Latest / Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth / 161: 5 ways to reduce the chaos in startup selling

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161: 5 ways to reduce the chaos in startup selling · Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth

• 0:32
  SPEAKER_00: Sometimes when the business is not drawing, deals are not closing, or not closing fast enough, first meeting conversion rates are low.
• 0:40
  SPEAKER_00: It is not a product market fit problem, a product problem, a tools problem, or anything like that.
• 0:46
  SPEAKER_00: Sometimes it's a consistency problem.
• 0:48
  SPEAKER_00: Find out what that means in this episode.
• 1:01
  SPEAKER_00: Welcome to the Sales Bluebird podcast, which exists because at B2B startups it's hard to get consistent traction and scale the sales team.
• 1:09
  SPEAKER_00: Sales Bluebird gives you tips, tricks, experiences, examples, and ideas from people who know a thing or ten about selling and building great cybersecurity companies.
• 1:18
  SPEAKER_00: I am your host, Andrew Monahan, and today it is a solo episode with yours truly, and we're talking about consistency and what that really means.
• 1:25
  SPEAKER_00: I'm going to use an example, so bear with me on this.
• 1:28
  SPEAKER_00: Imagine that you're having a group meeting or a group get together, and the get together was in New York, but everyone in the group and the team was based in San Francisco.
• 1:40
  SPEAKER_00: And rather than just saying, hey, let's all just go there, you said, let's all go there, but you know, everyone make their own way, figure out their way of getting there.
• 1:47
  SPEAKER_00: Whatever you like to do to travel, whatever way you want to take this, why don't you go do that?
• 1:52
  SPEAKER_00: And everyone goes off choosing their favorite way to travel from San Francisco to New York.
• 1:58
  SPEAKER_00: And what happens, of course, is that you've got someone who likes to hike and they put on their boots and away to go hiking.
• 2:04
  SPEAKER_00: And you got some people who are bike nuts and they uh they put the liker on and the helmets and off they go on their bikes.
• 2:11
  SPEAKER_00: You get some that are hardly nuts and they go, oh, let's uh let's not put our helmets on, let's just uh drive over there.
• 2:17
  SPEAKER_00: We'll go some certain route that's there, maybe through North Dakota or South Dakota and all the hell through there through Sturgis.
• 2:22
  SPEAKER_00: You got people that like to drive, and they got some fancy car, you want to drive their car.
• 2:28
  SPEAKER_00: You got the frequent flyer people who've got a ton of miles who's like, oh, I'm gonna get there on my miles.
• 2:32
  SPEAKER_00: Like I know how to do that.
• 2:33
  SPEAKER_00: I've got United Miles out of SFO.
• 2:35
  SPEAKER_00: It'll get me right into Newark and I can get there quickly, and it's gonna be perfect.
• 2:39
  SPEAKER_00: I'll get an upgrade.
• 2:40
  SPEAKER_00: That's my way of going.
• 2:41
  SPEAKER_00: And what happens, of course, is everyone just picks what they're comfortable with, what their favorite way of traveling is.
• 2:47
  SPEAKER_00: The trouble is that what will happen is everyone will get there at different times, right?
• 2:53
  SPEAKER_00: And they'll have different successes.
• 2:54
  SPEAKER_00: Some may never get there, right?
• 2:55
  SPEAKER_00: The people that are hiking might get as far as Yosemite and go, ah, let's just hang out here for a while because it's kind of cool and it's a it's a great view.
• 3:03
  SPEAKER_00: And my feet again blisters, right?
• 3:05
  SPEAKER_00: And also, you know, when you're thinking about it, when you're doing the debrief afterwards, you're not really gonna learn very much, right?
• 3:10
  SPEAKER_00: You're gonna sit there and go, well, how did everyone get here?
• 3:13
  SPEAKER_00: And when you realize is that half the team's not there.
• 3:15
  SPEAKER_00: And uh the other thing you realize is that you know, trying to draw comparisons between someone who is on their bike versus someone who flew first class on United, it's so completely different.
• 3:27
  SPEAKER_00: It's hard to really draw conclusions on what might be the best way to get there.
• 3:32
  SPEAKER_00: And if you think about it, that's what happens a lot in early stage sales teams.
• 3:36
  SPEAKER_00: You know, there is that element of figuring things out.
• 3:38
  SPEAKER_00: There is that element of we got a small team here, might be three or four sellers, let's say.
• 3:43
  SPEAKER_00: And uh we don't have things perfect, but you know, that we've hired the right people and we're gonna figure this out along the way.
• 3:49
  SPEAKER_00: And they they go there knowing they're gonna learn, right?
