B2B sales hiring for startups [1 hour crash course]

by Crystal Williams

Ready to hire salespeople but don’t know where to start? You’re in the right place. Steli Efti, the CEO of Close.io, recently did a webinar on B2B sales hiring. Although it’s geared towards B2B companies and startups, the principles can be applied to most companies.

He has helped over 200 venture-backed startups scale their sales and is excited to share the lessons he’s learned with you. He covers everything you need to know about sales hiring such as when to hire salespeople, what traits to look for or avoid, how to train them and more. Watch the video or read the transcript below.

 We’re releasing our latest book, The Sales Hiring Playbook, soon. Be among the first to get a free copy.

Transcript

Steli Efti: Boom! Perfect. All right, let me—this is one of those things. Let me hit Play. Control Panel. Beautiful. All right, ladies and gentlemen. Hey, Matteo. Good to see you guys. So—yeah. Let’s rock and roll. Welcome everybody to today’s webinar. This is going to be a good one. I’m really excited about this one. So, I’m going to go through kind of the ABC’s and the basics of sales hiring specifically for B2B companies and startups, but really most of these base principles apply to most companies out there.

So, I’m going to keep the content fairly short and on point and really want to lean more heavily on the Q&A side of things. So I’m going to go through the basics of hiring amazing talent, onboarding that talent really successfully and then we’re going to have a conversation. And mainly, I want to just answer your questions, right? So, hopefully, you have a bunch of questions already coming into this. If you don’t, make sure to come up with questions as I’m going through these slides. And as you are thinking of questions, start writing them out in chat.

I’m not going to be stopping the—I’m not going to be responding to them in real time, but by the end of—when we get to the Q&A section, if I already have a bunch of questions in chat, it’s just going to make this webinar a lot more content-intensive because I’m going to be able to launch right into answering some of these questions.

Steli's background: Pivoting from ElasticSales to Close.io

All right. So, let’s get started. Sales Hiring 101, you know, how to hire and manage, you know, amazing sales talent for your B2B company. So that’s what we’re going to talk about today. I know most of you people already know me, know my background but just to run through the reason why both I care and know a thing or two about how to hire sales talent, how to grow sales teams or organize and structure sales teams and set salespeople up for success.

We used to run a company called ElasticSales where we were running a large sales organization and we’re helping over 200 venture-backed startups in Silicon Valley, scaled their sales efforts internally and externally. And as part of running ElasticSales as many of you know, we built a little piece of internal software called Close.io.

It’s our kind of magical CRM that’s focused on empowering sales teams, close more deals, make more revenue, make things happen. And with Close.io today, there is thousands and thousands of sales teams all around the world that are using our platform and are growing their teams based on Close.io and I personally am talking to—I don’t know how many founders—but it’s more than—it’s probably like 5 to 10 founders and sales leaders every single week giving them advice on how to retain, how to acquire, how to manage, how to coach sales talents. So, we live and breathe this stuff every single day. We see an incredible amount of best practices, experimentation, things that companies do that work, things that companies attempt that don’t work and it’s just a lot of accumulation of knowledge that I want to make, you know—I want to make accessible to you and that’s the whole purpose of this is taking all the lessons and learnings and know-how that we have accumulated and sharing it with you guys so you can be more successful. Simple as that. So, with that being said, let’s launch right into some of the basics of sales hiring and sales management and then, you know, for me even more excitingly, we’ll get to your questions and my answers to those. All right.

So, we live and breathe this stuff every single day. We see an incredible amount of best practices, experimentation, things that companies do that work, things that companies attempt that don’t work and it’s just a lot of accumulation of knowledge that I want to make, you know—I want to make accessible to you and that’s the whole purpose of this is taking all the lessons and learnings and know-how that we have accumulated and sharing it with you guys so you can be more successful. Simple as that. So, with that being said, let’s launch right into some of the basics of sales hiring and sales management and then, you know, for me even more excitingly, we’ll get to your questions and my answers to those. All right.

So, with that being said, let’s launch right into some of the basics of sales hiring and sales management and then, you know, for me even more excitingly, we’ll get to your questions and my answers to those. All right.

Startup sales hiring framework

Step #1: Founder-driven sales

So, first of all, let me share my framework of startup sales hiring in general. Again, this applies to any kind of business really. I think Step #1, you know, the most fundamental thing you have to do is that you have to sell yourself first, and it doesn’t matter if—like at the beginning obviously that’s the founders but even if somebody in here is the first salesperson that works at that B2B startup or company and you’re like “I’m not a founder, but I’m the first sales guy or gal.” The same step applies to you. First, you have to sell, right? No matter if you have a sales background or not, no matter if selling is going to be ultimately the thing you’re going to do forever or just for certain period of time. There’s no way around this. At the beginning, the founders need to sell or the first sales person needs to, you know, do the job themselves. Whatever job you’re trying to hire people for, you have to be able to perform that job yourself even if you do it poorly. In order to understand what the job entails and how to hire effectively for that job and how to set other people up for success in that job, you have to do it. So, Step #1, there’s no way around this, and I know a lot of people want to avoid this and find work around to this, but Step #1 no matter who you are and what your situation is and no matter how much you think you’re not a salesperson, you have to sell yourself first. Once you’ve done it and I always say this is—Step #1 is being a shitty salesperson yourself, right?

First, you have to sell, right? No matter if you have a sales background or not, no matter if selling is going to be ultimately the thing you’re going to do forever or just for certain period of time. There’s no way around this. At the beginning, the founders need to sell or the first sales person needs to, you know, do the job themselves. Whatever job you’re trying to hire people for, you have to be able to perform that job yourself even if you do it poorly. In order to understand what the job entails and how to hire effectively for that job and how to set other people up for success in that job, you have to do it. So, Step #1, there’s no way around this, and I know a lot of people want to avoid this and find work around to this, but Step #1 no matter who you are and what your situation is and no matter how much you think you’re not a salesperson, you have to sell yourself first. Once you’ve done it and I always say this is—Step #1 is being a shitty salesperson yourself, right?

In order to understand what the job entails and how to hire effectively for that job and how to set other people up for success in that job, you have to do it. So, Step #1, there’s no way around this, and I know a lot of people want to avoid this and find work around to this, but Step #1 no matter who you are and what your situation is and no matter how much you think you’re not a salesperson, you have to sell yourself first. Once you’ve done it and I always say this is—Step #1 is being a shitty salesperson yourself, right?

Step #2: Founder sales manager

So, once you’ve done the job yourself even if you’ve done it poorly, you get to Step #2. And Step #2 is that now you move from being maybe a poor or mediocre salesperson yourself or some of you might be amazing salespeople; it doesn’t really matter. You move from doing sales yourself to now managing salespeople. In most startups, you want the founders to be the first ones that are going to be attempting to do a little bit of sales management themselves. And with founders, I joke oftentimes that you go from being a bad salesperson to being a bad sales manager. That’s totally cool. It’s totally fine. The healthy way of approaching this is when you do sales yourself, you’re trying to attempt and prove that there’s a market out there. You can get customers. You can acquire customers. Once you’ve got a bunch of customers, now what you’re trying to do in Step #2 is you try to bring in some junior talent and I’m going to talk about this in detail now, but you’re going to bring in some junior talent to prove “Can I teach anyone else to generate some results?” Or “Can I teach other people to generate the same results I’ve generated?” That’s really the question you’re trying to answer in Step #2 and this is for most people where, you know, hiring starts is you go out there and you hire the first few people to figure out “Is it possible for me to replicate the success that we’ve had

Once you’ve got a bunch of customers, now what you’re trying to do in Step #2 is you try to bring in some junior talent and I’m going to talk about this in detail now, but you’re going to bring in some junior talent to prove “Can I teach anyone else to generate some results?” Or “Can I teach other people to generate the same results I’ve generated?” That’s really the question you’re trying to answer in Step #2 and this is for most people where, you know, hiring starts is you go out there and you hire the first few people to figure out “Is it possible for me to replicate the success that we’ve had selling with other people?” That’s really the basis of that. And

And in that stage, in that Step #2, you really want to hire more junior sales talent. That is not the time to go and hire people that have 50 years of experience. That’s not the time to hire people that are VPs of sales of other companies to do selling for you. At that stage, you really just want to have some junior talent that’s going to come in that has some basic hustle gene, people that are young, ambitious, hungry, sharp, smart and passionate and that you can teach the ABC’s of what you’ve been doing for them to replicate. Now, these people, these junior salespeople that you’re trying to hire, these people are not going to be—so what you’re looking for there is not many years of experience but what you’re still looking for is core DNA. You’re looking for somebody that does have some level of killer instinct, that has some level of competitiveness, that is a good communicator, that likes people and could be liked by other people, somebody that has mental strength and discipline. Like these certain traits that you can’t teach somebody and a killer instinct to try to go for a close or to pick up the phone and call somebody with a high level of possibility of being rejected. These types of things you don’t want to have to teach somebody. You want people that already have that kind of in their gene, in their personality. What you want to teach them is you want to them about your product, about your market and then you want to teach them the ABC’s of here’s how you write an email, here’s how you prospect. You want to teach them the basics of performing the job, but you don’t want to teach them what it takes to be somebody that could be good in sales, and we’ll talk about this a little bit more in detail later. So, somebody asked and I can answer this on this slide immediately. “What makes somebody a junior talent? What defines junior talent?” Junior talent defined—junior means somebody that does not have many years of experience, maybe one year of business experience but surely not 10, 20, 15 years of experience in a traditional sales job, but that has

You’re looking for somebody that does have some level of killer instinct, that has some level of competitiveness, that is a good communicator, that likes people and could be liked by other people, somebody that has mental strength and discipline. Like these certain traits that you can’t teach somebody and a killer instinct to try to go for a close or to pick up the phone and call somebody with a high level of possibility of being rejected. These types of things you don’t want to have to teach somebody. You want people that already have that kind of in their gene, in their personality. What you want to teach them is you want to them about your product, about your market and then you want to teach them the ABC’s of here’s how you write an email, here’s how you prospect. You want to teach them the basics of performing the job, but you don’t want to teach them what it takes to be somebody that could be good in sales, and we’ll talk about this a little bit more in detail later. So, somebody asked and I can answer this on this slide immediately. “What makes somebody a junior talent? What defines junior talent?” Junior talent defined—junior means somebody that does not have many years of experience, maybe one year of business experience but surely not 10, 20, 15 years of experience in a traditional sales job, but that has

