Latest / Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth / 127: 2 questions to ask the CEO/founder before joining a cyber security startup

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127: 2 questions to ask the CEO/founder before joining a cyber security startup · Cyber Go-To-Market Talk: The Cybersecurity Podcast About Cyber Sales, Marketing & Revenue Growth

• 0:32
  SPEAKER_00: You are considering joining a startup, are excited about what you've heard so far, and now get to meet the founder or the CEO.
• 0:40
  SPEAKER_00: In this episode, I'll give you two important questions to ask them.
• 0:54
  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.
• 1:03
  SPEAKER_00: Sales Bluebird gives you tips, tricks, experiences, examples, inspiration, and ideas from people who've been doing this for many years and at many companies.
• 1:12
  SPEAKER_00: I am your host, Andrew Monahan.
• 1:15
  SPEAKER_00: So at a startup, the founder has a big, big impact on everything to do with the company, the success of the company, ultimately, the tone, the character, the culture, the messaging, the vision, the attitude, how they're viewed by prospects, how loud they are, how quiet they are.
• 1:35
  SPEAKER_00: Their role in the company has is wide-ranging and it goes deep.
• 1:41
  SPEAKER_00: You know, it's not at all uncommon for sales teams or marketing teams to be doing work and have the founder, CEO come in and say, we're doing it all wrong.
• 1:50
  SPEAKER_00: We need to change this up, do that, do it my way, do it my way, do it my way, right?
• 1:55
  SPEAKER_00: Not at all uncommon for that to happen.
• 1:57
  SPEAKER_00: So this person who is the founder, whose life is all about this startup, has an unbelievable role in how things are going to pan out, both for the company, but also for you as an individual who's thinking about joining the sales teams.
• 2:11
  SPEAKER_00: Unfortunately, many people are attracted by the promise of untold riches and IPOs and exits, unbelievable valuations that they'll get by joining this rocket ship early, right?
• 2:25
  SPEAKER_00: This the rocket ship is the phrase.
• 2:26
  SPEAKER_00: We want rock stars, and we and we're a rocket ship, is what we will talk about.
• 2:30
  SPEAKER_00: I know this because I've done it.
• 2:32
  SPEAKER_00: I've joined three startups, and you know, two of them very small, one a little bit bigger.
• 2:37
  SPEAKER_00: And I've experienced that.
• 2:38
  SPEAKER_00: I've seen the role this person can play and quite what it means for how things play out.
• 2:43
  SPEAKER_00: You know, when we meet with the founder, it's a unique opportunity to get a lens into the true culture and true direction of the company.
• 2:53
  SPEAKER_00: You know, this person does dictate a lot, their attitude, their wherewithal, their credibility, their gravitas, their whole thing about how they they work and work with their teams is what we get after.
• 3:05
  SPEAKER_00: Unfortunately, many of us don't use the opportunity all that well because we don't have the killer questions to ask them.
• 3:12
  SPEAKER_00: It becomes a little bit of a discussion that's not too in-depth sometimes and doesn't really get to the heart and soul about what you really want to ask them.
• 3:20
  SPEAKER_00: And sometimes, you know, if you've got a visionary founder, they're going to go off and tell you all sorts of amazing things that can blow you away if you're not used to having that type of person and don't have something to fall back on, which is some good questions to ask them.
• 3:34
  SPEAKER_00: You know, and without these questions, you lose control over what the founders tell you.
• 3:38
  SPEAKER_00: Founders are that visionary and compelling person, so you're more likely to be swayed by what they're telling you.
• 3:43
  SPEAKER_00: And you don't always know exactly where to dig, right?
• 3:46
  SPEAKER_00: In the world of very superficial questions, there's some that we need to go deep on.
• 3:50
  SPEAKER_00: And that's what these two questions give you.
• 3:53
  SPEAKER_00: They can help you easily decide whether you should change your life, sacrifice whatever path you were on, change your path, potentially put at risk a bunch of things about your career by joining this startup for the promise of this life-changing changing experience.
• 4:06
  SPEAKER_00: So here's what to look for when you have that meeting with the founder or the CEO.
• 4:11
  SPEAKER_00: First one, ask the founder what business problem they solve for their ideal customer profile.
• 4:18
  SPEAKER_00: What's the business problem that is solved by the product, by the company, for their ICP?
• 4:25
  SPEAKER_00: This is where the rubber meets the road, right?
• 4:27
  SPEAKER_00: This is probably the most important thing when thinking about what our chances of success are with this company going forward.
