Big Rocks First: Prioritizing What Matters in Sales Onboarding

[00:00:00] Hey, it's Andrew. And just quickly before we start this episode, I want to tell you about one of my favorite podcasts. It's the Bare Knuckles and Brass Tax Podcast. Not only does it have a great name, it also has a really good format that's interesting. The two hosts are both named George. That's not what's interesting about it. It's that George K is on the vendor side and George A is a CISO on the customer side. And they have real conversations, sometimes with guests, about the world of vendor customer

[00:00:29] interactions. They're not afraid to call out bad behavior on both sides and talk about the weird and wonderful nature of this world of ours in cybersecurity. Recent favors of mine are the one about building trust called taking a flamethrower to FOD and buzzword mumbo jumbo, and also the one with someone who's a field CISO and advisor to startups called how security buyers think and go to market strategies for young companies. I'm not getting paid for this promo. I just really enjoy the show that two George's

[00:00:59] put on check it out. It's the Bare Knuckles and Brass Tax Podcast. Now on with this episode. The good news is that Cyber Donut has been able to hire new salespeople. The bad news is they don't have a way to ramp them fast, but they need one because they need to be delivering revenue inside six months of being on board, which when your sales cycle is round about six months, that's going to be a bit of a challenge.

[00:01:29] Unfortunately, Cyber Donut does not have anyone doing enablement to help them build a program that's going to deliver on this. So like many companies, which are earlier stage, they have to do it themselves. Now I've built numerous new hire programs for other cybersecurity companies. So stay tuned to this episode where I lay out exactly the steps and order of the steps to follow when ramping these sales new hires.

[00:01:53] I'm Andrew Monaghan and this is a cybersecurity go-to-market podcast where we tackle the question, how can Cyber Donut get to $10 million in ARR by the end of 2025? So this is a common challenge as we're growing any size of sales team, which is how do we get new hires to be productive and get producing orders, sign contracts as fast as possible.

[00:02:18] Now, bigger companies who many of us have to compete with have small armies of people doing this. They might have as many as 20 or 30 people in their enablement team. And these people are experts in adult learning, changing behavior, bringing new hires on, building a program that executes so that they can walk out of there ready to go and start making a difference. But of course, startups don't have that luxury.

[00:02:43] And frankly, what usually happens when you join a startup as a salesperson has experienced something in terms of an onboarding program, which is pretty lame. It's whatever they have time to do. Often there's a lot of shadowing, go listen to this person, go sit in their calls, read this document, things like that. And while it says better than nothing, it's not using all the best things at our disposal to help these salespeople have a chance of delivering some usually pretty aggressive goals.

[00:03:12] And for Cyber Donut and other startups, a lot is writing on this, right? The capacity plan is being built out knowing that these people are going to be delivering and are expecting that these people are going to be delivering. And it kind of needs to happen. Otherwise, the expense ratio is too high and people start asking questions.

[00:03:30] I would say the biggest aha when thinking about how to do this is when you fail to remember that you have to be very careful what you start filling new hires brains with when they're empty. Now, I know they're not really empty, but in terms of your company and the products and the solutions and the customers, they are empty, right? Essentially, you got someone walking in with a fresh mind ready to go. We have to be very intentional about what goes into that first.

[00:04:01] I don't know if you've seen a video that's been doing the rounds for many years where there's a professor at the front of a class. And he sits there or stands there in front of, I don't know, a couple of hundred people. And he's got this big jar, empty jar. I don't know what you call it, a big beaker in chemistry speak. And what he does is he's got on his desk at the front a whole bunch of different things and he fills the beaker with rocks, like big rocks. It goes until it's at the top.

[00:04:29] And he asks the class, you know, is this beaker full? And they go, yeah, it's full. And then he pulls out slightly smaller stones or rocks, right? And he feels like you can fit more in there, right? And it comes on in. And then he goes, is it full now? And they go, yes. Well, not really. He pulls out some sand and the sand goes in and that fills up even more. And it looks like it's completely packed. And he asks the class, is it full now? And they go, yeah. He goes, well, not really because then he gets water and he pours in water, right?

[00:04:58] And then you realize, I think the point of that video or what he's making to the class is that the order at which you put things in matters, right? Because if you use water at the start and then sand, you will be able to get the big rocks in. And maybe that's where the phrase, you know, where are the big rocks comes from. Now, whatever you start filling your new hire's brain with in those early days and weeks at a company is what the brain will focus on, right? It's what they will orientate everything else you tell them around.