You want people that already have that kind of in their gene, in their personality. What you want to teach them is you want to them about your product, about your market and then you want to teach them the ABC’s of here’s how you write an email, here’s how you prospect. You want to teach them the basics of performing the job, but you don’t want to teach them what it takes to be somebody that could be good in sales, and we’ll talk about this a little bit more in detail later. So, somebody asked and I can answer this on this slide immediately. “What makes somebody a junior talent? What defines junior talent?” Junior talent defined—junior means somebody that does not have many years of experience, maybe one year of business experience but surely not 10, 20, 15 years of experience in a traditional sales job, but that has

So, somebody asked and I can answer this on this slide immediately. “What makes somebody a junior talent? What defines junior talent?” Junior talent defined—junior means somebody that does not have many years of experience, maybe one year of business experience but surely not 10, 20, 15 years of experience in a traditional sales job, but that has talent to do sales. And the talent to do sales in most cases will mean this is somebody I would want to buy from. This is somebody that is fearless. This is somebody that hustles. This is somebody that wants to communicate. This is somebody that has a high level of tolerance for rejection. You’re looking for these types of things. And—We’ll talk about

And—We’ll talk about kind of, you know, about the personality type of salespeople that most startups should try to hire for a little later. So I’m going to drop to that question in a bit, but we go from Step 1—we’re doing all the selling ourselves—to Step 2, we are hiring some junior people to teach what we’ve been doing and see can we get some results, and at this stage, things are still very much in motion. They’re fluid. You’re not looking for perfection. You’re still experimenting. You’re experimenting. You’re trying to figure out some kind of a process that creates some kind of—some results that you can, you know, base on. And also, in that step and stage #2, one base tip in general when it comes to sales hiring and I’ll throw out there early is you want to hire in triples, if not, in couples, even better in triples, which means if you want to hire one salesperson, you really want to bring in three people to see who’s going to be that one person that’s going to stand out and be the perfect type of person to do the job because if you just hire one junior salesperson and you are let’s say a more inexperienced sales manager

And also, in that step and stage #2, one base tip in general when it comes to sales hiring and I’ll throw out there early is you want to hire in triples, if not, in couples, even better in triples, which means if you want to hire one salesperson, you really want to bring in three people to see who’s going to be that one person that’s going to stand out and be the perfect type of person to do the job because if you just hire one junior salesperson and you are let’s say a more inexperienced sales manager yourself. Now, if that person doesn’t perform well, you don’t really know what the problem is. You don’t know if it’s the salesperson or if it is your product or if it is the way you manage. You don’t know where the blame lies. Now if you hire two or three people, ideally three people that are very different in their characteristic and their background and their personality. You hire people that look and act a little differently and you give them the same training, the same product, the same leads and you see is there a difference in terms of how they perform. If they all perform equally poor, maybe the problem is

Now if you hire two or three people, ideally three people that are very different in their characteristic and their background and their personality. You hire people that look and act a little differently and you give them the same training, the same product, the same leads and you see is there a difference in terms of how they perform. If they all perform equally poor, maybe the problem is on you or your product. But if one of them—typically one of them will outperform the other two and that gives you a lot of information and a strong signal on what type of person will do really well in your company. So, I always advise to hire in threes when it comes to salespeople. Competition is healthy in sales. Measuring yourself with other people is really healthy. It’s going to always be hard to measure somebody that’s just started with your results, you know. You might have been with the company for a little while. Now you bring in somebody new. That person obviously is not selling as well as you. Now, how do you compare their performance? How do you benchmark their performance? It’s always tricky. But if you bring in three new people and they all start on day 1, it’s very easy to benchmark. You can look at all the results that all three generate with the same training, the same amount on the job and you can clearly see the differences in their abilities and what they’re capable of doing or not.

Competition is healthy in sales. Measuring yourself with other people is really healthy. It’s going to always be hard to measure somebody that’s just started with your results, you know. You might have been with the company for a little while. Now you bring in somebody new. That person obviously is not selling as well as you. Now, how do you compare their performance? How do you benchmark their performance? It’s always tricky. But if you bring in three new people and they all start on day 1, it’s very easy to benchmark. You can look at all the results that all three generate with the same training, the same amount on the job and you can clearly see the differences in their abilities and what they’re capable of doing or not.

Step #3: Junior sales leader

So, you do it yourself in Step 1 and Step 2, you bring in some junior people, two to three of them at once, and you see can I replicate some of the results that we’ve been doing. And once you’ve done that and you get some kind of results. You’re closing deals. You’re making revenue. You may or may not be killing it yet. Even if it’s very slow. Even if it’s not as profitable or quite as amazing as you think it should be, if you have some kind of result and you have some kind of repeatability with those results, then you’re getting to territory of Stage #3 which is when you want to bring in a junior sales leader. This is somebody—here’s how I define this person. This is somebody that has been a sales manager for a relatively short period of time but relatively successfully. Ideally, this is somebody that has been where you are right now in your stage a year or two ago. So, you want to hire somebody that works at a company that two years ago they were where you are right now and they have grown past that stage. The reason why you want to do that is you want to benefit and bank on all the lessons that this person learned at company X to come in and instantly gain a massive ROI from that. So, you want to bring in somebody that was a junior sales manager which means a sales manager with one or two years of experience—successful experience at a startup that’s just a step or two ahead of you. You bring in that person. You recruit and hire that person. That person now comes in and there’s already a team, right? You’ve been managing a small team. There’s already some results. There’s revenue. There’s some stuff going on and that person will immediately be able to identify what you’re doing wrong, what are easy wins that they’ve experienced and proven at the other company that they can immediately bring

This is somebody—here’s how I define this person. This is somebody that has been a sales manager for a relatively short period of time but relatively successfully. Ideally, this is somebody that has been where you are right now in your stage a year or two ago. So, you want to hire somebody that works at a company that two years ago they were where you are right now and they have grown past that stage. The reason why you want to do that is you want to benefit and bank on all the lessons that this person learned at company X to come in and instantly gain a massive ROI from that. So, you want to bring in somebody that was a junior sales manager which means a sales manager with one or two years of experience—successful experience at a startup that’s just a step or two ahead of you. You bring in that person. You recruit and hire that person. That person now comes in and there’s already a team, right? You’ve been managing a small team. There’s already some results. There’s revenue. There’s some stuff going on and that person will immediately be able to identify what you’re doing wrong, what are easy wins that they’ve experienced and proven at the other company that they can immediately bring

So, you want to bring in somebody that was a junior sales manager which means a sales manager with one or two years of experience—successful experience at a startup that’s just a step or two ahead of you. You bring in that person. You recruit and hire that person. That person now comes in and there’s already a team, right? You’ve been managing a small team. There’s already some results. There’s revenue. There’s some stuff going on and that person will immediately be able to identify what you’re doing wrong, what are easy wins that they’ve experienced and proven at the other company that they can immediately bring in to—they’ll immediately bring in some more sales talent. They’ll organize and structure things a little bit better. They cut some stupid things you’re doing. They add some smart things that they’ve learned. They’re instantly going to get you to that next level, and that’s going to make a massive difference. And I’m going to be rocking—like keep the questions going. I love the quality and

And I’m going to be rocking—like keep the questions going. I love the quality and the quantity of questions. Just keep them going. I’m going to be ignoring them for now because I just have a few slides to get through and then I’m going to come back and really do an intensive Q&;A section. So just keep them coming as you can think of them. So, Step 1, you do it yourself. Step 2, you manage a few people—junior people to see if they can do it. Step 3, you bring in some junior sales leadership that has a bit more experience than you in managing people, a year or two ahead of you. They come in. They bring instant wins. They grow the team. They grow your efforts. They mature your efforts and maybe they start growing one or two junior sales leaders under them and then once that—once you get to the point where your sales model is both predictable and repeatable and you think “We got it. We know exactly what amount of sales we’re going to do next month. We know exactly how to double the sales that we’re doing. We know the mechanics. We know the formula. Now, we need to scale this as fast as possible.”

So, Step 1, you do it yourself. Step 2, you manage a few people—junior people to see if they can do it. Step 3, you bring in some junior sales leadership that has a bit more experience than you in managing people, a year or two ahead of you. They come in. They bring instant wins. They grow the team. They grow your efforts. They mature your efforts and maybe they start growing one or two junior sales leaders under them and then once that—once you get to the point where your sales model is both predictable and repeatable and you think “We got it. We know exactly what amount of sales we’re going to do next month. We know exactly how to double the sales that we’re doing. We know the mechanics. We know the formula. Now, we need to scale this as fast as possible.”

Step #4: Senior sales leader

That’s when you get to Stage #4 which is when you bring in some serious senior sales leadership. So what that means is that now you bring in the VP of sales. Now you bring in the guy or gal that’s been doing this job for 10 years, that’s been a VP of sales at one or two other companies successfully and that person comes in and that person needs this structure to shine. That person comes in and there’s already one or two sales managers. There’s a team of 10, 20 people, 30 people, whatever it is and now that person will do things to help scale this effort. This person will set up a compensation structure that’s really scalable. This VP of sales is going to set up a recruiting and hiring structure that’s really scalable. This VP of sales is going to create a training and career program, is going to redesign the organization structure of the sales team. This VP of sales is going to do all these things that are required to really scale your organization. Now, too many startups or sales, you know, people that need sales in their company, they make the mistakes that they want to hire this VP of sales right away. A VP of sales in Stage #2 is horrible. That person has not been selling themselves for many, many years. They have talents, the experience, the know-how, the skillset. Has not been trying to figure out how to sell something that nobody has ever heard of and that is very unproven and that maybe in three months, you’re going to have to pivot anyways and do something completely different. That is not the stage to hire super-senior salespeople. That’s why you want to do it at the right time, at the right stage. You do the right thing at the wrong time, you’re fucked, right? You’re trying to, you know, get in your garden when it’s snowing and it’s winter and try to like make things grow there. It’s not going to be a good time. So, you want to make sure that you bring in the right people at the right time when they really can give your business a boost. First, you do it yourself, then you help others do it, then you bring in somebody that has proven that they can teach and coach others doing it much better than you, somebody with a bit of experience. And once that’s rocking and rolling and you have a model that’s ready to scale, you bring in kind of the executive, kind of CEO of your sales team, the VP of sales, the director of sales, the person that’s a real kind of sales leader at the very high level and that person kind of orchestrates the organization to grow in and scale up really, really fast. All right. That being said, as a bunch of basic questions that people have when it comes to hiring, again, I’m going to go through with them really quickly and then we’re going to really focus and hone in on the Q&A section. So, first, a basic question is, you know—well, it’s actually not true.