• 4:34
  SPEAKER_00: Without clarity around this, frankly, we're all wasting our time.
• 4:40
  SPEAKER_00: Right?
• 4:40
  SPEAKER_00: Confusion is not good if we can't really understand what we're doing for these prospects.
• 4:46
  SPEAKER_00: A founder who will be tough to work with will go on, they'll answer the question about the problem that we solve by telling us all about the product, right?
• 4:56
  SPEAKER_00: They'll wax lyrical about the product that he and his team have built, how amazing it is, how groundbreaking it is, how stupid people would be if they don't buy it.
• 5:06
  SPEAKER_00: It solves world peace and hunger at the same time, etc.
• 5:10
  SPEAKER_00: etc.
• 5:10
  SPEAKER_00: etc.
• 5:11
  SPEAKER_00: Right.
• 5:11
  SPEAKER_00: That's how they'll answer the question.
• 5:13
  SPEAKER_00: They'll answer it in technical terms, not in business terms.
• 5:18
  unknown: Right?
• 5:18
  SPEAKER_00: They'll get into the weeds very quickly.
• 5:21
  SPEAKER_00: And they won't be thinking, they won't be telling you about the real outcomes that you deliver for the prospect.
• 5:28
  SPEAKER_00: And frankly, what they'll do is go way over their skis on what the product is right now.
• 5:33
  SPEAKER_00: And rather than talking about a vision, they'll talk about what we're able to do, what we're able to do, what we're able to do, what this can do right now.
• 5:40
  SPEAKER_00: And frankly, you know, they get over their skis, and it's not the reality of what the product can actually deliver right now.
• 5:46
  SPEAKER_00: So that's what the that's what happens when you have someone who doesn't answer that question well.
• 5:50
  SPEAKER_00: A founder you want to work with will actually answer it very clearly.
• 5:55
  unknown: Right?
• 5:55
  SPEAKER_00: They'll be crisp in their answer.
• 5:57
  SPEAKER_00: It will be obvious that they've answered this question for business prospects many times before because of how they answer it.
• 6:05
  SPEAKER_00: They'll answer it by truly answering the what is the problem they solve without talking about their product, right?
• 6:09
  SPEAKER_00: They'll they'll actually go to the question you ask them.
• 6:12
  SPEAKER_00: These are the business problems that our ICP has, and these are the ones that we can solve, and this is how we can solve them.
• 6:18
  SPEAKER_00: But they'll also be humble enough and aware of the market enough to know that things change.
• 6:22
  SPEAKER_00: And you know that's where things are right now, but they might even drop in, you know, with this challenges, right?
• 6:28
  SPEAKER_00: We've got this competitor, that competitor, different approach, status quo, whatever it might be, when people are thinking about the problems and how they solve them.
• 6:35
  SPEAKER_00: Or maybe they may be humble enough to recognize that not everyone wants to solve the problem, right?
• 6:40
  SPEAKER_00: They'll they'll categorize it as saying there's a certain, you know, of the total graspable market, there's only a certain portion that we can really tackle right now, and that's this one over here.
• 6:50
  SPEAKER_00: This is a founder who answers like this, who's been doing this with prospects for a while.
• 6:55
  SPEAKER_00: They've listened to responses, key question, key word there.
• 6:58
  SPEAKER_00: They've listened to responses from prospects as they've gone out early and done founder-led selling, and they've adjusted their explanation, they've adjusted the words they use.
• 7:08
  SPEAKER_00: So by the time that you come along, you get a very, very compelling answer to that question.
• 7:14
  SPEAKER_00: So that's the first question.
• 7:15
  SPEAKER_00: The second question is I would ask the founder how they do it differently to everyone else, and why a security leader would care about that.
• 7:26
  SPEAKER_00: Okay, so why would they why do they how do they do it differently and why would anyone care that they do it differently that way?
• 7:32
  SPEAKER_00: You know, too often we're bamboozled by the amazing tech and how amazing it is, and all the great things it does, and it's like changed the world and all the rest of it.
• 7:42
  SPEAKER_00: And that's that, you know, maybe in the eye of the founder, that's exactly what they're trying to do, other the outcomes that they want.
• 7:49
  SPEAKER_00: Um, because they're neck deep in this, right?
• 7:51
  SPEAKER_00: They're in day-to-day, they're thinking very tactical, very small things on a day-to-day, week-by-week basis.
• 7:58
  SPEAKER_00: Um, and they can come across as knowledgeable and passionate, but they get way down into the weeds and try and give very detailed explanations of something that should be explained very clearly.