[00:05:28] Everything they learn will be relative to that, right? And if you fill it with stuff that isn't appropriate or isn't the most impactful at the start, there's less room as well to fit in the things that might be more useful, might be more impactful. So where you start matters. What you say matters, where you start matters. And the big rocks at the company are not the company story. They're not the product. They're not the demo. They're not the founders.

[00:05:57] They're not even what the existing sellers are doing right now. These are not the big rocks. The big rocks are something else. And it's about how you actually sell the product that you're asking those new hires to go sell. So as I say, I've built a number of these programs. So let's talk about if I was in your shoes and you had to build something like this right now, what would I do? And let's say the goal is that we have our new hires up and running in four weeks. How would I structure this program?

[00:06:25] So first of all, and I think I've got one, two, three, four, I've got six points to make here. So not a whole load. So keep this in mind as we're going through this. The first thing I think, I think personally the most important thing is be very clear in your mind about what your objectives are for this new hire and what their objectives should be as they join the company. And then build the onboarding for those, whatever those objectives are.

[00:06:54] Now, most sales leaders, when they're DIYing a program, they feel this because they don't think about it quite the same way. They say, well, I want them ramped up, right? I want them to know this. I want them to know that. And frankly, you could have a list of 100 things that we want this person to know. And we've got no way of trying to figure out, well, what's the real way to prioritize those things if we're not very clear in the objectives. And when I build programs, there's two objectives that we start with.

[00:07:23] One is I want a new hire, an AE, to be after the first week. At the end of the first week, they should be able to prospect. They should be able to contact their friendlies. And maybe they're not so friendlies in their territory if they don't have a great network in there. And they should be able to start having a conversation, sending an email to say, I'm at a new company. Let's meet. Now, obviously, there's more depth than that.

[00:07:49] But there's certainly certain things they need to know to be able to have that conversation, very brief one, and to be able to send that email. And there are things such as this. The first one is what problems do we solve? And then the second one is for an ICP, right? So here's who usually buys our stuff. And here's the problems that we solve for them. That's a great place to start. Problems that we solve, not what our product does. Very closely aligned to that will be value props, right?

[00:08:17] So what does it mean when we solve those? We should arm them with a couple of short stories. These are not full customer stories, not necessarily case studies, but it's the four examples that might last 20 seconds, 30 seconds, right? So for people like you, friendly person, we solve these types of problems in this type of way, the value prop. And here's an example of someone that we've done it for recently, right?

[00:08:44] And the final thing they probably need to know to be able to prospect is what the differentiator is against the common situation that their prospect's going to be in. So it's the why change conversation. So if they do contact someone they already know, they're probably, if they know them well, they'll probably take the meeting anyway. I get it, John. You've joined your company. Sounds like you're excited. Let's talk, right? But for some of it would be, look, we've already got something in place.

[00:09:11] Or how would you be different to this thing that we have already? It might be a tool, it might be a process, it might be a team, whatever it might be. And be able to position against that. Oh, that's common. That happens a lot. Here's why people, even though they had that in place, will at least investigate whether what we have is worthwhile, right? So some sort of statement for the new hire so they can go in and answer that question. So that's it, right?

[00:09:36] And into that first week, if you can get them understanding the problems that we solve for an ICP, the value prop that goes aligned to that, one or two super short stories, basically for examples, right? And then whatever the common situation they'll get into, a way to handle that in terms of, oh, we're different because. Yeah, that's very common that you have X vendor. It's very common that you do things manually this way.

[00:10:01] The reason why people like you will still look at us and often become customers is this, some quick, compelling statement they can make for the why change, right? And at the end of the first week, I want to do everything I can so that person is confident and competent in picking up the phone, sending the email. If they start on the Monday, I want them to do it on the Friday. And I want evidence they're doing it on the Friday, right? BCC mean the email. Tell me who you've contacted. Tell me what they've said.

[00:10:30] Show me the meetings that you've booked by the end of that first week. So that's one thing to get very clear on in terms of objectives. The second objective that I work on is the idea at the end of the second week of them being on board is that they will be able to do a first meeting certification. All right. Now, what does that mean?

[00:10:51] This is why I say to the new hires I work with, I say, look, if you book a first meeting in the second week that you're there and for whatever reason, your head of sales, your manager, whoever it might be, doesn't show up on the call and you're left on your own. Can you handle that call? All right. That's the way I think about it because usually you won't leave them on their own. You'll actually be on the call with them. But let's say for whatever reason, the internet goes out at your home and you can join the call as well as your new hire.