This VP of sales is going to set up a recruiting and hiring structure that’s really scalable. This VP of sales is going to create a training and career program, is going to redesign the organization structure of the sales team. This VP of sales is going to do all these things that are required to really scale your organization. Now, too many startups or sales, you know, people that need sales in their company, they make the mistakes that they want to hire this VP of sales right away. A VP of sales in Stage #2 is horrible. That person has not been selling themselves for many, many years. They have talents, the experience, the know-how, the skillset. Has not been trying to figure out how to sell something that nobody has ever heard of and that is very unproven and that maybe in three months, you’re going to have to pivot anyways and do something completely different. That is not the stage to hire super-senior salespeople. That’s why you want to do it at the right time, at the right stage. You do the right thing at the wrong time, you’re fucked, right? You’re trying to, you know, get in your garden when it’s snowing and it’s winter and try to like make things grow there. It’s not going to be a good time. So, you want to make sure that you bring in the right people at the right time when they really can give your business a boost. First, you do it yourself, then you help others do it, then you bring in somebody that has proven that they can teach and coach others doing it much better than you, somebody with a bit of experience. And once that’s rocking and rolling and you have a model that’s ready to scale, you bring in kind of the executive, kind of CEO of your sales team, the VP of sales, the director of sales, the person that’s a real kind of sales leader at the very high level and that person kind of orchestrates the organization to grow in and scale up really, really fast. All right. That being said, as a bunch of basic questions that people have when it comes to hiring, again, I’m going to go through with them really quickly and then we’re going to really focus and hone in on the Q&A section. So, first, a basic question is, you know—well, it’s actually not true.

So, you want to make sure that you bring in the right people at the right time when they really can give your business a boost. First, you do it yourself, then you help others do it, then you bring in somebody that has proven that they can teach and coach others doing it much better than you, somebody with a bit of experience. And once that’s rocking and rolling and you have a model that’s ready to scale, you bring in kind of the executive, kind of CEO of your sales team, the VP of sales, the director of sales, the person that’s a real kind of sales leader at the very high level and that person kind of orchestrates the organization to grow in and scale up really, really fast. All right. That being said, as a bunch of basic questions that people have when it comes to hiring, again, I’m going to go through with them really quickly and then we’re going to really focus and hone in on the Q&A section. So, first, a basic question is, you know—well, it’s actually not true.

All right. That being said, as a bunch of basic questions that people have when it comes to hiring, again, I’m going to go through with them really quickly and then we’re going to really focus and hone in on the Q&A section. So, first, a basic question is, you know—well, it’s actually not true.

Where do you find sales talent?

Well, let’s start this way. First question is “Where the hell do I find sales talent?” Right? That’s really the first question that most people have. Where can I find the greatest salespeople ever? Well, I’ll tell you where you won’t find them. You won’t find most great sales talent by posting on some generic job board and saying “We’re hiring salespeople.” Most companies especially startups will not have a great time with this. Here’s the reality. Here’s the truth of selling, a few truths. Number one, nobody grows up wanting to be a salesperson, which means that by definition most of the magical sales—most of the people that are crushing it in sales, most of the best sales talent, for most of their life, they did not think of themselves as salespeople or as people that want to be in sales. So, what that uncovers is that there’s an incredible amount of sales talent out there that does not consider themselves salespeople and would not consider themselves as looking for a sales job. That’s really important to consider, and I’ll tell you some stories that from ElasticSales day. But before I get to that, that’s one thing you need to keep in mind.

Number one, nobody grows up wanting to be a salesperson, which means that by definition most of the magical sales—most of the people that are crushing it in sales, most of the best sales talent, for most of their life, they did not think of themselves as salespeople or as people that want to be in sales. So, what that uncovers is that there’s an incredible amount of sales talent out there that does not consider themselves salespeople and would not consider themselves as looking for a sales job. That’s really important to consider, and I’ll tell you some stories that from ElasticSales day. But before I get to that, that’s one thing you need to keep in mind.

Avoid senior sales hires early on

The other thing you need to keep in mind about sales talent is that if somebody—so there’s two categories, right? If somebody has a lot of experience, a lot being 5 to 10 years of sales experience and they are good, you cannot hire them, right? Maybe you can if they’re your brother, your mother, your sister, your grandfather, your uncle, your best friend since childhood, you know, competitive advantage is unfair. But most people that are—somebody who’s really good at sales and they have been doing sales for a while, they’re not looking for a job. They’re not applying for your job post on Craigslist. They’re not in the market looking for work. They’re making a ton of fucking money and they are in high demand. They are being recruited. They’re not looking for jobs. So most people that have many, many years of experience, if they are good, they’re out of the question for you. If you find somebody that applies for your job and has many years of experience and tells you they are amazing, you should be scared. There’s something wrong here. There’s something wrong here, right? There’s something that fundamentally does not compute.

They’re not applying for your job post on Craigslist. They’re not in the market looking for work. They’re making a ton of fucking money and they are in high demand. They are being recruited. They’re not looking for jobs. So most people that have many, many years of experience, if they are good, they’re out of the question for you. If you find somebody that applies for your job and has many years of experience and tells you they are amazing, you should be scared. There’s something wrong here. There’s something wrong here, right? There’s something that fundamentally does not compute.

How to recruit people who have sales potential

So, if we take off most people that have many, many years of sales experience as people that we can hire from, we have to look for people that have less experience, and I’ll tell you in the more junior bracket of sales hiring talent, we at ElasticSales, we were building one of the best sales teams in technology history. We were doing sales for hundreds of other B2B companies. All of our sales hires, all of them were people that had never had a sales job before and that did not apply for a sales job and they were not thinking of themselves as salespeople. We were aggressively recruiting people that did not want to have a sales job and here’s how we did it. You know, the first person that I hired as a salesperson was a founder of a failing startup, a guy that was actually an engineer, that actually worked at NASA and worked on the Mars Rover landing like a rocket. Like I always joke sales is rocket science but just in case we got us

All of our sales hires, all of them were people that had never had a sales job before and that did not apply for a sales job and they were not thinking of themselves as salespeople. We were aggressively recruiting people that did not want to have a sales job and here’s how we did it. You know, the first person that I hired as a salesperson was a founder of a failing startup, a guy that was actually an engineer, that actually worked at NASA and worked on the Mars Rover landing like a rocket. Like I always joke sales is rocket science but just in case we got us one, like this was a guy with zero sales experience but he had sales talents. He was a good communicator. He was a people person. He was somebody with a massive tolerance for pain and rejection and was somebody that was hustling his ass off as a founder of his own startup. He had all the building blocks of a great salesperson. So that was the first person I recruited and convinced that learning to sell would make him a better entrepreneur long-term, that making a good amount of money right now was important because his startup was failing and that being part early on of what we were building would be something really special. I recruited him based on that premise more than anything else. And then, I did what I always do. I asked every single hire that’s great, “Hey,” on their first day, “who is somebody that—who is the first person that comes to mind that you think would be amazing

He was a good communicator. He was a people person. He was somebody with a massive tolerance for pain and rejection and was somebody that was hustling his ass off as a founder of his own startup. He had all the building blocks of a great salesperson. So that was the first person I recruited and convinced that learning to sell would make him a better entrepreneur long-term, that making a good amount of money right now was important because his startup was failing and that being part early on of what we were building would be something really special. I recruited him based on that premise more than anything else. And then, I did what I always do. I asked every single hire that’s great, “Hey,” on their first day, “who is somebody that—who is the first person that comes to mind that you think would be amazing

And then, I did what I always do. I asked every single hire that’s great, “Hey,” on their first day, “who is somebody that—who is the first person that comes to mind that you think would be amazing at sales but would not never ever in a million years work here? Who’s somebody you know that would never fucking work here? But if we could make that happen, it would have been like game-changing for our company.” I’m asking people to give me recommendations for people that are unhireable, that I cannot hire. I ask them, “Who’s somebody I can’t hire that you love and you think is incredibly talented?” And what do I do once I get that name? I call them right there and then. And here’s my pitch to that person, I go “Hey, I’m just—you know, it’s the first day of Bob. So Bob is a good friend of

And here’s my pitch to that person, I go “Hey, I’m just—you know, it’s the first day of Bob. So Bob is a good friend of yours he told me. We just hired him. It’s his first day. The reason why I’m calling is anytime I hire somebody new, I ask them who’s the smartest person you know, somebody we would never be able to hire, and Bob said you. He said you are incredible. You are this. You are that. You’re the other. You’re the most amazing person ever. And you know what, I love to meet amazing people. So independently from us being able to hire you or not, I just wanted to get to know you a little bit.” Nobody rejects that. Everybody loves to be amazing. Everybody loves to be, you know, called by the founder or CEO or the director of sales and be saying, “Hey, this new hire—your friend said you’re the most amazing person they know.” What do I do then? I get to know them and I try to figure them out and I try to figure out what they’re trying to do in life, where they are right now and what they’re going to do next and I tell them about us and our vision and what we’re trying to do and why it’s special. And I basically sell them on the vision and the company and myself and the team, more so than on the job. And at the

What do I do then? I get to know them and I try to figure them out and I try to figure out what they’re trying to do in life, where they are right now and what they’re going to do next and I tell them about us and our vision and what we’re trying to do and why it’s special. And I basically sell them on the vision and the company and myself and the team, more so than on the job. And at the end if the conversation goes well, I tell them, “You know what, this was such a good conversation. I’d love to have you just come in for a day or two just brainstorm with the team, get to know us, give us feedback. I think you’re really smart. I think you’re really talented.” And step-by- step, they come in and it’s a dating process where they and us fall in love with each other and then at the end of it, they go “Holy shit! I guess now I’m in sales.” Like we hire as I said an electrical engineer that was a founder as a salesperson. We hired somebody that had just been accepted by Harvard Business School. His lifelong dream was to get an MBA at Harvard. He was working at a PR agency in New York. He never wanted to be in sales. He was preparing to go to Harvard. He spent a weekend with us. Next thing you know he relocated and started as a salesperson for us. I could go on

We hired somebody that had just been accepted by Harvard Business School. His lifelong dream was to get an MBA at Harvard. He was working at a PR agency in New York. He never wanted to be in sales. He was preparing to go to Harvard. He spent a weekend with us. Next thing you know he relocated and started as a salesperson for us. I could go on

I could go on story for story for story. All the people we hired were all coming in through internal recommendations and they were—none of them had any sales background, but all of them had sales talent and then we trained them and we made them great. And all of them today, by the way, all the entire first 20 hires at ElasticSales that were like our first sales hires, all of them today are directors of sales, VPs of sales or CEOs and founders of their own successful startups. Where do you find talent? Anywhere and everywhere. You just have to look differently. Don’t go and try to find people that are salespeople. Try to find people that have sales talent. How do I get—? There you go.

