 11:39
  SPEAKER_01: And so, you know, it's it's what makes enablement so fundamental to what we're doing at Syrah.
• 11:44
  SPEAKER_01: We invest quite a bit in enablement, and uh that's why, because there's there's value that's being um you know realized across the entire organization.
• 11:52
  SPEAKER_01: And so you you have to have many different personas inside of your meetings because there's there's things that enable the business and there's things that protect the business.
• 12:01
  SPEAKER_01: And you know, we're fortunate to play a part across the entire chasm.
• 12:04
  SPEAKER_00: Aaron Powell And you acquired a company, I think, called Trail, was it uh a year ago, two years ago?
• 12:08
  SPEAKER_00: Is that fully embedded now?
• 12:09
  SPEAKER_00: Is that is that doing real DLP for you?
• 12:11
  SPEAKER_01: Yeah.
• 12:12
  SPEAKER_01: So you think about the fact that I think we announced that acquisition of Trail about six months ago.
• 12:17
  SPEAKER_01: Um so to have that fully integrated, uh, I think we just announced that most uh most recently.
• 12:22
  SPEAKER_01: It's it I think it demonstrates uh the the power of our engineering and product management teams.
• 12:27
  SPEAKER_01: Which is uh an explicit differentiator for us as a company.
• 12:30
  SPEAKER_01: Like our company uh from an engineering perspective is is best of breed.
• 12:35
  SPEAKER_00: In the DSPM space, um there's the kind of legacy on-prem players moving into cloud, and then you have the newer like Sayara players in the cloud, kind of maybe trying to move into the on-prem.
• 12:47
  SPEAKER_00: Is that what Sierra is looking to do, cover everything everywhere, or are you focusing just on the on the cloud?
• 12:52
  SPEAKER_01: No, focusing everywhere.
• 12:54
  SPEAKER_01: Um we announced our on-prem capabilities about 13 months ago.
• 12:58
  SPEAKER_01: Um so definitely have our roots and started within the cloud in SaaS space and now have uh you know embarked on the uh the objective of you know really kind of protecting the company and giving them that visibility regardless where the data resides.
• 13:11
  SPEAKER_01: Um that's been you know a focal point in listening to our customers.
• 13:16
  SPEAKER_00: Okay.
• 13:16
  SPEAKER_00: Let me uh clearly what you're doing is working, right?
• 13:19
  SPEAKER_00: Uh you see the everything that's going on.
• 13:21
  SPEAKER_00: I I found your your March 2025 press release that came out.
• 13:25
  SPEAKER_00: You used some pretty pretty interesting words, right?
• 13:28
  SPEAKER_00: Uh fastest world world record, fastest growing data security company.
• 13:33
  SPEAKER_00: I don't know if it was I I don't know.
• 13:34
  SPEAKER_00: I read some of this, Stephen.
• 13:36
  SPEAKER_00: You can comment or not comment.
• 13:37
  SPEAKER_00: You know, outpacing even the most successful security firm.
• 13:41
  SPEAKER_00: Kind of alluding maybe that you're you're you're saying you were kind of going faster than Wiz was back in the day.
• 13:46
  SPEAKER_00: I don't know.
• 13:47
  SPEAKER_00: I'm reading, am I reading too much into this, or is this kind of you know how you're trying to thread the needle a little bit on saying what you're doing?
• 13:52
  SPEAKER_01: You know, I'll I'll leave that commentary to Jason Clark, who is uh a masterclass of all things uh strategy and his marketing team that uh reports up to him.
• 14:03
  SPEAKER_01: We've we've had a forced multiplying effort from them.
• 14:05
  SPEAKER_01: But you know, what I can tell you is we admire WIS.
• 14:09
  SPEAKER_01: I don't I don't think there's any startup that uh should suggest otherwise.
• 14:13
  SPEAKER_01: Um and I think that uh you know we have our objectives and we're we're really executing on those objectives.