• 3:52
  SPEAKER_00: The trouble is, is if you just stop there and say, you know, I trust these people, they'll figure it out, they bring their own things, their BYO, BYO methodology, BYO positioning, BYO qualification, BYO discovery, all the things that in their experience has worked for them in the past is what they will do.
• 4:12
  SPEAKER_00: And it may well be, in fact, is often very different to the person who has the territory one territory over, right?
• 4:19
  SPEAKER_00: If you've got a team, let's say you've got a leader who sort of carries a bag a little bit, and you've got an east and a west or an east, middle, and west, you know, one territory over, people are doing things completely differently.
• 4:30
  SPEAKER_00: And that causes problems, right?
• 4:31
  SPEAKER_00: Because what you're in in that stage is we're in the stage of learning.
• 4:35
  SPEAKER_00: We're in the stage of drawing conclusions and figuring out what is the repeatable sales process we need to get to to scale this thing.
• 4:43
  SPEAKER_00: And if everyone is doing their different things, then it's really hard to draw the right conclusions or interesting or meaningful conclusions to say this is the way we need to build the playbook and go and scale this business.
• 4:56
  SPEAKER_00: But let's go back to our analogy, right?
• 4:58
  SPEAKER_00: What if there was someone in the team or someone you knew who actually had done that trip from SFO to United or to New York so many times, they just knew the best way to go.
• 5:08
  SPEAKER_00: They actually knew to avoid flying United because that plane gets delayed or canceled all the time.
• 5:13
  SPEAKER_00: And actually, the way to do it, if you set out early enough, is to go on the train, right?
• 5:16
  SPEAKER_00: And uh you get to do work on the train and it's an experience because you bond and all the rest of it, right?
• 5:20
  SPEAKER_00: But basically you got someone who's got some experience of doing that, who sits the team down and said, listen, we think we've got the best way of getting there, which might be the train, let's say.
• 5:30
  SPEAKER_00: Now there's two or three different routes to get there at different speeds, you can choose what you're comfortable with.
• 5:34
  SPEAKER_00: But the the most productive and cost-effective way is that we all get the train.
• 5:39
  SPEAKER_00: And then when you get to New York and you're sitting there, everyone is there, and you got comparisons, right?
• 5:45
  SPEAKER_00: You can compare the seats on the, by the way, I have no idea if there's such a thing as a north route and a south route on the train.
• 5:50
  SPEAKER_00: Maybe there's only one, I don't know.
• 5:51
  SPEAKER_00: But you know, you're comparing the seats on the north route versus the south route.
• 5:55
  SPEAKER_00: You're comparing the views, going through the Rockies on the North Route, going through, I don't know, Arizona and the South Route, you know, different views, all the rest of it.
• 6:04
  SPEAKER_00: You got some comparison points that are common between the people who are trying to get there, right?
• 6:09
  SPEAKER_00: And what you have at that point when you get to New York is the ability to learn, draw conclusions, have a shared experience, everyone's there, and you're having a good time.
• 6:17
  SPEAKER_00: To make it a bit more real, like one of um someone I know, we'll call him Dan, mostly because that's his name.
• 6:24
  SPEAKER_00: So Dan started a company a couple of years ago, three years ago, first person in the go-to-market team.
• 6:30
  SPEAKER_00: And he set his stall out early on.
• 6:32
  SPEAKER_00: He said, you know, we're gonna do this together, we're gonna have a common way of working.
• 6:35
  SPEAKER_00: And one of his great skill sets is that he can sell and build a team, but also he knows how to on the fly almost create the process that goes with it.
• 6:45
  SPEAKER_00: So when he added a new team member on, there were some basic foundational tools already in place that had been iterated on again and again.
• 6:52
  SPEAKER_00: And uh that person walking in wasn't met with blank stares or, hey, let's just go and chat about you know how to sell for a while, right?
• 6:59
  SPEAKER_00: There was actually some frameworks and some tools in place.
• 7:02
  SPEAKER_00: And you know, and Dan scaled that team from three at the start, or oh, it's him at the start, and then he added a couple of reps pretty quickly up to 30 inside 18 months, right?
• 7:10
  SPEAKER_00: So there are ways to do this, is the good news, right?
• 7:13
  SPEAKER_00: You don't need to lose the spirit of experimentation and the idea that you are trying to figure things out as you go along by being in a startup, right?
• 7:23
  SPEAKER_00: You don't have to throw it all out and just let chaos reign.
• 7:26
  SPEAKER_00: There are ways to bring some order to the chaos.
• 7:29
  SPEAKER_00: And I've got five ways for you to think about how to do that if you're facing this problem right now.
• 7:34
  SPEAKER_00: The first one is I would invest right now, if you're in this boat, in a conversation intelligence tool.
• 7:41
  SPEAKER_00: This is the gongs, the chorus.