How to interview salespeople

Now, how do you interview salespeople? Very briefly on that. It’s actually very simple. So, philosophically I want you guys to understand this one simple truth: You don’t know if somebody is great at sales until they’ve proven it consistently. There’s no way that you can interview somebody to know for certain if they’re going to be great at the job of selling for more than a day or two, right? Some people are just amazing at interviewing, but that will not always translate into the actual job of selling. So—is there some things that you can do

There’s no way that you can interview somebody to know for certain if they’re going to be great at the job of selling for more than a day or two, right? Some people are just amazing at interviewing, but that will not always translate into the actual job of selling. So—is there some things that you can do on the interviewing process? Of course. Give them some homework, like have them sell you. That’s first, right? Don’t just ask them how were your revenue structures? Would you like to sell? No. Have them pitch you something.

That’s first, right? Don’t just ask them how were your revenue structures? Would you like to sell? No. Have them pitch you something.

If they’ve had a sales job before, have them sell you that product. If they have never ever sold anything, have them sell something that they use and like, “Hey, do you like your iPhone? What’s your favorite software product?” “Oh, I fucking love Gmail” or “I fucking love Facebook or Twitter,” or “I’m a huge Snapchat fan.” “Cool. Pitch me Snapchat, right? Sell me on it.” Let them pitch you. Let them prove to you that they’re capable of doing it. It’s like saying, “What kind of interview questions can I ask somebody to know if they’re going to be an NBA basketball superstar?” I mean, of course, I can ask some questions to know if they’re going to be

Let them pitch you. Let them prove to you that they’re capable of doing it. It’s like saying, “What kind of interview questions can I ask somebody to know if they’re going to be an NBA basketball superstar?” I mean, of course, I can ask some questions to know if they’re going to be culture-fit, if they’re smart, if they’re asked a question, they’re good communicators. But at the end of the day, I have to throw that person a ball and have them play. There’s no question I can ask on a piece of paper that somebody could answer that would make me know and spot if someone is going to be an NBA basketball superstar. I need to see them play the ball. So, throw them the ball as quickly as possible.

Have them pitch you something. Have them—I always like to do this exercise. Have them write a cold email. Here’s what I tell people. At Close.io, we don’t even do any cold emailing right now, but I would still give this exercise to people. “Hey, here’s how our core customer is, ideal customer. Here’s what our product does. Here’s an exercise for you. I want you to go out there on the web and research a company that you think would be an ideal customer for us. Then, I want you to find a person at that company that you think would be the ideal buyer, and then I want you to write an email to that person that would convince them to get into

Have them write a cold email. Here’s what I tell people. At Close.io, we don’t even do any cold emailing right now, but I would still give this exercise to people. “Hey, here’s how our core customer is, ideal customer. Here’s what our product does. Here’s an exercise for you. I want you to go out there on the web and research a company that you think would be an ideal customer for us. Then, I want you to find a person at that company that you think would be the ideal buyer, and then I want you to write an email to that person that would convince them to get into conversation with us. And I want you to send that email to me as if I was that person. And then I want you at the end of that email to describe to me your philosophy, your strategy of how did you come up with that company, how did you come up with that person within that company, why did you write the email the way you wrote it, what was your strategy, what was your thought process behind it.” I give them that task.

That tells you a shit ton about them, not just what kind of company they’d find, what kind of person, what subject line they’ll write, what the email is and what their thought process was behind it, but also how much time it took them to do that. Like all that is a ton of lessons that you can learn from that. If you can, you want to do that when they’re in so they can—this can be a collaborative effort where they can cheat and ask their friends to write that email. But either way, in some cases, if you get too much talent, you can have this as a homework, kind of filter out people that are totally not right for the job from other people.

But, yeah, you want to have them pitch you. You want to have them write a cold email, do some research and explain their thinking. And then you’re ultimately going to have to make a judgment call, but you will never know until you have them do the job.

Why you should do a 30-day trial period before giving someone a full-time job offer

So, one of the reasons—or one of the lessons we learn out of that is that for most sales jobs, we never offer somebody full-time employment for our sales job. We would always do a contract first, 30 days trial period where you can trial out our company, do you really like this job and working with us? And we can trial you and see are you really the right fit for this job. We’d always do a 30- day trial period before giving somebody a full-time job offer. I know that in Europe and other places, that might be difficult and you might have to find more creative ways around it, but I would always test before giving somebody a full-time job on this because you never know until you see them.

How do they perform day in, day out? Are they consistent? How do they do when they have a bad day? How do they do when they have a good day? Right? All these things are things you need to see before you really can judge somebody as a salesperson. All right. I’m not going to talk about this too long.

What type of traits should you look for in salespeople?

What to avoid: Wolves and lambs

What kind of person are we looking for when we’re looking for ideal sales talent? I really think that the salesperson of the future is not the salesperson of the past. So, the people that were amazing at selling in the past where they’re kind of Wolf of Wall Street’s, the unfriendly and strong personality types. This is the top left of this quadrant, right?

Unfriendly and strong means “I come from a place where I want to take things away from you so I can gain them. I’m not friendly. I want to crush the competition. I want to kill the competition. I want to destroy everybody. I want to get as much money from people as possible. I’m in it completely selfishly to take away value from people’s pockets and put it in my own. But I also do it not just unfriendly but I do it with strength. I’m aggressive. I’m alpha. I’m super-pushy.” These people traditionally have reined the sales organizations that’s why selling has such a bad name. And these are the people that to a certain degree will always have some type of success. It’s going to be dwindling over the future, but they have success because they are aggressive and people are afraid of them and they are pushing people into decisions that they then later regret.

Now, this model doesn’t work anymore. It does still in some cases, but it works less and less and less, and I predict it will be a declining trend in the future because information is so all- encompassing and especially in today’s world, most products that you don’t buy once in a lifetime and you can never cancel, most of the products, you can change your mind or you can cancel it if it’s a subscription product. And so, unhappy customers are just fucking horrible for your business. So, people that come from a place of unfriendly strength even if they’re super- alpha and aggressive and you think, “No, this guy could sell a lot,” they’re typically very toxic for your business. Don’t hire these people.

The exact opposite—the friendly and weak—those are also not the right people unfortunately, right? If somebody is super-friendly but they’re all weak, they’re all apologetic. You know, when you go to “Boo!” they’re always like “Ahh” get afraid. They’re not going to be able to tell people what to do. They’re not going to be able to really push and hustle. They’re not going to be right for you. They’re not going to be able to convince anybody of anything.

What to look for: Friendly strength

So, what we’re really looking for the sweet spot is the friendly and strong, right? And the best way of thinking about this is thinking about it in a framework of like a good doctor or a great lawyer, somebody that’s a domain expert, somebody that’s an expert. This is a person that ideally wants you to succeed. He wants you to do well. He wants their customers to do well. He wants to create value. But he also comes from a place of strength. He knows better than you. He is an expert in this space. He will tell you what to do. He’s not going to ask you. He’s going to ask you “What is your situation?” He’s going to be very, very empathetic to try to understand everything and anything, get

He’s going to be very, very empathetic to try to understand everything and anything, get perfect context of what is the situation. But once this expert truly understands what’s going on and they prescribe a solution, they’re not debating that solution with you. They’re not wishy-washy, “Maybe you want to do this or maybe not. I’m also not really sure what we should do here.” That’s not what you want to hear from your doctor. You want to hear from your doctor, “All right, we got it. It’s this and here’s the cure. Here’s how we’re going to get to fix this problem for you,” right? We’ve done this before. It works. It’ll work this time as well. So, you’re looking for people that you—just ask yourself “Could this be a good doctor, a good lawyer?” Somebody that has authority, somebody that has strength but is also trustworthy. Look for these types of people because these are going to be the people that are going to be great for you and your sales team.

That’s not what you want to hear from your doctor. You want to hear from your doctor, “All right, we got it. It’s this and here’s the cure. Here’s how we’re going to get to fix this problem for you,” right? We’ve done this before. It works. It’ll work this time as well. So, you’re looking for people that you—just ask yourself “Could this be a good doctor, a good lawyer?” Somebody that has authority, somebody that has strength but is also trustworthy. Look for these types of people because these are going to be the people that are going to be great for you and your sales team.

How to onboard and train salespeople

All right. Few words on onboarding and training salespeople and then a little bit about how to compensate them and then we’re going to go into all your questions. So keep them coming. All right. So, onboarding and training. Again, this is not rocket science, people, right? There’s three basic things you could really do to onboard somebody really quickly—or three basic tactics. Tactic 1 is they can shadow you or other successful salespeople, right? What that means is you—“Hey, this is your first day as a salesperson in our company? Awesome. Sit next to John or Bob or Mary. They’re amazing at this job. They’re doing the job that you need to learn how to And just today or for the next two days, you just sit there and you just observe what they do. You listen to their sales call. You look at how they manage the sales emails. You go with them to sales meetings. You just shadow somebody that’s doing the job.” And this could be the entire day or it could be just, “Hey, we make sure that every day there’s three different salespeople where you’re going to join one sales call or sales meeting, right? So you can see a variety of tactics but you only join when there’s an actual sales conversation going on.” So people could shadow other people when they do the job. You can do

Tactic 1 is they can shadow you or other successful salespeople, right? What that means is you—“Hey, this is your first day as a salesperson in our company? Awesome. Sit next to John or Bob or Mary. They’re amazing at this job. They’re doing the job that you need to learn how to And just today or for the next two days, you just sit there and you just observe what they do. You listen to their sales call. You look at how they manage the sales emails. You go with them to sales meetings. You just shadow somebody that’s doing the job.” And this could be the entire day or it could be just, “Hey, we make sure that every day there’s three different salespeople where you’re going to join one sales call or sales meeting, right? So you can see a variety of tactics but you only join when there’s an actual sales conversation going on.” So people could shadow other people when they do the job. You can do

You can do trainings with them in mock situations, so you do play by plays, right? You do mock calls. “Ring-ring- ring! Hey, I’m Bob.” And then the person has to—you’re still doing the sales conversation, but it’s not a real one. It’s with you for training purposes. Sales meeting, sales conversation, mock emails. “Hey, send me a prospect email—send me an email to get on a demo call,” and then they send the email and then you pretend to be the prospect and you go, “Ahh, I don’t really have time right now.” You go back and forth and you train them on how to send emails, how to make sales calls, how to make sales meetings happen, how to close, how to negotiate. You do mock training sessions with them. And you can do that. Other people on the team can do that, and then you drop them into cold water. You have them do the fucking work. Do the job, but you honestly give them the easy work first. And easy can mean small. It can mean like low-quality leads, smaller leads, leads where you don’t—you’re not—it’s not going to be a make or break. If they mess something up there, if they don’t get something right, it doesn’t matter. It’s not the end of the world, right? We like to get salespeople