• 14:20
  SPEAKER_01: And uh you know, we we we maintain a very you know customer-obsessed kind of culture, and that's really driving uh positive results for us.
• 14:29
  SPEAKER_00: Yeah.
• 14:30
  SPEAKER_00: One question for you since you brought it up, right?
• 14:32
  SPEAKER_00: I mean, I I wonder um how much pressure there is sometimes internally to a company such as Sierra, right?
• 14:39
  SPEAKER_00: That people benchmark themselves.
• 14:41
  SPEAKER_00: We've got to go as fast as Wiz and it's just this thing, you know they hit this and they hit that.
• 14:45
  SPEAKER_00: Is that something that you feel a sense around you, or do people kind of recognize you you can't expect everyone just to be going that fast like they were?
• 14:53
  SPEAKER_01: Um speed is definitely at the center of our culture.
• 14:57
  SPEAKER_01: And uh, you know, we we don't it it's it's our own kind of fabric, and certainly bringing Frank Slootman onto the board uh continues to really kind of push the speed.
• 15:07
  SPEAKER_01: Uh you know, the outcomes that we're seeing internally are very tangible.
• 15:12
  SPEAKER_01: So when when you see that, the entire company, like the sum of all parts, are operating with speed.
• 15:18
  SPEAKER_01: And speed is a force multiplier for the company, right?
• 15:21
  SPEAKER_01: It allows us to do a lot of things and and that's what's happening.
• 15:25
  SPEAKER_01: You know, there's there's speed across the company in engineering, there's speed and and even legal.
• 15:29
  SPEAKER_01: Like you start to look at the sum of all parts, you know.
• 15:32
  SPEAKER_01: I think I think sales and go-to-market always gets a lot of the spotlight, but internally at Syrah, what's allowing us to have this success is that the entire company is operating with speed.
• 15:41
  SPEAKER_01: And when you have that across the foundation of a company, the outcomes become very real realistic.
• 15:47
  SPEAKER_01: And so speed, speed is something that we uh we will always center on and focus on in terms of executing as fast as possible.
• 15:55
  SPEAKER_01: Because at the end of the day, you know, we're trying to help our customers achieve what they're looking to accomplish.
• 16:01
  SPEAKER_01: And speed is necessary.
• 16:02
  SPEAKER_00: Yeah, for sure.
• 16:03
  SPEAKER_00: Aaron Powell Let's go back to November 22, Steve.
• 16:05
  SPEAKER_00: I think that's the month that you joined Sayara.
• 16:08
  SPEAKER_00: What did you think you were gonna be doing in the first few months of joining?
• 16:12
  SPEAKER_00: And and was that uh what reality was, or did everything change in the first few weeks there?
• 16:17
  SPEAKER_01: You know, when I first joined, uh I knew the company was gonna be successful.
• 16:21
  SPEAKER_01: Did I think it was gonna be um successful as fast as it's been?
• 16:26
  SPEAKER_01: No.
• 16:26
  SPEAKER_01: I mean, I'd be lying to you if I suggested otherwise.
• 16:29
  SPEAKER_01: Um but I, you know, I give a lot of credit to the founders, you know, Yotam, Tamar, um, and and the team, because they they really allowed and gave latitude to a lot of the people that they hired.
• 16:40
  SPEAKER_01: And they really they gave us the ability to build the foundation, right?
• 16:43
  SPEAKER_01: So, like if I told you, Andrew, my first two hires were not salespeople.
• 16:47
  SPEAKER_01: It was ahead of operations and it was ahead of sales engineering.
• 16:50
  SPEAKER_01: And they did not come cheap.
• 16:51
  SPEAKER_01: You know, they were very uh very successful throughout their careers.
• 16:55
  SPEAKER_01: And when we made that decision as a company, it started to kind of permeate across uh all business units.
• 17:01
  SPEAKER_01: And I think what that allowed us to do was really put ourselves in a position to build a strong foundation for which then we started to really grow on.