[00:11:20] Can they handle that call? And so then let's think about what is needed to be able to handle that first meeting. First of all, we need to understand how to do the discovery. What are the really good questions to ask? Not the crappy ones, but what are the really compelling questions to ask? The great discovery. How do you position what we do? Is there a deck? Is there no deck? If there's no deck, what's the way to handle that? When it comes to the point in that first meeting where it says, well, what do you guys do? You've asked me enough questions. How do they handle that?

[00:11:50] Can we do deeper stories or more stories than we did in the prospecting? So what's the two-minute version of a story or the minute version of a story, not the 22nd version of the story? What objections will they usually come up against when they say, what about this? What about that? How do you handle this? I have someone that does that already. Things like that, right? How do they handle those objections? And then what are the usual next steps they should ask for at the end of that first meeting?

[00:12:17] So if you can get someone in the second week to be able to do all those things, imagine how fast, how further forward they will be than usual if they're doing that. Now, I'll tell you from experience is that the prospecting objective is usually pretty easy and sellers don't get too upset about that, right? They get it, right?

[00:12:42] The end of the second week to be able to handle a first meeting is a challenge, right? It makes them uncomfortable, right? It's not easy. This is a big ask that in two weeks into the job and the company, you can get really good at all this stuff. It's not easy to do, but I still do it. I really encourage it because, you know, it's a real forcing function. It makes them uncomfortable. It makes it force them to go learn now, not next week or tomorrow or the day after, right?

[00:13:09] And it helps us make sure that we have the right building blocks in place so that, you know, they're not just left to figure all these things out. We've got the things in place for them, right? So I really encourage you to think about that. At the end of that first, that second week, when I say certification, what I mean is they should be able to have that fake first meeting with the head of sales at the company.

[00:13:31] Whether it's you or, you know, if it's two, three layers of management at this point, they should be able to sit down on a Zoom for half an hour with the head of sales and then role play that. And the head of sales should sit there at the end of that half hour and go, yeah, this person is ready, right? I would feel comfortable this person going and doing this. Or they have to fail them if they're not. You can't give atta boys around this, right? Or atta girls. And say, look, you weren't good enough in these two areas.

[00:14:01] I was talking to them Monday, right? And there's a process to go through there. But it's all about making them uncomfortable but setting very clear objectives that this is what we expect you to be able to do at the end of the first week and in the second week. And by the way, here's all the support and the program that we have to help you get there. Now, during this process in just these first two weeks, daily checkpoints should be there. They should have the ability to come and ask questions. They should be able to role play things with you, run ideas past you, things like that.

[00:14:30] It has to be that feedback loop that you can't blow off and say, oh, really, sorry, I'm so busy. I can't do it today, right? This has to happen, daily checkpoints. And what they should get from the company are the frameworks and the assets to help them do this. And then you should give them drills to do, right? Whether it's send me your – by the end of Wednesday, the second week or Monday, the end of the first week, whatever it might be, send me your 20-second story. Send me your one-minute story.

[00:14:59] Give me a list of the types of questions you'll ask and why you're asking them. So ask them to come back at things to do some homework and feedback to you so it's not just a one-way thing. And then suddenly, at the end of the two weeks, they have to sit down and do this discovery call. So rethink through that process. Now, usually what I find is it's not a huge lift for the company to be ready for this. It's all about just getting some simple things in place that the new hire can go and listen to and take part in.

[00:15:30] Now, based on this, we've given them some first metrics to go ahead, right? They start prospecting and then secondly, can they do the first meeting? Think about, well, what's the actual metrics beyond that, right? And I really encourage companies to think about three things. And maybe there's things that are unique to your company that would be different. But one is self-generated pipe. How fast, for example, can they create their first self-generated opportunity? Okay.

[00:15:58] How fast can they book that first meeting? Things like that. Secondly, I would look at stage two qualified pipe or whatever stage it is in your sales force to say it's qualified pipe. So they found something and they booked some first meetings and there's some sort of pipeline there. But then secondly, what actually converts into qualified opportunities? Things like that is where you want to be clear with them that you expect after one month, they should be at this sort of profile, right?

[00:16:27] You would have booked this many meetings, held this many meetings and have this much qualified pipe, right? And you do it for the first month and the second month and the third month. And monitor that and coach them and help them and look for their early warning signs. They're not getting there, right? Because there's going to be some sort of problem that needs to be fixed if they're not hitting these metrics or getting close to them. All right. So that long thing was the first step to do.