Other people on the team can do that, and then you drop them into cold water. You have them do the fucking work. Do the job, but you honestly give them the easy work first. And easy can mean small. It can mean like low-quality leads, smaller leads, leads where you don’t—you’re not—it’s not going to be a make or break. If they mess something up there, if they don’t get something right, it doesn’t matter. It’s not the end of the world, right? We like to get salespeople

We like to get salespeople onboarded as quickly as possible. Do actual selling as quickly as possible. If you’re not a Fortune 500 company, you don’t have like months and months of training people. You have to get them onboarded really, really quickly. And one hack and trick to onboarding somebody effectively especially when you have a really technical product without training them for months and months and months—I mean—and there’s other things you can do, right? I mean they should be signing up for your competition and then have the competitors pitching them on their product. You should have them do all kinds of research. I mean there’s a ton of things that you can do to train people and get them

I mean there’s a ton of things that you can do to train people and get them onboarded, but the main philosophy is do it fast and the main philosophy on the product and technology side is instead of trying to train them to perfection is this 80/20 rule is you want to figure out what other top 10, top 20 questions that most prospects, most customers ask about the product or the technology. You want to write down the answers to these questions and then you want to give this document to your new people to train and onboard them. I’m a big fan of scripts and documentation that helps you onboard and train people really, really well, so make sure that you have a sales call script. Make sure that you have a Q&;A script or like “Here’s the top questions people ask us. Here’s the response that you can give for these.” And then train your new salespeople that if there is a question that they are not sure about or they don’t know the answer to, then they need to say “I don’t know.” Here’s the script for this. Somebody asked a difficult technical question the new sales hire doesn’t know. The answer is “That’s a great question. Honestly, I don’t know the right answer to this and I don’t want to give you false information. Let me get back to you on this. I can go and find the right information and get you the right information. But before I do that, let me ask you, why is this important for you? Why do you need this? In an ideal world, what would be my answer? What would you want us to have? What would you want it to be and why?” Train them to be honest when they don’t know something to just say “I don’t know but I’ll get you the information,” but then train them to ask the right questions, the what it is they want and why so that you have—they have all the context needed when they go back to the team to ask. And then what happens is that the first few weeks, your new sales hires, they will come back often to—they’re going to have tons of questions and every week, it’s going to be less and less and eventually the delta X of product knowledge and technology and industry knowledge just goes away because most prospects will ask the same questions.

And then train your new salespeople that if there is a question that they are not sure about or they don’t know the answer to, then they need to say “I don’t know.” Here’s the script for this. Somebody asked a difficult technical question the new sales hire doesn’t know. The answer is “That’s a great question. Honestly, I don’t know the right answer to this and I don’t want to give you false information. Let me get back to you on this. I can go and find the right information and get you the right information. But before I do that, let me ask you, why is this important for you? Why do you need this? In an ideal world, what would be my answer? What would you want us to have? What would you want it to be and why?” Train them to be honest when they don’t know something to just say “I don’t know but I’ll get you the information,” but then train them to ask the right questions, the what it is they want and why so that you have—they have all the context needed when they go back to the team to ask. And then what happens is that the first few weeks, your new sales hires, they will come back often to—they’re going to have tons of questions and every week, it’s going to be less and less and eventually the delta X of product knowledge and technology and industry knowledge just goes away because most prospects will ask the same questions.

Here’s the script for this. Somebody asked a difficult technical question the new sales hire doesn’t know. The answer is “That’s a great question. Honestly, I don’t know the right answer to this and I don’t want to give you false information. Let me get back to you on this. I can go and find the right information and get you the right information. But before I do that, let me ask you, why is this important for you? Why do you need this? In an ideal world, what would be my answer? What would you want us to have? What would you want it to be and why?” Train them to be honest when they don’t know something to just say “I don’t know but I’ll get you the information,” but then train them to ask the right questions, the what it is they want and why so that you have—they have all the context needed when they go back to the team to ask.

And then what happens is that the first few weeks, your new sales hires, they will come back often to—they’re going to have tons of questions and every week, it’s going to be less and less and eventually the delta X of product knowledge and technology and industry knowledge just goes away because most prospects will ask the same questions.

3 ways to organize your sales team

All right. A few quick words on how to structure the sales team, again, there’s three simple structures. There’s the all-you-can-eat-all-in-one structure where basically every salesperson is their own sales team. They have to do the lead generation themselves. They have to prospect themselves. They have to do the qualifying themselves, the closing themselves. They have to do A to Z everything on their own. They get zero support. They just have to figure out everything on their own and that’s the island structure. That’s one way of organizing a sales team.

There’s the assembly line. Assembly line is basically you have different teams and you build expertise and structures around these teams. So you have the lead generation team, then you have the SDR team, you know, the team that’s generating leads and qualifying them. You have the account executive team. Those are the people that are the closers and then you have the success team. Those are the people that they call managers, right? So from generating the lead to qualifying it to closing it to servicing it, you have a different person doing their job, different teams and every lead is being pushed through the assembly line down the assembly line from the top of the funnel to the bottom of it. That’s one way of structuring your sales team. And then the last way of structuring your sales team is in pods. Pods are basically instead of having this SDR team and then having the closer team and then having the success team, what you have is you have these pods that are like one lead generation person, one qualifying person or two qualifying people, one closer or two closers and one success person. So, you have pods, the teams that have all key functional responsibilities in one group so that every customer that’s being acquired by that group is owned within the group. The lifecycle of the entire customer doesn’t pass on in the future. It stays

And then the last way of structuring your sales team is in pods. Pods are basically instead of having this SDR team and then having the closer team and then having the success team, what you have is you have these pods that are like one lead generation person, one qualifying person or two qualifying people, one closer or two closers and one success person. So, you have pods, the teams that have all key functional responsibilities in one group so that every customer that’s being acquired by that group is owned within the group. The lifecycle of the entire customer doesn’t pass on in the future. It stays within the pot. Each and every one of these three structures

Each and every one of these three structures have pros and cons. In the technology and startup world, you almost never see the all-in- one structure anymore. It’s mostly a battle between assembly lines and pods. There’s pros and cons in both of them. Pods are better because typically you have much more collaborative efforts. You have much more—a high level of empathy and understanding on each and every level of the person who’s doing lead gen understands everything that the success person has to do. So, the quality of work is usually a lot better. The collaboration method is a lot better. The empathy, the cultural level is a lot better, a lot more friendly, and the customer experience oftentimes can be much better. So those are the pros versus the assembly line. The cons versus the assembly line on the

The cons versus the assembly line on the pot structure and vice versa, the pro on the assembly line structure is that you typically have a lot less competition in each function and with that less skill and expertise. So, the closer—if you have a team full of closers, then they are going to push themselves to become better and better and better. They’re going to see what other people do in the closing team. Just that natural—that competition is going to breed excellence. If you’re the only closer or if it’s you and one other closer in your little pot of other people, you’re going to have less of that push by excellence, less of that friendly competitive structure, less of like real positional expertise, right? So, depending on the market you’re in, depending on how aggressive you have to be, either the assembly line or the pod structure is a better structure, but all three are basic available structures on how to organize your sales team. And all of them are available—I will say that right now in the valley, I would say it’s about a 50-50 split between assembly lines and pods just to give you guys some benchmarking. So, there’s really

And all of them are available—I will say that right now in the valley, I would say it’s about a 50-50 split between assembly lines and pods just to give you guys some benchmarking. So, there’s really no thing that’s better than the other. It really depends on your company, your culture and your market, how you want to do that.

How to compensate salespeople

All right. So, few final words on how to pay these new people and all these sales hires and then we’ll go into Q&A finally. So, again, keep the questions coming. All right. So, compensation structures, well, a few words on compensation. Number one, don’t overthink this. You have to think about—no, let me get to that in the next slide. So, the components of compensation structures. Let’s start with the ABCs here. So, you can pay a base salary. This is something that is guaranteed no matter what the person does as long as they show up, they get this base. There’s commission, and

There’s commission, and commission can both be a percentage of revenue but it can also be just a fixed dollar amount. So, you know, in most B2B scenarios, you’re going to have some kind of a percentage, so every time you close a deal, you get X percent of the deal size. But there’s industries—so there’s ways where you could say, “Hey, fore every deal you bring in, you get, you know, whatever, $100, $200” or “For every—” especially in the SDR space, it could be easier to say, “Hey, every lead you—every qualified lead or every demos scheduled gets you $200, $100,” whatever it is, some fixed amount. That has nothing to do with how big the deal is going to end up being at the end.

So, you have a base. You have a commission. You have bonus structure. So, bonus and commission are fairly similar, but they’re not the same. Commission is very transactional and it’s very related. “I did this one demo so I got this one little piece of money.” A bonus can be—is usually more of a bigger chunk of money that comes less regularly and that comes even more accumulative. So, every quarter, we pay out a bonus for maybe the best performer on the sales team, right? That has nothing to do with the amount of deals you closed or—it’s not a percentage of your deals. It is a reward for being the best of all of them. Or, if the overall company, if we accomplish this revenue goal, everybody on the sales team gets a certain bonus. So, bonus can be the kind of more flexible, more related. And then there is

And then there is as a fourth compensation component, they are benefits and other things that you could do. Obviously, you could—you cannot just pay people with money. You could pay salespeople in, you know, getting a lease car or getting a cellphone or smartphone and the bill paid for. You could pay them in getting trainings and really expensive seminars paid for, weekend trips. There’s all kinds of things you could pay people in that are not pure cash in their bank account. So, you have to consider all components as ways to compensate for your sales team.