• 17:08
  SPEAKER_01: And uh, you know, we had early success.
• 17:11
  SPEAKER_01: Uh, you know, we made a lot of very deliberate hires in the in the first six to twelve months, and uh it became a snowball effect, right?
• 17:19
  SPEAKER_01: Like you start seeing success and you just continue to iterate on it.
• 17:22
  SPEAKER_01: What's an example of a deliberate hire that you made that we might be surprised about?
• 17:26
  SPEAKER_01: Um I I my first hire was head of operations.
• 17:29
  SPEAKER_01: Um and he has been uh a godsend to the company.
• 17:32
  SPEAKER_01: And um, you know, a very deliberate hire were my first three salespeople that I'd worked with them in the past and you know, they came here and and found immediate success.
• 17:42
  SPEAKER_01: And it you know, in the early days, you know, we were when I joined, I think the company was maybe a year old.
• 17:49
  SPEAKER_01: Um so we were buying time, right?
• 17:51
  SPEAKER_01: We were buying time, and and the only thing that affords you to do that is revenue.
• 17:55
  SPEAKER_01: And so we were able to put some revenue on the board quickly, and that bought us some time, and then you know, products started to really outpace, and then we started to be able to really lean into the investment and kind of run a little bit hot on expense and start to to really kind of invest into the company.
• 18:11
  SPEAKER_01: And and it proved uh it proved very successful because then the the cohorts continued to to deliver, and um, you know, now we're here today.
• 18:19
  SPEAKER_00: Aaron Powell I remember when I was talking to Colin when he was at Wiz, he said, you know, you had to tear up the headcount plan every six weeks because they were just you know growing so fast.
• 18:27
  SPEAKER_00: Um They does kind of raise the question.
• 18:29
  SPEAKER_00: Like, you know, you said you had your first three hires you knew and then you layered on cohorts after that.
• 18:33
  SPEAKER_00: How did you know or what metrics did you use, or what was the kind of internal planning to say, yeah, now is the right time to add the next cohort?
• 18:39
  SPEAKER_01: Aaron Powell Yeah, I've I've I've I've been fortunate in that you know I started my career at Foundry and then worked at F5 and then you know went to Four Scout.
• 18:49
  SPEAKER_01: And so I've seen different levels of companies, you know, multi-billion, hundreds of millions, and then went startup.
• 18:55
  SPEAKER_01: So I I knew what good looked like and I knew what you know what timing looked like in Tor in terms of really pressing the gas pedal.
• 19:03
  SPEAKER_01: And we've also across the company have incredible guidance from not only our board, but also, you know, I have the fortunate luxury of you know talking to guys like Adam Ahrens and Dave Schneider and you know Dan Fugiri, I'm having dinner with in two weeks, like guys that I really want to emulate and really learn from and and understand what they did and when they did it.
• 19:24
  SPEAKER_01: Um I spend a lot of time talking to Jordan from uh from Wiz as well.
• 19:28
  SPEAKER_01: Um we probably talk, man, maybe two, three times a month.
• 19:32
  SPEAKER_01: Uh so I lean on I lean on you know folks that have done it before me and in this at this level and this speed, because there's not a there's not a lot of them out there.
• 19:40
  SPEAKER_01: And uh and I take guidance and then I make you know some of the decisions and we we work together as an executive team incredibly well.
• 19:48
  SPEAKER_01: And uh it's a collective effort.
• 19:49
  SPEAKER_00: Yeah.
• 19:50
  SPEAKER_00: So you you figure out from their advice about when to start uh pushing or or or pulling back a little bit in different areas.
• 19:56
  SPEAKER_01: Well, you you at least get their perspectives.
• 19:58
  SPEAKER_01: And the more perspectives you have, the more you know you have the ability to make an informed decision.
• 20:03
  SPEAKER_00: Yeah.
• 20:03
  SPEAKER_00: One of my clients right now is kind of wrestling with this a little bit.