• 8:08
  SPEAKER_00: You know, this is a classic example where we need to put ourselves in the shoes of a security leader and challenge the founder to explain why I should care about that.
• 8:19
  SPEAKER_00: So I would actually add in, did I even understand what they were talking about?
• 8:22
  SPEAKER_00: Did they answer the question weigh down the weeds so much that really only an analyst or an engineer or a first-level manager in uh in a security organization is gonna care?
• 8:34
  SPEAKER_00: That's one red flag.
• 8:36
  SPEAKER_00: Um, and and then secondly, if they're not able to then translate that into business outcomes, that's gonna be a red flag for me as well.
• 8:43
  SPEAKER_00: But putting ourselves in the shoes of the CISO, the security leader, you know, can I clearly understand the big impact this is gonna have on me and why it's so different to everyone else, right?
• 8:55
  SPEAKER_00: And if it's not in the terms of, you know, this approach leads to a vastly different outcome, it's gonna be tough for many people to change, right?
• 9:03
  SPEAKER_00: You know, the classic thing is when they're changing technologies inside IT organizations and security organizations, they're looking for big improvements, not small improvements, right?
• 9:11
  SPEAKER_00: You don't make big investments and big transformations trying to get small incremental increases.
• 9:16
  SPEAKER_00: They're looking for, is this gonna be 5x better than what we have right now?
• 9:19
  SPEAKER_00: Is it gonna be 5x better than the company we leaked at last week?
• 9:23
  SPEAKER_00: Right?
• 9:23
  SPEAKER_00: Is this approach so unique, so different that it's gonna have a big impact rather than someone saying, well, we've got a little widget that does things a little bit differently and it's you know two milliseconds faster and things like that?
• 9:34
  SPEAKER_00: That's that's not the answer we really want to hear.
• 9:36
  SPEAKER_00: You know, a weak founder hasn't worked this out yet, right?
• 9:39
  SPEAKER_00: When they answer the question, they they don't hit the right tone, they don't explain it clearly enough, they make it more complicated than it needs to be, they don't have examples from real prospects, right?
• 9:49
  SPEAKER_00: And they haven't probably even tried to do this effectively with real prospects.
• 9:54
  SPEAKER_00: And that to me is a red flag.
• 9:55
  SPEAKER_00: A great founder will completely get this, right?
• 9:59
  SPEAKER_00: They'll just naturally or from practice be able to explain the differentiation as if you're a security leader in words that everyone can understand that can be clearly attached to value and impact and big changes as well.
• 10:14
  SPEAKER_00: Right.
• 10:15
  SPEAKER_00: And they've probably got great examples of where they've done this already with other customers.
• 10:19
  SPEAKER_00: And they'll be able to get as far as saying, you know, here is the measurement.
• 10:23
  SPEAKER_00: You know, when we did it this much better, this was the measurement and this was the business impact.
• 10:28
  SPEAKER_00: And they might even be able to say that, you know, the the person, the CISO or the VP of security actually had a you know big, big positive gain internally at their organization when they adopted the technology.
• 10:39
  SPEAKER_00: Those are the two questions I would make sure you ask them and really dig deep, right?
• 10:43
  SPEAKER_00: Don't get carried away in the hype, the big flowery language and the big claims and all the rest of it.
• 10:47
  SPEAKER_00: You know, go specific on these two things because it's going to give you an idea how they respond to your questions and whether they can give you good answers or compelling answers to the questions, whether they're the right person that you want to work for.
• 10:59
  SPEAKER_00: The final thing I would say about this is ask for a specific time to cover this on its own.
• 11:05
  SPEAKER_00: Right?
• 11:06
  SPEAKER_00: This this type of thing is that important.
• 11:08
  SPEAKER_00: Don't have it be tacked on to an hour-long interview where it's five minutes of the interview, right?
• 11:13
  SPEAKER_00: Maybe have ask for a specific session for just half an hour, maybe, around these types of questions to really make sure that you understand what's going on with them.
• 11:22
  SPEAKER_00: And then come on with these specific questions to dig deep.
• 11:25
  SPEAKER_00: Be ready to redirect them away from whichever path they want to go down and bring them back to what uh what you want to talk about.
• 11:33
  SPEAKER_00: Because how these founders explain these topics will give you a good indication of how they've been thinking about their company, how they talk about their product, how they run things internally, how many times they've spoken with prospects that are senior enough that it matters, and how ready they really are to work with a great sales team to be successful.