Latest / Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth / 114: What I would do differently at the beginning of my sales career

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114: What I would do differently at the beginning of my sales career · Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth

• 0:42
  SPEAKER_00: Welcome to episode 114 of the Sales Bluebird podcast, which exists because at B2B startups, it's hard to get go-to-market fit, grow revenue, and scale the sales team.
• 0:54
  SPEAKER_00: Sales Bluebird provides tips, tricks, experiences, examples, inspiration, and ideas from people who've been doing this for many years and many companies.
• 1:04
  SPEAKER_00: I am your host, Andrew Monahan, and our topic today is what I would do differently if I was starting my selling career today.
• 1:13
  SPEAKER_00: I've had some questions from some of you about topics about your early stages in your career.
• 1:18
  SPEAKER_00: You're looking for ideas, you're looking for tips, things like that.
• 1:21
  SPEAKER_00: So I thought I'd distill that into this topic today.
• 1:24
  SPEAKER_00: Before we get into that though, I am now taking sponsors for this podcast.
• 1:29
  SPEAKER_00: And in fact, got my first sponsor signed up just this week.
• 1:33
  SPEAKER_00: If you want to reach a bunch of sellers and sales leaders in the community, or if you specifically want to reach the cybersecurity sales community, at salesbluebird.com in the top menu, there's a menu option called sponsors.
• 1:47
  SPEAKER_00: And in there it tells you all about the sponsorship and how to go about securing one.
• 1:52
  SPEAKER_00: So go to salesbluebird.com and click on sponsors in the top menu.
• 1:57
  SPEAKER_00: So with my career, I first started selling cybersecurity in 1998.
• 2:02
  SPEAKER_00: Before that, I was doing a couple of other different markets.
• 2:05
  SPEAKER_00: And I got into cyber through the encryption door with selling PGP at the time.
• 2:12
  SPEAKER_00: And then since then, I've sold antivirus, anti-malware, vulnerability scanning tools, DLP, firewalls, web gateway, email gateway, services, security services, instant response services, network tools, uh help desk, sim, all sorts of things.
• 2:28
  SPEAKER_00: I've probably missed a few things out along the way there.
• 2:31
  SPEAKER_00: And I spent 19 years directly in sales, carrying a quota, either as a seller or as a sales leader.
• 2:38
  SPEAKER_00: And then since then, I've spent about eight or nine years working with sales teams as a consultant and trainer and coach to help them succeed in the cybersecurity space.
• 2:49
  SPEAKER_00: I've worked at the biggest companies, biggest brand names, right down to one or two, which are super early stage.
• 2:55
  SPEAKER_00: One was still in stealth mode when I joined.
• 2:57
  SPEAKER_00: We were selling before we even went public with what we were doing.
• 3:01
  SPEAKER_00: And in my selling career, I qualified for eight out of the 12 president's clubs I could have qualified for.
• 3:08
  SPEAKER_00: And three times I was on stage getting awards.
• 3:11
  SPEAKER_00: So that was my career.
• 3:12
  SPEAKER_00: I think by most measures, I did pretty good.
• 3:15
  SPEAKER_00: I feel reasonably satisfied with how things have gone, but really enjoying what I'm doing right now.
• 3:21
  SPEAKER_00: But if I was to do it all again, and let's say I was starting now, or I was early in my career now, what would I do differently compared to how I did things all those years ago?
• 3:32
  SPEAKER_00: So I've got four things I would do differently.
• 3:35
  SPEAKER_00: The first one is I would go all in on security as a market early.
• 3:43
  SPEAKER_00: You know, when I first got into cybersecurity or information security as it was called back in the day, as I said, I got in through encryption and started selling that.
• 3:52
  SPEAKER_00: But you know, frankly, I was I was dabbling, right?
• 3:54
  SPEAKER_00: I was in that mode in my 20s of trying new areas.
• 3:57
  SPEAKER_00: I was too easily distracted about moving roles or moving companies based on OTEs and promotions and you know things like that, right?
• 4:07
  SPEAKER_00: Which was okay, but it meant that I didn't know enough about the wider security market as I got into it.
• 4:15
  SPEAKER_00: I allowed myself just to be trained and just to get knowledge about what it was that I was selling.
• 4:20
  SPEAKER_00: And I wasn't thinking big enough and wide enough.
• 4:23
  SPEAKER_00: I also didn't go big enough and wide enough on my network early on as well.
• 4:27
  SPEAKER_00: Right?
• 4:28
  SPEAKER_00: If you're dabbling in something, you're just not that committed to go and do the extra things needed to truly build a career, build success over time in that area.