• 20:05
  SPEAKER_00: They they're growing faster than they thought.
• 20:09
  SPEAKER_00: Um and one of the surefire ways to really piss off a salesperson is to mess around with their territory every few months, right?
• 20:16
  SPEAKER_00: But you have to do it, right?
• 20:17
  SPEAKER_00: A fast-growing company, right?
• 20:18
  SPEAKER_00: There's only so much the world that you can take.
• 20:20
  SPEAKER_00: So what have you learned about how to manage that whole setting expectations and then handling transitions and trying to keep people who are doing well motivated by not you know taking away stuff all the time?
• 20:30
  SPEAKER_01: Aaron Powell Yeah, we we you know we made the very calculated decision early on to set ourselves up in a in you know the pyramid approach.
• 20:38
  SPEAKER_01: So we focused on the G2K from the get-go.
• 20:40
  SPEAKER_01: So people's territories haven't really changed much because from the from the beginning, you know, everyone had uh a list of named accounts.
• 20:47
  SPEAKER_01: You know, the only way to really measure success and to see what's getting done is to have focus and to see what kind of uh what kind of gains are we making within the accounts that we really want to consider our ICP.
• 21:00
  SPEAKER_01: Um so we we we took a very measured approach to make sure that we did this the right way from the beginning so that you didn't have this situation where you know people, you know, the company is growing and people feel like they're they're losing things.
• 21:12
  SPEAKER_01: They're they're not not at Sierra.
• 21:14
  SPEAKER_00: And if I'm an enterprise rep at SIRA, how many accounts am I covering then?
• 21:17
  SPEAKER_01: Aaron Powell Um It depends.
• 21:18
  SPEAKER_01: So we we've we've now somewhat segmented into three different uh tiers.
• 21:22
  SPEAKER_01: And so you know you have your traditional kind of majors that are you know probably right around 20 accounts.
• 21:28
  SPEAKER_01: Enterprise has anywhere from you know 50 to 70, and then you know the commercial team that's more geographic.
• 21:33
  SPEAKER_00: Aaron Powell Yeah, so that's 50 to 70 is way plenty to deal with, right?
• 21:36
  SPEAKER_01: Aaron Powell Still Yeah, I mean we have we have a lot of room to grow.
• 21:39
  SPEAKER_00: Yeah, yeah.
• 21:39
  SPEAKER_00: I mean I I remember back in the day always people get upset, oh, I want to go 25 accounts.
• 21:43
  SPEAKER_00: Well, how many have you reached in the last six months?
• 21:45
  SPEAKER_00: Well, you know, 10.
• 21:46
  SPEAKER_00: Okay, well, you got some room to get to get going, you know?
• 21:48
  SPEAKER_01: Aaron Ross Powell Yeah, and and the and the smart the smart reps you know um will realize that they'll they'll actually do more with less.
• 21:55
  SPEAKER_01: I know it's uh it's an old adage that people fight, but the the truth is, you know, you talk to you know successful sales reps, when they've made the most in their careers is when they focused in on three or four accounts and you know really gave uh you know their best effort into those into those accounts.
• 22:10
  SPEAKER_00: Yeah.
• 22:11
  SPEAKER_00: You mentioned enablement before.
• 22:12
  SPEAKER_00: I noticed in March 24, you brought in your head of sales enablement.
• 22:16
  SPEAKER_00: Why was that the right time, basically just over a year ago, to bring that person in and start building on a function?
• 22:21
  SPEAKER_01: So that was when so we we we made an investment internally on enablement even before that.
• 22:26
  SPEAKER_01: So we had an ind an individual.
• 22:28
  SPEAKER_01: I mean, you want to talk about selfless, we moved him from in one executive position into you know at that time we were saying enablement was the number one thing that was that was the number one thing my biggest block that I wanted to tackle and had a very selfless individual who went into that role and started you know building the content, building the practice and then we made the the the huge investment of building that out into a full-blown team.