Now, when it comes to like coming up with a compensation structure, I really want all of you to have an MVP state of mind when it comes to that. You want to have a minimum viable—an MVC in this case—a minimum viable compensation structure. First of all, start ASAP. Most people try to come up with the perfect compensation structure before they announce it. There is no such thing as a perfect compensation structure. A compensation structure is a living, breathing, changing

A compensation structure is a living, breathing, changing thing and it will always have to keep evolving as your business, your market, your industry is evolving and changing. It sucks but it’s just one of these truths. It’s just like with a product, you’re never just going to have the perfect and then you never have to touch it again. You’re going to have to constantly reinvent, change, make additions, make updates. And the same thing is true for compensation structures. So, don’t wait for the perfect time or when you have the perfect formula. Just start ASAP. Start simple. Start very, very basic and then start with an open mind that you’re probably going to screw it up in version 1. You’re going to have to change it. You’re going to have to tell your people about this. This is part of being—it’s part of the fun of being a salesperson in a startup. If you want to have a compensation structure that is set in stone, go to IBM, right? Go to Oracle. Go to some large organizations

So, don’t wait for the perfect time or when you have the perfect formula. Just start ASAP. Start simple. Start very, very basic and then start with an open mind that you’re probably going to screw it up in version 1. You’re going to have to change it. You’re going to have to tell your people about this. This is part of being—it’s part of the fun of being a salesperson in a startup. If you want to have a compensation structure that is set in stone, go to IBM, right? Go to Oracle. Go to some large organizations that’s been around forever. If you want to be at a startup, change means also that some things are going to be in fluid motion when it comes to your payment. So, compensation structure. Start really fast and then there’s really two ways to go about and you can do it collaboratively. You could tell people honestly, “Hey, we don’t have the perfect compensation structure yet for this job. I want to come up with the right compensation structure with you and we have to keep in mind this is not just about how we are going to get money, but this is about how the people we’re going to be hiring are going to be making money and how this company is going to scale. So we really need to figure out a compensation structure that’s going to incentivize all the right things and it’s going to be really scalable for the business. And the cool thing is you are going to have input on this. We’re going to do this together. You can be very collaborative and many Silicon Valley startups do that. Or, you can take the other approach, is get more aggressive. It’s the fake it until you make it one.

So, compensation structure. Start really fast and then there’s really two ways to go about and you can do it collaboratively. You could tell people honestly, “Hey, we don’t have the perfect compensation structure yet for this job. I want to come up with the right compensation structure with you and we have to keep in mind this is not just about how we are going to get money, but this is about how the people we’re going to be hiring are going to be making money and how this company is going to scale. So we really need to figure out a compensation structure that’s going to incentivize all the right things and it’s going to be really scalable for the business. And the cool thing is you are going to have input on this. We’re going to do this together. You can be very collaborative and many Silicon Valley startups do that. Or, you can take the other approach, is get more aggressive. It’s the fake it until you make it one.

Or, you can take the other approach, is get more aggressive. It’s the fake it until you make it one. Is you talk to a few people that have up commission structures before. You take the best first guess and create a version 1 of that for your business. You cross your fingers. You hope it works, and if it doesn’t, you have to change it. And if that pisses off your sales team, you have to get rid of them and hire new salespeople, right? It’s a much more aggressive approach where you pretend this is the commission structure and it works perfectly. There’s no doubt about it. You’re going to be making this amount of money and then if it doesn’t work out, you go, “You know what? We screwed up. I’m sorry. We’re going to have to start again. And if that’s too much of a hassle and if you’re really pissed, go find a job that’s more stable.” And you go and hire new people. This is much more of an aggressive approach. I’ve seen startups do this and do this successfully. It’s a question of ethics. It’s a question of style and culture and this is not for everybody. But these are the two. You can either do it with your sales team or you could pretend that you figured it out alone and you can pretend that this is the right compensation structure. And then if it’s not, you’re going to have to deal with some trouble and the trouble typically means that people are going to be really pissed if you changed around the compensation structure especially when you have to lower it or take it away in certain parts where it’s just not feasible. And sometimes that means that you have to part ways with people because they’re never going to get over that.

It’s a much more aggressive approach where you pretend this is the commission structure and it works perfectly. There’s no doubt about it. You’re going to be making this amount of money and then if it doesn’t work out, you go, “You know what? We screwed up. I’m sorry. We’re going to have to start again. And if that’s too much of a hassle and if you’re really pissed, go find a job that’s more stable.” And you go and hire new people. This is much more of an aggressive approach. I’ve seen startups do this and do this successfully. It’s a question of ethics. It’s a question of style and culture and this is not for everybody. But these are the two. You can either do it with your sales team or you could pretend that you figured it out alone and you can pretend that this is the right compensation structure. And then if it’s not, you’re going to have to deal with some trouble and the trouble typically means that people are going to be really pissed if you changed around the compensation structure especially when you have to lower it or take it away in certain parts where it’s just not feasible. And sometimes that means that you have to part ways with people because they’re never going to get over that.

Q&A

When do you need hunters versus farmers?

All right. There’s a million more things to be said about all these charts, but that’s why we do Q&A. All right. So, finally, let me get to your questions and you can keep the questions coming as I’m scrolling through them and trying to answer them as good as I can one by one. All right. Let me take a look at this. So, one question was “When do you need hunters versus farmers?” So, another way of saying hunter or farmer, a hunter is basically somebody that’s prospecting and closing and a farmer is typically somebody that is account managing, right? Somebody that’s keeping the relationship and making sure that the relationship grows. But it depends on your market. If you do enterprise sale like it depends on your market and maturity of the business that you’re in, but typically you need both, right? You will always need both and one way or another, you’ll need people that bring you business in and then you’re going to need people that keep that business. Today, we call the people that keep a business success managers. You know, a few years ago, they would be called account managers. But it’s basically the same—it’s like a person that is building and keeping a relationship with our customers so that our customers keep spending more money with us. And every time we have a new product or there’s a renewal of contract, that customer stays and expands their business with us. And you will always need both. What is more important depends on the stage of your company and where you’re at. At the beginning, you’re going to have to be both in one way or another. And also, you’re going to probably have to hire some people that are capable of doing both before you start specializing people too fast.

So, one question was “When do you need hunters versus farmers?” So, another way of saying hunter or farmer, a hunter is basically somebody that’s prospecting and closing and a farmer is typically somebody that is account managing, right? Somebody that’s keeping the relationship and making sure that the relationship grows. But it depends on your market. If you do enterprise sale like it depends on your market and maturity of the business that you’re in, but typically you need both, right? You will always need both and one way or another, you’ll need people that bring you business in and then you’re going to need people that keep that business. Today, we call the people that keep a business success managers. You know, a few years ago, they would be called account managers. But it’s basically the same—it’s like a person that is building and keeping a relationship with our customers so that our customers keep spending more money with us. And every time we have a new product or there’s a renewal of contract, that customer stays and expands their business with us. And you will always need both. What is more important depends on the stage of your company and where you’re at. At the beginning, you’re going to have to be both in one way or another. And also, you’re going to probably have to hire some people that are capable of doing both before you start specializing people too fast.

Today, we call the people that keep a business success managers. You know, a few years ago, they would be called account managers. But it’s basically the same—it’s like a person that is building and keeping a relationship with our customers so that our customers keep spending more money with us. And every time we have a new product or there’s a renewal of contract, that customer stays and expands their business with us. And you will always need both. What is more important depends on the stage of your company and where you’re at. At the beginning, you’re going to have to be both in one way or another. And also, you’re going to probably have to hire some people that are capable of doing both before you start specializing people too fast.

What is more important depends on the stage of your company and where you’re at. At the beginning, you’re going to have to be both in one way or another. And also, you’re going to probably have to hire some people that are capable of doing both before you start specializing people too fast.

How should you expand sales in international markets?

All right. Next question, “So, if a company had success in Europe and is now trying to enter in the really important market of—like a new and important market like let’s say the U.S. or Latin America, is it still a good idea to go through step 1, 2 and 3?” Yeah, I would say so. That’s a good question. But I would definitely say so if I’m having tremendous success in the U.S. and now I say “We want to enter the Japanese market.” I am not just going to hire some Japanese person that has a lot of experience in selling and go “Here’s what we did in the U.S. You have a lot of experience in Japan. Best of luck. I’m sure you’re going to crush it.” Not to say that I would go to Japan and try to do it myself, but I would still go over there to Japan and say, “You know what, in the next 6 months, I’m going to live in Japan. I’m going to try to hire a few Japanese people with experience, get some advisers and I’m going to try to be involved in every step of the way to see what’s going on, to try to learn about that market, to try to understand if what they’re doing makes sense or not.” You really have to immerse yourself. And then, yeah, like—so, you might have to merge step 1, 2 and 3 a little bit, but you still have to be really hands-on. I would absolutely advise on that, yeah.

Not to say that I would go to Japan and try to do it myself, but I would still go over there to Japan and say, “You know what, in the next 6 months, I’m going to live in Japan. I’m going to try to hire a few Japanese people with experience, get some advisers and I’m going to try to be involved in every step of the way to see what’s going on, to try to learn about that market, to try to understand if what they’re doing makes sense or not.” You really have to immerse yourself. And then, yeah, like—so, you might have to merge step 1, 2 and 3 a little bit, but you still have to be really hands-on. I would absolutely advise on that, yeah.

And then, yeah, like—so, you might have to merge step 1, 2 and 3 a little bit, but you still have to be really hands-on. I would absolutely advise on that, yeah.

When can you determine whether you’ve hired the right salesperson or not?

All right. Next question, “For companies with sales cycles that are 3 to 6 months, let’s say, how can you quickly decide if the salesperson is working or not?” Yeah, it’s a really great question. When—in most jobs, you’re not going to know how great they are closing in the first few weeks because they’re not going to be closing anything. So, what you’re going to have to do is you’re going to have to judge them on all the steps that come before the close. And it’s going to have to be—it might have to be just a qualitative judgment call versus a quantitative one, right? So, you know, you’re going to—so let’s say somebody has to prospect and close, but the closing cycle takes 6 months, what you have to judge them on is how well do they prospect and you’re going to join them in their per sales call and judge them how well did they do the first call? You’re going to judge them on how good are they doing on the follow-up? How aggressive are they on managing the objections that the customer had? How good are they in preparing the next call? Like, you’re going to look for all these little clues where they get—when somebody tells them no, what do they do? You’re going to have to judge them on different clues than just how much revenue the person bring in because it takes too much time for that number to manifest itself, so you have to look for other things to judge people on. It’s as simple as that. It’s not

You’re going to judge them on how good are they doing on the follow-up? How aggressive are they on managing the objections that the customer had? How good are they in preparing the next call? Like, you’re going to look for all these little clues where they get—when somebody tells them no, what do they do? You’re going to have to judge them on different clues than just how much revenue the person bring in because it takes too much time for that number to manifest itself, so you have to look for other things to judge people on. It’s as simple as that. It’s not perfect science, but you’re going to have to make a judgment call. Do I think this person can close this deal or not? And if you don’t think so, you’re going to have to wait for 6 months to know for certain it didn’t happen. You have experience in this. You’ve seen deals close. You can just judge them on all the early signs of how they deal with things on a day-to- day. Yeah, that’s really it. That’s the best you can do. It’s

And if you don’t think so, you’re going to have to wait for 6 months to know for certain it didn’t happen. You have experience in this. You’ve seen deals close. You can just judge them on all the early signs of how they deal with things on a day-to- day. Yeah, that’s really it. That’s the best you can do. It’s a great—it’s an excellent question. Next. And let me know if I answered it—by the way, if any question—if any answer I give is not clear enough or you want even more information, just follow up with more questions in chat. I’ll go through them. All right. Next question. Let me scroll here. “When we were selling to supermarkets, we found a school where supermarket managers were educated. We got in touched and started hiring. Very good experience because they understood our client’s problems right away and we’re really thankful for an opportunity outside the normal culture.” So find that interesting talent pool to hire from. “Well, we hired two people there.” Okay. All right. Oh, that’s just an example. It’s not even a question. Awesome example.