[00:16:53] The second one to do is to think about personas, all right? So you think about what we did in the first one. We didn't do too much on ICP. Now, it's important to do this. So I would say this comes next, right? They need to be able to get deep, deep understanding of prospects and their problems.

[00:17:13] And here's a big aha is when we go back to that, the beaker at the front of the class is if you fill people's brains with what we just talked about in stage one and all about prospects and their problems, they're in a great position to then layer in, have the context for what, when they truly understand what our product does. Right?

[00:17:38] So the context that we're filling their brains with is the prospect and their problems, not the product. Right? And this is a big mistake that people make when they're doing this. Right? So we want them to understand deeply, here are the three main types of people that we deal with. Here's who they are. Here's what the day-to-day job's like. Here's the pressures they're under. Here's how they get measured. Here's the problems they might have. And I mean, all problems, not just the ones that we solve. Right?

[00:18:03] This is the challenges these people are going to relate to if you talk about challenges as opposed to features of our product. Right? And then we get focused around that and we go deep into this. And if you're going to have a conversation with this type of persona, here's some great questions to ask specific to that persona. So when we're doing this, they need to think about existing customers. And I bet you for many companies, you will have done some sort of recorded call with customers.

[00:18:32] Usually marketing does a bunch of these calls. There might be some CS calls you listen to, but really understand what's going on with existing customers. Go to YouTube videos on that type of persona. Right? I bet you if you did a quick search right now and said, I don't know, how do you get a job as a SOC leader? For example. There's going to be people in there talking about what SOC leaders do. Right? This is a great place to go find YouTube videos.

[00:18:58] Go sit down with your CS team and figure out, you know, what these customers, they're in my territory, let's say. What are these customers doing with us? What are they using to solve? What are they solving? What problems are they solving with our product? Things like that. Right? Go and look at those. And then also whatever conversation intelligence tool is gone or other ones out there. Go listen to those specific calls with those personas at that point to understand what it is that persona cares about.

[00:19:27] And maybe you give them a worksheet. Right? You say, look, for this persona, I want you to come back with these type, you know, five headings. Tell me all about what their job's like, the problems that they're trying to face, what problems do we actually solve for them? And then how might you ask questions that are relevant to that person? So that's step number two is get focused on personas. You're also going to find out or know already that these new hours coming in are going to have different levels of industry and market knowledge.

[00:19:57] All right? So some might be from a competitor and therefore know this and say that. Some might be even from outside of cyber and therefore not have a clue. So you need to think about, well, how do we get these people up to a level where they can converse with someone senior and a security leader? Right? Might not be the CISO, but CISO minus one or two, depending on the size of the company. Can they have a conversation about security or this segment of security with that person? Forget, you know, discovery and things like that.

[00:20:24] If they were just to sit there very casually over coffee, could they hold a conversation about this segment of the market? Now, to do that, they need to understand the history of the segment. Right? They need to know, well, when did it become a thing and why did it become a thing? Was it eight years ago, two years ago, 20 years ago? What's happened in that period of time that's evolved the segment? What pressures has the segment been under? What new issues or threats or trends have happened to the segment that caused us to be where we are today?

[00:20:54] What were the business drivers that caused those things to happen? Right? So really think through not the technical side to all this for a seller, but think through the business dynamics of this segment of cybersecurity. Why it exists? Why it still exists today? What's changed over the years? What pressures came in? Was there a big new market entrant that just took over the world? You think about firewalls, right?

[00:21:19] When Palo Alto came in, you basically had checkpoints and Cisco and maybe Fortinites before then. But the effect that Palo had was significant. And you hired in the firewall segment, you need to understand that history going back, even back to that. All right? Then, number four, this is when we get into our product, right? And I get it. There's going to be people listening to this or founders or whatever.

[00:21:45] There's no way that we should wait this long before they understand what our product does and seeing the magic of the product and seeing the demo and how we demo it and things like that, right? And I would caution you that if that's your thought process, I'm telling you, you've probably got it wrong. All right? Now, they need to understand the segment you're in and things like that. But what people do too often is flood them. The big rocks they put in their brain is here's our product. Go have the SE give you a demo. In fact, here's the founder going to give you a demo.

[00:22:15] And all these things about product, product, product. That's not what they need before now. At this point, we're now at the point. They've got the context of the ICP. They have the context of the problems that person faces. Now, when they watch the demo and hear about the product, they're putting it into the context of what they understand already about the persona. And that's the right way to do this, right? That's the right way around to do this.