• 22:52
  SPEAKER_01: And the reason for that is uh you know my job is to try to reduce ramp time as much as as possible.
• 22:59
  SPEAKER_01: And the only way to effectively do that is to really enable people as they come in.
• 23:03
  SPEAKER_01: I think our onboarding and enablement um as people come in and they they get into boot camps.
• 23:08
  SPEAKER_01: I think it's world class.
• 23:10
  SPEAKER_01: I'm incredibly proud of what the work you know the team has put together in that in that in that category.
• 23:16
  SPEAKER_01: And so we we made a collective uh decision as a company that that was going to be something that we were going to invest in and I'm I'm really proud that we made that decision.
• 23:23
  SPEAKER_00: Aaron Ross Powell People have all sorts of different metrics about how to measure ramp time and make it faster.
• 23:27
  SPEAKER_01: What what are the ones that you guys have settled on uh there's there's a number we we uh from a data perspective we we crunch a lot of internal uh numbers but you know it's dynamic.
• 23:38
  SPEAKER_01: I don't think there's any you know static uh attribution that you can really look at for ramp time but um you know we have we have reps that have come in here and closed business within their first 30 days.
• 23:47
  SPEAKER_01: Um for me I really consider you know a fully ramped rep is when they're producing quarter on quarter on quarter the amount of pipeline that's required to to meet the objectives and you know they've they've hit a run rate not necessarily that you know they've had a successful quarter.
• 24:03
  SPEAKER_01: I want to see the consistency and you know proud to proud to you know tell you that our first court you know as of uh the beginning of this year on average we are at 136% you know achievement across the board.
• 24:14
  SPEAKER_00: So that's an awesome yeah I always think when when teams are growing fast, business growing fast, the temptation sometimes is to cut corners a little bit, right?
• 24:23
  SPEAKER_00: We're we're salespeople, we're trying to find the the easiest and fastest ways to make numbers.
• 24:27
  SPEAKER_00: And remember actually I do remember this two years ago I think it was at least the Claude Flair CEO went on an urgent call and said that he realized that during their huge growth phase much of their sales team and he used the phrase had become order takers and when the market changed them they didn't really know how to sell that well and he was kind of really you know surprised and upset.
• 24:46
  SPEAKER_00: So I guess you know how you thinking about enablement how you think it about your you know leadership team to say look we got to do this properly.
• 24:52
  SPEAKER_01: Yeah again we we we invest a lot in enablement not only internally but also externally so we're we're a we're a very big uh advocate of the force management methodology um so cutting corners doesn't really exist um as much as we subscribe to the science of professional selling we also very much uh appreciate the art that's behind it too so I don't want us to become a culture where it's just uh kind of a machine and there's there's there's no art and there's no um you know genuine FaceTime with customers.
• 25:24
  SPEAKER_01: I think one of the things that we do incredibly well is show up and be curious.
• 25:28
  SPEAKER_01: Um you hear that a lot from from most sales leaders like you want to continue to have that curiosity um and you want to you want to be professional so you want to be disciplined about the way you run your campaigns.
• 25:39
  SPEAKER_01: And I think that's what we've done from an enablement perspective incredibly well.
• 25:43
  SPEAKER_01: And now we're really getting into you know spending an adequate amount of time with with frontline leadership.
• 25:48
  SPEAKER_01: I think it's the most important job, most critical job in a company.
• 25:51
  SPEAKER_01: And so we're we're really doubling down on what we do to make sure that we enable those people to be incredibly successful as well.
• 25:57
  SPEAKER_00: Yeah it's funny first level first line management um you know you ask a hundred you know heads of sales and they'll say yeah there's most important people super important all the rest of it and say well what are you doing to help them you know be great managers and leaders and then they kind of start looking at their feet and looking the other way and changing things up, right?
• 26:13
  SPEAKER_01: Aaron Powell Guilty, right?
• 26:15
  SPEAKER_01: I've I've been there before um you know you kind of expect so much from those people but you don't really invest the time that's necessary.