• 4:40
  SPEAKER_00: So instead, what I would do right now is I would make at least a five-year commitment to say I'm gonna work in cybersecurity for at least five years, and then because of that, I'm gonna go and learn much more than what I'm just taught at my company.
• 4:54
  SPEAKER_00: I would learn much wider things.
• 4:55
  SPEAKER_00: There is no doubt that we live in a golden age right now of information out there.
• 5:00
  SPEAKER_00: If we want to go and learn something, it is there, right?
• 5:03
  SPEAKER_00: You don't have to go too far on your keyboard to try and find how you could learn about much wider topics in cybersecurity than what you get at your company.
• 5:12
  SPEAKER_00: So that's one thing I would do.
• 5:13
  SPEAKER_00: I would go, I would commit to cybersecurity for a period of time and just say, I'm gonna go and try and be the expert in that area.
• 5:20
  SPEAKER_00: So that's way number one.
• 5:22
  SPEAKER_00: Number two is I would look to build a franchise as opposed to just going to win deals.
• 5:28
  SPEAKER_00: And by franchise, I mean committing to a territory, a region, something like that.
• 5:32
  SPEAKER_00: Early in my career, I was too opportunistic and would swap territories inside a company, roles inside a company, and even companies a little bit too quickly, right?
• 5:45
  SPEAKER_00: I would get distracted.
• 5:46
  SPEAKER_00: I would say, well, I'm selling over here, it's kind of harder than I thought it would be.
• 5:50
  SPEAKER_00: There's a territory opening up over there, I'm sure that's gonna be easier.
• 5:52
  SPEAKER_00: I'm gonna go and get that one, right?
• 5:54
  SPEAKER_00: Or I went from being a territory guy to a major account guy, whatever it was, right?
• 5:58
  SPEAKER_00: I was I was chopping and changing a little bit too much without much real thought behind it, except it just seemed better.
• 6:04
  SPEAKER_00: It seemed better, it seemed bigger, there was a bump in OTE that was going on, something like that, right?
• 6:10
  SPEAKER_00: And at the time, I bet myself that if I made those changes, I would get into the new accounts that I would be charged with in the new roles that I had.
• 6:21
  SPEAKER_00: It worked then pretty well because it was easier to do then.
• 6:25
  SPEAKER_00: And I don't believe that strategy really works all that well right now.
• 6:29
  SPEAKER_00: As you all know, it is really, really hard to get attention of people who don't know you and don't know your company.
• 6:37
  SPEAKER_00: You know, I know someone who really built a great franchise selling just to state and local government in New York City, right?
• 6:46
  SPEAKER_00: And spent many, many years doing that, building relationships, working with partners, doing the whole thing to say I'm in this for the long term.
• 6:55
  SPEAKER_00: Even though state and local government might not be that sexy, and I have no doubt that person had the chance to move to supposedly much sexier roles.
• 7:04
  SPEAKER_00: They stuck with what they were doing because they knew they built something that had longevity around it.
• 7:09
  SPEAKER_00: I remember back in the day, I once interviewed a salesperson, and what I was looking for was a much bigger regional role.
• 7:15
  SPEAKER_00: And this person was based in Omaha, Nebraska.
• 7:18
  SPEAKER_00: And in talking with them, what I realized was that sales rep and that SE that he was working with had decided that they were going to be the go-to people in Omaha, Nebraska.
• 7:29
  SPEAKER_00: They would just know every company, every decision maker, every team in every large company, every medium company in Omaha, and go out there and really treat that as their business and know that whatever the hot thing at the time was, they could all always move that little franchise they were building from vendor to vendor.
• 7:48
  SPEAKER_00: So I would make the commitment, right?
• 7:50
  SPEAKER_00: I would made the commitment.
• 7:51
  SPEAKER_00: I would say, you know, I'm gonna network, I'm gonna build things, not just for the opportunities that I might get right now, but for building things for the long term.
• 7:59
  SPEAKER_00: You know, these people that we work with, they're building careers.
• 8:02
  SPEAKER_00: And if I was doing it right now, I would say I'm gonna build my franchise in this area and get to know all these people and build relationships and build trust with them so that wherever, whichever vendor I end up at, I can take that franchise with me.
• 8:17
  SPEAKER_00: So that's way number two.
• 8:18
  SPEAKER_00: Number three, I think I would do differently, is I would look for waves first and not companies first.
• 8:27
  SPEAKER_00: So, what does that mean?