• 7:42
  SPEAKER_00: I think Sales Loft have one in their tool.
• 7:45
  SPEAKER_00: I'm sure there's a whole bunch now, right?
• 7:47
  SPEAKER_00: So why so early, right?
• 7:48
  SPEAKER_00: So I think that the common view is conversation intelligence tools are to coach reps, right?
• 7:54
  SPEAKER_00: And sure, they're good at that.
• 7:56
  SPEAKER_00: But what it gives you in early stage startup is it gives you the ability to go back and listen carefully to what was said by both the selling team but also the prospect team.
• 8:07
  SPEAKER_00: You can figure out, you know, we said this, that was our new way of describing what we do.
• 8:12
  SPEAKER_00: How did it hit home across all the calls last week?
• 8:14
  SPEAKER_00: And you go in quickly to that point in the conversation.
• 8:17
  SPEAKER_00: Let's say you're a terrible messaging company and you said your phrase was, I don't know, we we do encryption AI, let's say, I don't know, making that up.
• 8:24
  SPEAKER_00: You can go in and search for every time in the last week there was a call where encryption AI was said.
• 8:31
  SPEAKER_00: Look at that snippet and see what the prospect did or said afterwards, right?
• 8:35
  SPEAKER_00: So, in terms of analyzing what's working, not working across multiple calls, thinking about you know, snippeting requests from prospects and giving it to the product team to say, you know, we had this request come through, uh, you know, give us your advice on whether it's something we want to do or not do, or how to handle this question if it comes up again, if we're not gonna do it.
• 8:53
  SPEAKER_00: This is uh it's so valuable.
• 8:54
  SPEAKER_00: And I think the temptation is to push off the investment in CI.
• 8:58
  SPEAKER_00: I would do it right at the start.
• 8:59
  SPEAKER_00: I would get in there as early as you can possibly afford to do it.
• 9:02
  SPEAKER_00: And they're not expensive to do.
• 9:04
  SPEAKER_00: And in fact, if you're gonna invest in something like sales loft, you get one with it.
• 9:07
  SPEAKER_00: So there's no reason not to do that.
• 9:09
  SPEAKER_00: The second thing I would do is kind of like I was saying with Dan, build some common frameworks.
• 9:14
  SPEAKER_00: You know, you don't need to go to all degrees and figure out the 15 different templates you need to build about all the different sales situations you get into.
• 9:21
  SPEAKER_00: But there's some foundations, right?
• 9:23
  SPEAKER_00: There's got to be a way you describe in a common manner what the company does, what the product does, the vision.
• 9:29
  SPEAKER_00: There's got to be a way to do discovery that is broadly the same across everyone in the team.
• 9:34
  SPEAKER_00: When someone asks you the uh differentiation, you know, how are you different to you know, major competitor, you've got a set way of doing it, right?
• 9:41
  SPEAKER_00: And you build out these simple frameworks.
• 9:43
  SPEAKER_00: And what you do when you do that is you get everyone the same freeway, but it's okay to be in slightly different lanes.
• 9:49
  SPEAKER_00: So what does that mean?
• 9:50
  SPEAKER_00: Yeah, you don't want to script things out for people, right?
• 9:53
  SPEAKER_00: Any seller worth of salt will sound stupid and not want to sound stupid.
• 9:57
  SPEAKER_00: But what you can do is say, look, here's the direction we want to go in in this, here's the points we need to make.
• 10:02
  SPEAKER_00: Now put it in your style, put it in your voice so that it sounds credible when you say it.
• 10:06
  SPEAKER_00: Number three, and this is so important, hiring the right people.
• 10:09
  SPEAKER_00: You know, you want that early team to be curious learners, right?
• 10:14
  SPEAKER_00: They've got to go in there knowing we don't know everything yet.
• 10:16
  SPEAKER_00: We've got an idea that this is the way to do things, but I'm perfectly able to listen to what happens and be aware of how things are going at a call to know whether our latest idea about how to describe what we do is working or not, for example.
• 10:29
  SPEAKER_00: Right.
• 10:29
  SPEAKER_00: So they've got to be curious learners.
• 10:31
  SPEAKER_00: They'd be curious to ask a lot of questions and really get into problems with the prospect because sometimes they're not completely defined as well as we'd like, and learn about what they're hearing back and be able to understand it and adapt on the fly.
• 10:43
  SPEAKER_00: So hiring the right people is so important.
• 10:45
  SPEAKER_00: Fourthly, I would say is internal to the team, talk a lot, right?
• 10:50
  SPEAKER_00: Literally talk a lot.
• 10:51
  SPEAKER_00: This should be in this world where we're all remote, or most of us are, and certainly in an early stage, you you've probably got people, you know, if you got a couple of people, two or three people in the sales team, you'll hopefully be in different parts of the country because you're spreading people out a little bit.