• 26:22
  SPEAKER_01: So you know we do skip levels.
• 26:23
  SPEAKER_01: I I myself I have 30 minutes on the on the books with every single frontline leader every month uh in the company.
• 26:30
  SPEAKER_01: And you know we we we do use third parties to really train and elevate uh you know make sure that we're making the investment in them so that they they know what's expected, what's required and they feel like they're getting enabled and they feel like they're getting the resources from the company to do their job well.
• 26:43
  SPEAKER_00: Aaron Ross Powell On the last episode that we did, last live I did actually last week we before Rob Umesqua the head of sales at Force Guy was on and we were talking I was talking to him about what sort of people he looks for in that first level manager.
• 26:57
  SPEAKER_00: What about you, Steve?
• 26:58
  SPEAKER_00: What what what's important to you for your first level managers?
• 27:01
  SPEAKER_01: Yeah I I tell a story about it um because you know I I look I look for people that have the passion and what I mean by that is like do you remember when you played some structured sports either high school or college?
• 27:13
  SPEAKER_01: Remember that grind?
• 27:15
  SPEAKER_01: Like you'd wake up in the morning it would be like weight training then school then two hours of practice you'd run home try to eat and do homework without falling asleep at the kitchen table.
• 27:24
  SPEAKER_01: You did all those things because you wanted to win not just exist.
• 27:28
  SPEAKER_01: You wanted to be the best.
• 27:29
  SPEAKER_01: And somewhere along the way I feel like um people lose that passion as they get into their career and it's kind of mind blowing to me right because if you think about our careers it should be something that we love doing.
• 27:40
  SPEAKER_01: You know it's what brings food to the table for our families.
• 27:43
  SPEAKER_01: Like it should be something that we want to continue to educate ourselves and invest as much as possible.
• 27:49
  SPEAKER_01: So I look for people that have that level of passion regardless on how long they've been in the industry.
• 27:54
  SPEAKER_01: I look for that even if they've never done frontline leadership before I think that level of investment into the company is what really starts to differentiate those that'll be good at the job and those that'll be great at the job.
• 28:09
  SPEAKER_00: So I look I look for the the attributes within people not necessarily what they've done previously that is you know promoting from within right it's the classic thing well you're a great salesperson we'll make you into a leader and then you know people don't realize that there's overlap in terms of the job function is only about 20% yet we just expect them to figure out the other 80%.
• 28:28
  SPEAKER_00: How you how are you thinking about you know internal promotions in that role?
• 28:31
  SPEAKER_01: Aaron Ross Powell It's incredibly important to me and I think the reason that you see 20% success rate is because of what we talked about you know five minutes ago.
• 28:37
  SPEAKER_01: I don't think that businesses appropriately enable people to be frontline leaders.
• 28:42
  SPEAKER_01: Like think about it it's not just a skill that people become awesome at like you have to either A have a leader on top of you that's training you and giving you a bunch of attention to learn how to do that job effectively or B you know the company has to make an investment to make sure that you're getting trained properly on how to be a frontline leader.
• 28:59
  SPEAKER_01: And that's that's why we we take those investments so seriously.
• 29:02
  SPEAKER_01: I mean I'm of the opinion that you know promoting from within it would be like the number one path um so long as the the the the folks that are running for those positions are capable and they have those attributes that I talked about earlier.
• 29:15
  SPEAKER_01: And then we can we can make the investments to train them on how to do things from a from a science perspective the right way.
• 29:22
  SPEAKER_00: Yeah.
• 29:22
  SPEAKER_00: It's uh it's such an important role but it seems like people you know I don't know you always feel like there's more bang for the buck to invest other places rather than that first line but uh I would do it differently like you are I feel like if you're gonna suggest it's the most important role in the company, then there's a requirement to make the investment to train those people.
• 29:41
  SPEAKER_00: Absolutely I mentioned to Eric Apple the head of sales island that you and I were going to talk and he said to say to Steve, congrats on the rapid success and the value you guys are driving.