• 8:28
  SPEAKER_00: My biggest mistake when joining some startups is not thinking about the waves that exist or even don't exist that they're playing in.
• 8:38
  SPEAKER_00: You know, it's so much easier to join a company as part of a much bigger movement that's happening, as opposed to trying to create the movement that's happening.
• 8:47
  SPEAKER_00: It's really hard to do.
• 8:49
  SPEAKER_00: So, for example, recently, now I'm sure there's a whole bunch of things that went into the success of Snowflake, but one thing for sure is they did not create the wave of moving data from on-prem into the cloud.
• 9:02
  SPEAKER_00: That wave was happening.
• 9:04
  SPEAKER_00: They just figured out a way to do it that was very compelling, very elegant, and worked really well.
• 9:10
  SPEAKER_00: And they just rode that wave very well.
• 9:12
  SPEAKER_00: You know, great talent over there, good people, good product, right?
• 9:15
  SPEAKER_00: Don't get me wrong, but that big on-prem decloud wave was happening.
• 9:20
  SPEAKER_00: They realized that, jumped on it, and made it work, right?
• 9:23
  SPEAKER_00: If you weren't writing a way, a big wave like that, it's really hard to do, right?
• 9:28
  SPEAKER_00: You you're trying to convince people that there's a bigger thing going on, which they may not agree with, probably won't agree with.
• 9:34
  SPEAKER_00: And you have to try and create this thing yourself.
• 9:37
  SPEAKER_00: And if your product isn't amazingly differentiated and really, really compelling, it's hard to do.
• 9:43
  SPEAKER_00: So, two ways to do that.
• 9:45
  SPEAKER_00: Firstly, just generally in the industry, I would listen about what's going on, right?
• 9:50
  SPEAKER_00: I would listen to what is going on, what the buzz is all about, what people are talking about in the Snowflake example, you know, you know, that's not new, right?
• 9:59
  SPEAKER_00: People start moving from on-prem to cloud, I don't know, eight, 10 years ago, maybe, as the waves start to really gather momentum, right?
• 10:06
  SPEAKER_00: So I would start listening out for these things that you just get a sense for.
• 10:10
  SPEAKER_00: The second thing I would do is I would talk to customers, you know, my friendlies that I that I know.
• 10:16
  SPEAKER_00: And socially or informally, I'd be asking them, you know, what are they looking at?
• 10:20
  SPEAKER_00: What are the big things they're looking to tackle?
• 10:22
  SPEAKER_00: What are they seeing changing in their world or in the IT world that might have an impact on information security, on cybersecurity?
• 10:31
  SPEAKER_00: An example of that is a few episodes ago, I interviewed Mike Baker.
• 10:36
  SPEAKER_00: And Mike is currently the CRO at No Name Security.
• 10:40
  SPEAKER_00: And Mike talked about on the episode how two of his moves, one to Armus and one to No Name, were based on just hearing from his customers what they were thinking about and what they were struggling with.
• 10:53
  SPEAKER_00: Right?
• 10:54
  SPEAKER_00: He was asking them and listening for, you know, forget what he was selling at the time.
• 10:58
  SPEAKER_00: He was looking for that next thing always, that that big thing that was happening, the wave that was was going on to go and latch onto.
• 11:06
  SPEAKER_00: So you can definitely do it with friendlies out there as well.
• 11:09
  SPEAKER_00: So, and then once you see the wave, then you can figure out which of the companies that are most likely to succeed, ride that wave the best and have the most momentum, and then join those ones.
• 11:21
  SPEAKER_00: The fourth thing I would do is I would not work for unbuzzworthy CEOs or founders.
• 11:30
  unknown: Right?
• 11:31
  SPEAKER_00: I know that's probably not a word, but uh go with me on that, right?
• 11:34
  SPEAKER_00: I have definitely joined companies despite being underwhelmed with the CEO, right?
• 11:40
  SPEAKER_00: I've known people at the company, I've known the sales leader.
• 11:44
  SPEAKER_00: You get be able to meet with the CEO as part of the process and come away thinking, you know, I'd probably still join, even though that person did not blow me away, right?
• 11:54
  SPEAKER_00: And I think that was a mistake on my part.
• 11:56
  SPEAKER_00: And for two reasons.
• 11:58
  SPEAKER_00: One is, as we know, if you've been at startups, it's hard, right?
• 12:03
  SPEAKER_00: This it's not the easiest way to make a few bucks here and there, right?
• 12:07
  SPEAKER_00: And having a truly inspirational, dynamic leader can really make the difference as we're looking as we're looking to help the team, help the company overcome roadblocks and break through and really make a difference.