Next. And let me know if I answered it—by the way, if any question—if any answer I give is not clear enough or you want even more information, just follow up with more questions in chat. I’ll go through them. All right. Next question. Let me scroll here. “When we were selling to supermarkets, we found a school where supermarket managers were educated. We got in touched and started hiring. Very good experience because they understood our client’s problems right away and we’re really thankful for an opportunity outside the normal culture.” So find that interesting talent pool to hire from. “Well, we hired two people there.” Okay. All right. Oh, that’s just an example. It’s not even a question. Awesome example.

Let me scroll here. “When we were selling to supermarkets, we found a school where supermarket managers were educated. We got in touched and started hiring. Very good experience because they understood our client’s problems right away and we’re really thankful for an opportunity outside the normal culture.” So find that interesting talent pool to hire from. “Well, we hired two people there.” Okay. All right. Oh, that’s just an example. It’s not even a question. Awesome example.

Can you teach salespeople to be friendly and strong?

Question now. “Can you teach weak people to be strong? Or can you teach unfriendly people to be friendly? Or is it personality?” That’s such a great question. I love it. I’m not going to tell you what you can or cannot do, and I’m not going to tell you that people cannot change because I think they can. But I am not going to attempt to teach a weak person to be strong. I’ve tried this many, many, many—I’ve tried this a shit ton of times, never with success. If somebody is weak, teaching them to be strong is a very hard thing. It’s not impossible, but it’s very hard. It needs you to be perfect, them to be perfect. The moment needs to be perfect, the timing. A lot of things have to come together for that to work. In most cases, it’s just not going to work and it’s going to take so much time and energy from you and from them and it’s still not going to result

If somebody is weak, teaching them to be strong is a very hard thing. It’s not impossible, but it’s very hard. It needs you to be perfect, them to be perfect. The moment needs to be perfect, the timing. A lot of things have to come together for that to work. In most cases, it’s just not going to work and it’s going to take so much time and energy from you and from them and it’s still not going to result into anything successful. So, if somebody is weak, I don’t want to be in the business of making them strong. And if somebody is unfriendly, fuck them. Honestly, it’s the no-asshole rule. If somebody is an asshole, fuck them. That’s even like with weak people, I have a soft spot because these are great people and I want them to be strong, so that’s why I’ve attempted to teach weak people to be strong so many times. But with unfriendly people, fuck them. I don’t have any desire to teach them to be friendly. So, no, if somebody is an asshole, they can go. If somebody is weak, I’m sorry but they have to go. That’s my approach at least to this.

So, if somebody is weak, I don’t want to be in the business of making them strong. And if somebody is unfriendly, fuck them. Honestly, it’s the no-asshole rule. If somebody is an asshole, fuck them. That’s even like with weak people, I have a soft spot because these are great people and I want them to be strong, so that’s why I’ve attempted to teach weak people to be strong so many times. But with unfriendly people, fuck them. I don’t have any desire to teach them to be friendly. So, no, if somebody is an asshole, they can go. If somebody is weak, I’m sorry but they have to go. That’s my approach at least to this.

Would you outsource sales overseas?

Next question. “Would you hire overseas contract just for sales? If so, how would you check their skills?” I don’t know, man. I mean this is one of these things that’s like “Hey, I want—” as the example earlier, I want to get into the Japanese market. I’m just going to hire a contract in Japan.” This is such a hard thing to do well. The chances of this not working are astronomical. It’s like can you win the lottery? Yes. But should that be your strategy for how to become rich? Probably not. So, I’m very skeptical on overseas contractors. If you really, really have to do it, you would want to do a shit ton of Skype calls. If you can, you would want to have them travel to you and spend two weeks at your office or you travel to them and spend two weeks with them. If you can’t do that, do lots of Skype calls with video to see them. Have them record their calls so you can listen to them. Have them have access to the email account that they’re using for your business so you can see everything and track everything that’s going on to really know what’s. But I’m not excited about overseas contractors.

If you can’t do that, do lots of Skype calls with video to see them. Have them record their calls so you can listen to them. Have them have access to the email account that they’re using for your business so you can see everything and track everything that’s going on to really know what’s. But I’m not excited about overseas contractors.

Is it a red flag if someone previously worked at a big company or job hops a lot?

Next question. “Is it always a red flag if someone worked previously at big companies like Salesforce or LinkedIn? But worked in all such companies less than one year.” Yeah. I mean it’s definitely—that’s a great question. So, it’s definitely a red flag. Red flag does not mean that this person should work for you or that this person isn’t amazing. A red flag is just something that needs to be paid attention to, something that you need to learn more about. So if I look at somebody’s resume and I see the past 5 companies he worked at and it’s all like 6 months, 12 months, 9 months, 8 months, 7 months. That’s a red flag. So, that makes me very, very skeptical and I will bring it up. The first thing I’ll say is “Hey, dude, why can’t you keep a job? Or why are you leaving jobs everywhere? Give me a good explanation.” I’ll just right out tell people, “What’s wrong with you?” And most of the time, they will give you an explanation, but then the judgment that I have

So if I look at somebody’s resume and I see the past 5 companies he worked at and it’s all like 6 months, 12 months, 9 months, 8 months, 7 months. That’s a red flag. So, that makes me very, very skeptical and I will bring it up. The first thing I’ll say is “Hey, dude, why can’t you keep a job? Or why are you leaving jobs everywhere? Give me a good explanation.” I’ll just right out tell people, “What’s wrong with you?” And most of the time, they will give you an explanation, but then the judgment that I have

And most of the time, they will give you an explanation, but then the judgment that I have is is the explanation really fucking good? Or is it whatever? If they’re like, “Yeah, you know, that’s a good point and I agree and I can also see how that would appear that way. But it was really just circumstances in this company. I did a really good job and I really loved it, but then my boss switched and since I’m really attached to that boss, that other company gave me an offer and then that was the reason why I switched. That company was a new startup and they’re really messed up, so I really hated what they were doing, so I was ready to find something else. And this other company—” If they have an excuse explanation for everything, that doesn’t make—that makes sense but in accumulative still doesn’t explain the problem, I’m going to shy away and not hire them. If somebody tells me outright, “You know what, dude, you’re right. For the past 4 years, I’ve been fucking around. Whenever a job got too easy, I got bored. Or whenever I was offered more money, I left. This looks shitty on my resume for good reasons. I think those were poor decisions in hindsight but that’s what it was. I’ve done this for long enough. I’m ready now to change.” They say that. It doesn’t mean that they’re not going to want to leave 6 months from

If somebody tells me outright, “You know what, dude, you’re right. For the past 4 years, I’ve been fucking around. Whenever a job got too easy, I got bored. Or whenever I was offered more money, I left. This looks shitty on my resume for good reasons. I think those were poor decisions in hindsight but that’s what it was. I’ve done this for long enough. I’m ready now to change.” They say that. It doesn’t mean that they’re not going to want to leave 6 months from now, like that’s a real risk. But at least—I’m like “All right. At least this guy is real—or gal. At least this person is self-aware. He seems to be honest. Do I want to take a risk or not?” But it’s always a red flag for sure. Somebody that can’t stay at a job for an extended period of time, that’s not a good thing.

Should you test senior sales candidates during the interview process?

Next question. “When you’re looking for someone—for a sales director or VP position, is it a great idea to ask ‘Can I give you some homework or test task?’ For example, do some kind of role play sales test to see how candidates will try to sell you on the product, qualify and all that, or prepare a brief sales strategy for our company?” For more senior sales hires, it all depends. It depends. If you’re recruiting them, if I am the VP of sales at LinkedIn and you’re reaching out to me, you’re not going to be able to give me homework, right? Because you’re trying to sell me I should join your company. If I apply, maybe, but it depends on how senior the person is. If the person is super-senior, a VP of sales

If you’re recruiting them, if I am the VP of sales at LinkedIn and you’re reaching out to me, you’re not going to be able to give me homework, right? Because you’re trying to sell me I should join your company. If I apply, maybe, but it depends on how senior the person is. If the person is super-senior, a VP of sales of Microsoft, you don’t want that person to do mock calls with you because they’re not—they don’t have to be good at selling. They don’t have to be good at sales at all. The VP of sales is to not be good at selling at all. Their job is totally different. It’s like the chief technology officer doesn’t have to be a great designer or great at UI or gain dynamic or anything. Their skillset is a totally different one. The VP of sales needs to be great at scaling large sales organizations. They need to be an amazing manager. They need to be good at structuring things, setting processes in place, all that stuff. Not mock-calling you. So, it

They don’t have to be good at sales at all. The VP of sales is to not be good at selling at all. Their job is totally different. It’s like the chief technology officer doesn’t have to be a great designer or great at UI or gain dynamic or anything. Their skillset is a totally different one. The VP of sales needs to be great at scaling large sales organizations. They need to be an amazing manager. They need to be good at structuring things, setting processes in place, all that stuff. Not mock-calling you. So, it depends. Yeah, you definitely want to have really in-depth and deep conversation. You definitely want to give them some challenges you have and see how they think about them and how they would solve these challenges. And not a crazy idea to have them pitch you something, right? To see if they’re good at selling, but it all

Yeah, you definitely want to have really in-depth and deep conversation. You definitely want to give them some challenges you have and see how they think about them and how they would solve these challenges. And not a crazy idea to have them pitch you something, right? To see if they’re good at selling, but it all depends. Do they come to you? Have you tried to recruit them? That changes how much they have to sell themselves to you and how much work they’re going to be willing to do versus how much you have to sell them on your company and the opportunity vice versa.

What stock options should startups offer sales candidates to compete with other startups?