• 11:04
  SPEAKER_00: But you need to engineer situations where you talk a lot.
• 11:07
  SPEAKER_00: You know, it's gotta be how do we have lunch every day, or the equivalent of that.
• 11:11
  SPEAKER_00: So we talk about what we're experiencing and things that we're hearing and ideas that we have, things like that, right?
• 11:16
  SPEAKER_00: And that's one of the things that Dan did really well.
• 11:19
  SPEAKER_00: He had multiple calls each week.
• 11:21
  SPEAKER_00: And he would actually, you know, in these calls, for example, he'd just pull up gong, or I think he had chorus, he'd pull up chorus and say, let's listen to some calls.
• 11:27
  SPEAKER_00: And, you know, he was perfectly willing to call himself out.
• 11:30
  SPEAKER_00: Yeah, I screwed that up.
• 11:31
  SPEAKER_00: I should have done this a different way.
• 11:33
  SPEAKER_00: I actually didn't understand the nuance there.
• 11:35
  SPEAKER_00: You know, it's okay to it's basically a collaboration in the team to say, what are we doing?
• 11:39
  SPEAKER_00: What are we doing well?
• 11:40
  SPEAKER_00: Examples where things aren't hitting, examples where things are, and just have that ongoing discussion in the small team so that ideas can free flow between each other.
• 11:49
  SPEAKER_00: And that's how good learning takes place.
• 11:52
  SPEAKER_00: And what is a simple idea?
• 11:53
  SPEAKER_00: You can go miles deep with uh two or three team members as you talk about how best to do something.
• 11:58
  SPEAKER_00: So talk a lot.
• 11:58
  SPEAKER_00: And the fifth one and last one in the list here is constantly iterate and update the content and the frameworks, right?
• 12:05
  SPEAKER_00: This is not an exercise in creating a PDF and saying, you know, we're good for a year on some of this stuff, right?
• 12:11
  SPEAKER_00: This is Google Doc versus PDF.
• 12:13
  SPEAKER_00: It's a case of saying we sort of know things right now, we don't know if they're perfect, and we're willing to iterate on them.
• 12:18
  SPEAKER_00: So let's keep updating what we're doing.
• 12:20
  SPEAKER_00: You know, as we get more objections, let's update the objection bank, right?
• 12:24
  SPEAKER_00: As we're thinking about new ways to describe what we do versus a competitor, let's uh update that and then let's keep notes about what we tried and what didn't work or what seemed to miss and why it missed so you can continuously learn like that.
• 12:36
  SPEAKER_00: So the concept of continuously learning and iterating on the stuff that you're creating is super important.
• 12:41
  SPEAKER_00: And I remember, you know, with Dan, he'd be on these calls and he would, you know, on the call, he would just be live updating.
• 12:47
  SPEAKER_00: Well, I think we should probably have to change this then.
• 12:49
  SPEAKER_00: Let's change how we handle it to this, let's change slide number three in the deck so it actually says this and not that.
• 12:54
  SPEAKER_00: This was a constant iteration, and uh that's what worked well.
• 12:58
  SPEAKER_00: So there's five ways to try and get more consistency, even though it's early stage, and you don't want to PDF these things, right?
• 13:07
  SPEAKER_00: This is not a one and done, it's a it's a process.
• 13:09
  SPEAKER_00: But you need the frameworks and you need frameworks to work off to be able to iterate.
• 13:14
  SPEAKER_00: The last thing you want to do is freeform this and have completely different things and have no way of trying to judge whether things are working or not.
• 13:20
  SPEAKER_00: You know, startup sales is chaotic, right?
• 13:23
  SPEAKER_00: It's the nature of that time of a company's development.
• 13:26
  SPEAKER_00: But we can't just accept the chaos and just let it rain and run rough shit over us.
• 13:31
  SPEAKER_00: We've got to make it less chaotic and predictable.
• 13:34
  SPEAKER_00: And one of the things I was thinking about, you know, in super early stages is chaos, right?
• 13:38
  SPEAKER_00: You're kind of going from finder-led sales and you've got the first person coming in to be a salesperson is chaotic.
• 13:44
  SPEAKER_00: And what you want to do as fast as possible is get to more predictable chaos, more reliable chaos.
• 13:49
  SPEAKER_00: And then you get to predictability without the chaos, and that's when you can scale the team.
• 13:54
  SPEAKER_00: So I wonder if that's a good way to think about the transitions there from chaos to predictable chaos to unpredictable.
• 13:59
  SPEAKER_00: Three different phases of early stage companies.
• 14:02
  SPEAKER_00: And you know, when we do that, our chances of getting to predictable growth increase, and we can get there faster by using common frameworks.