• 12:20
  SPEAKER_00: Someone who's very passive and might be smart as anything and just a great person, but not be inspirational and buzzworthy is perhaps not the right person to work for.
• 12:31
  SPEAKER_00: The second reason, and perhaps the most importantly for sales, is buzzworthy CEOs get media attention.
• 12:39
  SPEAKER_00: They get attention from media, they get attention for funding, and they get attention from prospects.
• 12:45
  SPEAKER_00: People want to meet them, people want quotes from them, people want to attach their name to that buzzworthy CEOs.
• 12:55
  SPEAKER_00: A couple of episodes ago, I talked with Mike Rogers about our shared time at Ionic Security.
• 13:01
  SPEAKER_00: At Ionic, our founder was someone called Adam Getty.
• 13:05
  SPEAKER_00: And Adam at the time was pretty young, he was in his late 20s, but he had that thing, right?
• 13:11
  SPEAKER_00: People, what he taught, people listened.
• 13:14
  SPEAKER_00: He got funding.
• 13:16
  SPEAKER_00: He had people, he had very sophisticated VCs falling about trying to fund what he was doing.
• 13:21
  SPEAKER_00: Because when you hear how he talked about what he was trying to achieve and why it was so important and the big idea, it was really compelling, right?
• 13:29
  SPEAKER_00: Really compelling and word spread.
• 13:31
  SPEAKER_00: You know, he was talking to CISOs at some of the biggest companies in the world who wanted to directly interact with Adam and get to know him and see what he was all about.
• 13:41
  SPEAKER_00: And for us as sellers, that's important.
• 13:44
  SPEAKER_00: And then, of course, you know, the press picks up on it.
• 13:46
  SPEAKER_00: And if you got someone who is compelling like that, they want quotes from that person.
• 13:50
  SPEAKER_00: They want to get them on video, right?
• 13:52
  SPEAKER_00: Adam had all that in spades.
• 13:54
  SPEAKER_00: It was really, really interesting to see.
• 13:56
  SPEAKER_00: More recently, you know, there's lots of reasons again behind CrowdStrike success, but I would say that one of them is that George Kurtz was the CEO.
• 14:05
  SPEAKER_00: There's a person who'd been in cybersecurity for a long time.
• 14:08
  SPEAKER_00: He was part of the founding team that built and ran Founstone, which had a huge and great reputation back in the early 2000s.
• 14:16
  SPEAKER_00: He was known in the community.
• 14:18
  SPEAKER_00: And when he talks, he's a very compelling speaker, right?
• 14:21
  SPEAKER_00: This buzz about George when he talks, there's something about him.
• 14:25
  SPEAKER_00: People listen.
• 14:25
  SPEAKER_00: Same with Kevin Mandia, right?
• 14:28
  SPEAKER_00: Back in the day before Fire Eye Amandian became one, it was his business.
• 14:32
  SPEAKER_00: And they were winning business because of Kevin.
• 14:35
  SPEAKER_00: He's a very direct, very candid speaker.
• 14:38
  SPEAKER_00: Comes across as just completely credible when you hear him talk.
• 14:42
  SPEAKER_00: So there's examples of people that if I was at a startup and they were my CEO, they'd be getting the buzz, they'd be getting the things that I would want from that person that's going to help me in my motions to sell.
• 14:55
  SPEAKER_00: You know, you can still survive and succeed without that, but it makes it easier, right?
• 15:00
  SPEAKER_00: When you're trying to rise above the noise out there and try and have something that people latch onto that want to be, they want to be part of, having a buzzworthy CEO can be really influential.
• 15:12
  SPEAKER_00: And I would have avoided a couple of duds that I went to if I'd had that as one of my filters.
• 15:18
  SPEAKER_00: Now, as I would say, these are none of these are hard and fast rules.
• 15:21
  SPEAKER_00: I think there's things to think about and things that I would think about doing differently based on those.
• 15:27
  SPEAKER_00: So what were they?
• 15:28
  SPEAKER_00: First of all, really commit to going all in on cybersecurity.
• 15:32
  SPEAKER_00: Secondly, look to build a franchise rather than just build a pipeline for today.
• 15:37
  SPEAKER_00: I would look to join a WAVE, not a company, first.
• 15:40
  SPEAKER_00: And then I would look for a truly inspirational and buzzworthy leader to join.
• 15:45
  SPEAKER_00: And I believe in my career, if I was starting now, those things would be impact things for me that I'd be looking for for my next move.