• 29:51
  SPEAKER_00: Great to see the innovation execution.
• 29:53
  SPEAKER_00: I would love to get your thoughts on how things change on the journey and these are his numbers he threw out there you know from bigger 100 million plus versus the first zero to whatever you're at right now.
• 30:05
  SPEAKER_00: So you know how are you thinking about things the need to change and and focus the the the go to market.
• 30:10
  SPEAKER_01: That's a really good question.
• 30:13
  SPEAKER_01: And it's it's one that I think about a lot, right?
• 30:16
  SPEAKER_01: Because you know my responsibility is to continue to to have that consistency.
• 30:20
  SPEAKER_01: You know, we're 14 quarters in a row of sequential growth.
• 30:24
  SPEAKER_01: I was looking at you know the um the spreadsheet that you kind of gave and and in the uh the company that is uh you know I saw the metrics for the company I forget the name of it what was uh Cyberdonut.
• 30:36
  SPEAKER_01: So I was looking at that and I saw you know last year Q1 was greater than the previous year's Q4 but then this year Q1 was far lower than Q4.
• 30:47
  SPEAKER_01: And so um I looked at that and I was like that wouldn't fly at Sarah.
• 30:53
  SPEAKER_01: And and I think about that question quite a bit because you know there's always the suggestion of you know the people who got you to 25 aren't necessarily the people who get you to 50 aren't necessarily the people that get you 100 and beyond.
• 31:06
  SPEAKER_01: I don't subscribe to that.
• 31:07
  SPEAKER_01: I I think you know so long as we continue to execute at a very high level um so long as we continue to monitor all the attributes that define a you know a healthy business um so long as that we continue to make the investments in our people and we we hire at a you know we maintain the bar of hiring at a very high level and we'll continue to execute and so that's the sole focus is to to really make the investments in the proper areas of the business and and just continue to push forward.
• 31:36
  SPEAKER_00: I feel like that whole you know is the person the right person to get you from here that got you there and all that sort of stuff.
• 31:42
  SPEAKER_00: I think it all depends on hey the person, but also uh how proactive they are right you look at someone like like Eric at Island right he was the first go-to-market almost person there, right?
• 31:51
  SPEAKER_00: They came in and started building the team immediately he's still there they're doing really well building someone like Ty Fag at Tanium, you know, it was in the first three salespeople at Tanium and now he's you know whatever it is 10, 11 years later he's you know the CRO.
• 32:05
  SPEAKER_00: You have to have the right person and if you can proactively make the changes and adapt and do the right things, you know, that's how you set yourself up to really be the right person going forward.
• 32:15
  SPEAKER_01: I completely agree.
• 32:16
  SPEAKER_01: I think I think there has to be a level of humility for the individual to know what they're actually not great at and then make the investments in yourself to get better.
• 32:24
  SPEAKER_01: No one's perfect at everything right out of the gates and uh I think if you have the humility to be self-aware and know where maybe your blind spots are and then seek the advice and counsel of how to how to rectify some of those things and make the appropriate changes um then I think you're putting yourself in a position to be successful long term.
• 32:43
  SPEAKER_01: And so that's the culture we kind of permeate throughout the entire company.
• 32:46
  SPEAKER_00: All right let's change things up a little bit Steve.
• 32:48
  SPEAKER_00: We're gonna finish up here with something a bit more lighthearted than uh than go to markets uh planning and and execution.
• 32:54
  SPEAKER_00: Um it's time for a section I call visionary or high.
• 32:57
  SPEAKER_00: I'm gonna throw out some bold predictions about the future of sales and cybersecurity sales.
• 33:02
  SPEAKER_00: You tell me I'm I'm I'm I'm in Colorado am I a deep thinking insightful visionary or did I wake and bait this morning with some Colorado gorilla glue before getting to my desk.
• 33:12
  SPEAKER_00: All right.