[00:22:42] Be careful because they don't need to do everything about the product, right? At this stage, they need to understand the good things about it. Maybe they need to understand what the weak parts are about the product. They need to know why you demo it a certain way. Why don't you go over there? Does it not work, right? Or is it not quite as compelling? Or is it not a conversation we want to have? We don't want to open up a can of worms. So they need to understand these things. And I think one of the things they really need to understand very clearly with your product is what are the wow moments, right?

[00:23:12] These are the moments when someone sees the product who knows your competitors because they've used the competitors or whatever. What's the points in that process that they go, oh, wow. Oh, I get it, right? Sometimes wow moments, sometimes aha moments, right? The salesperson needs to understand definitely what those are and why they're aha moments, why they're wow moments.

[00:23:36] Because when they're doing their calls, they want to make sure they're driving prospects towards needing whatever that might be, right? So if your current demo, frankly, is like a half-hour demo and it's boring, boring, boring, and then suddenly it's an aha moment, you might have got this wrong, right? Because you want to bring the aha moments and the wow moments to the front. And a seller should know what they are so they tee them up appropriately, right? Now, beyond that, there are two things more they will need to know.

[00:24:04] One is that there's deep in all the things, some of the things we talked about, right? The really deep discovery questions, the really deep objection handling, the deep stories, deep history about the company, things like that, right? So this is where you start going a lot deeper than they've had already. They might have picked these things up along the way already, all right? So just because we don't have a formal bit in the process for these things, they probably learned from others or heard others go deeper. So they might have picked these up, but don't leave that to chance. So make sure that they go deeper.

[00:24:34] And then the final thing is what I call the everything else, all right? This is the things that we don't want to waste time on up to now. We don't want to waste time on Salesforce training about, well, how do we got medics set up inside Salesforce? They'll figure that out, right? Believe me, they'll figure that out. They don't need to have training on the marketing portal. All the things are there. They just, they'll figure that out, right?

[00:25:00] Whatever processes you have in place to book a demo or book a POV or set up a POV and things like that, they need to know that. Pricing is another one, right? They don't need to know pricing in the first two, three, four weeks of the company. If they do, that's awesome. It means they're starting to produce proposals, all right? You can solve that at a time. Pricing must come later. And then deep product knowledge is another thing to add in here.

[00:25:24] One of the things I completely disagree with others on, and I've heard this and seen this from sales leaders and, I don't know, industry leaders and people on sales LinkedIn, that great salespeople are product experts. I have not found any evidence over the years to show that this is true. Now, maybe in cybersecurity, it's a little bit different, right?

[00:25:48] And I'm very conscious that when you listen to and look at the posts on LinkedIn from the sales world, often what they're talking about are non-technical products, right? They're talking about sales productivity products, marketing products, things like that, right? And I get it, right? If you don't need a technical expert, then you'll probably have to do the demo yourself, which is fine because it's not a super technical product. You can probably get through with it.

[00:26:15] But certainly in cybersecurity, I have not seen any evidence to say that great salespeople are product experts. To me, that's a complete fallacy. In our world, the SE obviously is going to be the product expert. What we need to be as salespeople is one that understands how our product can solve problems. So we actually want to be experts in problems, not experts in products. So worth keeping that in mind.

[00:26:44] And what I'll say to you is that it's easy to come up with a long list of things to train them on. In fact, I was working with a company probably two years ago and the sales leader came off the list of 120 things that the salespeople probably need to be trained on. The trick is how do you narrow that down? And if you come from the lens of being clear on objectives, then you're going to be in a much better position to design your DIY program. So you're hitting those objectives as opposed to just thinking, okay, we've got a long list of things to get through.

[00:27:12] And often what happens when you get a long list of things to get through, you essentially end up giving it to the new eye or saying, well, go learn these things, right? Go figure this bit out. So these six points I gave you will help you get focused and deliver a really good onboarding program when you don't have someone to do it for you.

[00:27:38] It will mean a lot to me and to the continued growth of the show if you'd help get the word out. So how do you do that easily? There are two ways. Firstly, just simply send a link to a friend, send a link to the show, to this episode. You can email it, text it, Slack it, whatever works for you and is easy for you. The second way is to leave a super quick rating. And sometimes that can seem complicated. So I've made it as easy for you as I can.

[00:28:04] You simply have to go to ratethispodcast.com slash cyber. That's ratethispodcast.com slash cyber. And it explains exactly how to do it. Either of these ways will take you less than 30 seconds to do and it will mean the world to me. So thank you.