• 33:13
  SPEAKER_00: Okay.
• 33:13
  SPEAKER_00: I like this this is fun.
• 33:15
  SPEAKER_00: So you just have to tell me am I visionary or high?
• 33:18
  SPEAKER_00: Here's number one by 2030 so five years 80% of cybersecurity purchases under 100K will happen without a human seller or a human buyer just AI agents buying and selling is that visionary or am I high?
• 33:35
  SPEAKER_01: High not by 20 not by 2030 and yeah I fear the day that that's uh that's the case no I I don't think that's happening by 2030.
• 33:44
  SPEAKER_00: Where would you do the where where would you draw the line?
• 33:46
  SPEAKER_00: Let's say by 2030 is it 50 K uh ASP?
• 33:49
  SPEAKER_00: Is it 20 K?
• 33:50
  SPEAKER_00: Is it 5K?
• 33:51
  SPEAKER_00: It's gonna happen somewhere, right?
• 33:53
  SPEAKER_01: It's gonna happen somewhere I I think I think a hundred what were we initially what was the original hundred K.
• 33:57
  SPEAKER_01: 100K too much um I think you know trivial things that uh you know 100K is that's a that's a significant ASP.
• 34:07
  SPEAKER_01: I'd say I'd say somewhere you know somewhere along the lines of what in today's world corporates giving people a credit card that they can swipe and buy like I think that that stuff will happen within the next five years.
• 34:17
  SPEAKER_01: So somewhere in the lungs of 20 maybe 20k all right yeah that's that's uh that's interesting.
• 34:22
  SPEAKER_00: It's gonna be somewhere it can't be zero and 100 is too high right won't be zero.
• 34:27
  SPEAKER_00: All right in 10 years time both the RSA conference and black hat will be dead completely gone visionary or high?
• 34:36
  SPEAKER_00: High.
• 34:37
  SPEAKER_01: Tell me more too many people enjoy it too much um just in general yeah in general and it's you know it it it it truly fosters an environment where I think practitioners get to get the most out of one week.
• 34:50
  SPEAKER_01: You know it it's where they find out a lot about technology that they won't necessarily have the time to do and put you know again talking about continuous education like I think that that week gives gives people that don't have you know time on their on their side to to go and consume as much knowledge as possible within you know five days.
• 35:10
  SPEAKER_00: All right next one the biggest threat to a cybersecurity seller success right now isn't the competition it's their own ability to inspire a prospect to change is that visionary or is that high?
• 35:24
  SPEAKER_01: That's true.
• 35:25
  SPEAKER_00: Yeah that's that's uh I I subscribe to that yeah the the inaction is is what uh is hard to overcome sometimes all right uh here's one two more by 2030 Shadur Saunders will have won a Super Bowl visionary or high?
• 35:41
  SPEAKER_00: High tell me more not so long as he's in Cleveland so at least he needs to move to a new team right I think so all right this is coming from a Bears fan though so I don't know that uh play the one here you gotta you gotta think carefully about this one this is probably my my most insightful question so recently Google announced they're requiring Wiz and some hacks in the industry called the combination G Wiz so within 12 months the OT security company that's called Insane Cyber will buy the other OT security company called Sanctuary and the combined company will be will be renamed to Insane Asylum.
• 36:22
  SPEAKER_01: Is that visionary or is that uh high I don't know a lot a lot about those companies but I'd say that's high it's gonna happen though you're gonna you're gonna have a CEO go yeah we should do that we should go and acquire those guys and change the company name oh that's incredible well Steve listen this has been uh good fun chatting today appreciate all your insights um I know you guys are hiring if someone wants to get in touch and jump on the on the train how do you go about doing that uh re reach out I mean proactively through the website through LinkedIn um you know there's there's there's tons of leaders who just reach out to directly to us um yeah very excited thank you for the time today andrew uh enjoyed it greatly yeah it's been a blast thanks for joining us yeah absolutely