All right, next question. “What stock options should startups offer sales candidates to compete with other startups on the market in Silicon Valley or New York City? Please share your vision both about senior and junior candidates.” So stock options are a tricky thing. Most companies are—traditionally, salespeople were not the type of people that get a lot of stock options so equity in general in startups. Now, because the market has gotten a lot more competitive and salespeople also more valued today at startups, they do. I can’t really give you a general answer to this because it really depends on how early it is. Are we talking about your first two salespeople? Are we talking about your first sales manager? Or are we talking about your hundredth salesperson hire, right? So, you have to think about—sales and marketing are kind of related. You have to think about comparatively what a marketing person will get depending on their seniority. If they’re super-junior, if you’re the founder and you hired three super-junior salespeople that have zero sales experience, you might not have to give them any stock options in their early days. Or maybe just, you know, something very, very small. We’re talking small, not 1%, 2%, 3%. Those are the percentages that you give out to, you know, VPs of sales maybe. Even that person, maybe not. You give out to your first two hires that are very senior. But when it’s super-junior and it’s a job that is not as high in demand, it’s not like your first really—the first engineer versus your first salesperson, then they’re going to have different compensation structures. But it really depends so much on your competition, on your market, on your stage. Honestly, I have a tough time giving you a number. You can email me. Send me an email [email protected] Tell me a little bit more about your company and then I can give you a bit more complete advice there.

I can’t really give you a general answer to this because it really depends on how early it is. Are we talking about your first two salespeople? Are we talking about your first sales manager? Or are we talking about your hundredth salesperson hire, right? So, you have to think about—sales and marketing are kind of related. You have to think about comparatively what a marketing person will get depending on their seniority. If they’re super-junior, if you’re the founder and you hired three super-junior salespeople that have zero sales experience, you might not have to give them any stock options in their early days. Or maybe just, you know, something very, very small. We’re talking small, not 1%, 2%, 3%. Those are the percentages that you give out to, you know, VPs of sales maybe. Even that person, maybe not. You give out to your first two hires that are very senior. But when it’s super-junior and it’s a job that is not as high in demand, it’s not like your first really—the first engineer versus your first salesperson, then they’re going to have different compensation structures. But it really depends so much on your competition, on your market, on your stage. Honestly, I have a tough time giving you a number. You can email me. Send me an email [email protected] Tell me a little bit more about your company and then I can give you a bit more complete advice there.

Even that person, maybe not. You give out to your first two hires that are very senior. But when it’s super-junior and it’s a job that is not as high in demand, it’s not like your first really—the first engineer versus your first salesperson, then they’re going to have different compensation structures. But it really depends so much on your competition, on your market, on your stage. Honestly, I have a tough time giving you a number. You can email me. Send me an email [email protected] Tell me a little bit more about your company and then I can give you a bit more complete advice there.

How should you handle an employee transitioning from sales to success?

All right. Next question. Well—so, somebody is asking about a person on our team moving from a sales position to a success position. That person is much more than a salesperson. That person is kind of—is senior executive in the revenue department. So, it might be that that person will lead the marketing team one day. It might be that the person will lead the success team one day. Today, that person leads a success team because he both knows our customers better than anybody else and knows the product better than anybody else, but also because the success team is a new team that we are designing and organizing and building other companies, so when you want the most senior person to be in the trenches and do this job and help people on it. So that’s kind of the context around this.

Today, that person leads a success team because he both knows our customers better than anybody else and knows the product better than anybody else, but also because the success team is a new team that we are designing and organizing and building other companies, so when you want the most senior person to be in the trenches and do this job and help people on it. So that’s kind of the context around this.

Who should you hire first during an international expansion?

All right, next question. “When a startup already has a product market fit and starts its sales in a new country from scratch, is it a good idea to start the hiring to senior account executives? Divide the company in two parts. Let them sell for two to three months and after that, the person with the best results will become the sales director who would build the rest of the sales team from this moment? All of this is to minimize risk of betting on just one person.” No. So this is not generally a strategy I would advise on how to build a country—or how to build up your sales organization in a country. Being a good salesperson and being an effective sales manager and being a great sales leader like a VP of sales, those are very different things. Somebody can be crushing it, amazing at closing deals and be the worst manager you’ve ever met. Most people actually that are really fucking incredible salespeople are not good managers. They’re not good sales managers. Most of the people that are really fucking incredible sales managers are not the best salespeople. They have different skillsets. So, I don’t think what you want to do is, say, “Hey, two sales guys, sell for three months and whoever sold the most, you’re now the sales manager and you’re taking over the country.” I don’t know. I would be more hands-on and not necessarily approach it this way. I would approach it still the same way that I mentioned at the beginning of the webinar, which is first you do it yourself or you really have a lead involved. If some more junior people, you bring in

No. So this is not generally a strategy I would advise on how to build a country—or how to build up your sales organization in a country. Being a good salesperson and being an effective sales manager and being a great sales leader like a VP of sales, those are very different things. Somebody can be crushing it, amazing at closing deals and be the worst manager you’ve ever met. Most people actually that are really fucking incredible salespeople are not good managers. They’re not good sales managers. Most of the people that are really fucking incredible sales managers are not the best salespeople. They have different skillsets. So, I don’t think what you want to do is, say, “Hey, two sales guys, sell for three months and whoever sold the most, you’re now the sales manager and you’re taking over the country.” I don’t know. I would be more hands-on and not necessarily approach it this way. I would approach it still the same way that I mentioned at the beginning of the webinar, which is first you do it yourself or you really have a lead involved. If some more junior people, you bring in

So, I don’t think what you want to do is, say, “Hey, two sales guys, sell for three months and whoever sold the most, you’re now the sales manager and you’re taking over the country.” I don’t know. I would be more hands-on and not necessarily approach it this way. I would approach it still the same way that I mentioned at the beginning of the webinar, which is first you do it yourself or you really have a lead involved. If some more junior people, you bring in a senior sales—somebody that has done sales management, not somebody that has been an account manager. Somebody that has been a sales manager—sales team manager, then you bring in some big guns. I would do it step-by- step. I would not advise to just have two people selling in the country and whoever sold the most now manages the country. It can work, but not sure that that’s going to be the best way to success here.

I would do it step-by- step. I would not advise to just have two people selling in the country and whoever sold the most now manages the country. It can work, but not sure that that’s going to be the best way to success here.

When would you recommend outsourcing sales to another company?

All right, next question. “When would you recommend to hire a company—to start the sales force? Just like Elastic did for startups.” Never. So—not never, but here’s the thing with outsourcing sales, don’t do it. Here’s the only time that I want you to outsource sales. I want you to outsource sales once you truly have mastered parts of the sales process and you now know that certain parts you’ve mastered and you now know that probably you could outsource it for cheaper or for better quality or for faster. So, lead generation is something that a lot of times get outsourced. Scheduling can be outsourced. Even demos—like certain things in the funnel can be outsourced. But if you don’t know how to do them, you cannot outsource it. I’ll give you an example. I’ll ask you a counter-question. When is the—I want to build a social gaming app. If I now go to a web development company and say, “Hey, I want you guys to build me a social gaming app,” and they go, “Cool. How exactly do we need to build this? What is the idea? What does it need to look like?” And I tell them “I don’t know. I just know I want a million users and I want a social gaming app. Build it.” That’s not going to fucking work. It’s the same thing in selling. You can’t just go to an outsourcing firm and say, “Hey, I have this product and I don’t know how to sell it, but I want you to come up with it.” Believe me, we had hundreds of companies every month approach us asking us this question, and we attempted it with a bunch of customers. We tried to figure it out for them. It’s very tough. I’ve written two blog posts about how to do outsourcing and when you do it, how to manage the process. Just send me an email, [email protected] I’ll share you these posts. They’re much more in-depth and detailed and then we can go back and forth in this. But my general advice to you is the best time to outsource things is when you have mastered them. The reason why we left Elastic is because we launched Close.io and Close.io was a growing significantly faster than ElasticSales, so it was clear that that was a much bigger business. So, we built Close.io as an internal tool at Elastic. We launched it eventually because we thought the product was really cool and then we saw massive growth with Close.io and it was clear that within a year, the software would do more revenue than the services business. So, why do the services business?

I’ll give you an example. I’ll ask you a counter-question. When is the—I want to build a social gaming app. If I now go to a web development company and say, “Hey, I want you guys to build me a social gaming app,” and they go, “Cool. How exactly do we need to build this? What is the idea? What does it need to look like?” And I tell them “I don’t know. I just know I want a million users and I want a social gaming app. Build it.” That’s not going to fucking work. It’s the same thing in selling. You can’t just go to an outsourcing firm and say, “Hey, I have this product and I don’t know how to sell it, but I want you to come up with it.” Believe me, we had hundreds of companies every month approach us asking us this question, and we attempted it with a bunch of customers. We tried to figure it out for them. It’s very tough. I’ve written two blog posts about how to do outsourcing and when you do it, how to manage the process. Just send me an email, [email protected] I’ll share you these posts. They’re much more in-depth and detailed and then we can go back and forth in this. But my general advice to you is the best time to outsource things is when you have mastered them. The reason why we left Elastic is because we launched Close.io and Close.io was a growing significantly faster than ElasticSales, so it was clear that that was a much bigger business. So, we built Close.io as an internal tool at Elastic. We launched it eventually because we thought the product was really cool and then we saw massive growth with Close.io and it was clear that within a year, the software would do more revenue than the services business. So, why do the services business?

It’s the same thing in selling. You can’t just go to an outsourcing firm and say, “Hey, I have this product and I don’t know how to sell it, but I want you to come up with it.” Believe me, we had hundreds of companies every month approach us asking us this question, and we attempted it with a bunch of customers. We tried to figure it out for them. It’s very tough. I’ve written two blog posts about how to do outsourcing and when you do it, how to manage the process. Just send me an email, [email protected] I’ll share you these posts. They’re much more in-depth and detailed and then we can go back and forth in this. But my general advice to you is the best time to outsource things is when you have mastered them. The reason why we left Elastic is because we launched Close.io and Close.io was a growing significantly faster than ElasticSales, so it was clear that that was a much bigger business. So, we built Close.io as an internal tool at Elastic. We launched it eventually because we thought the product was really cool and then we saw massive growth with Close.io and it was clear that within a year, the software would do more revenue than the services business. So, why do the services business?

But my general advice to you is the best time to outsource things is when you have mastered them. The reason why we left Elastic is because we launched Close.io and Close.io was a growing significantly faster than ElasticSales, so it was clear that that was a much bigger business. So, we built Close.io as an internal tool at Elastic. We launched it eventually because we thought the product was really cool and then we saw massive growth with Close.io and it was clear that within a year, the software would do more revenue than the services business. So, why do the services business?

When going from founder-driven sales to founder sales manager, how should you split your time?

All right. Next question. “When going from founder salesperson to founder sales manager, how much time should you dedicate on managing? How much on making sales?” Ah, that’s a nice question. I like that. As a general rule of thumb—so, the way that I would look at this holistically is you want to look at it in a sliding scale. So, at the beginning, you want to still do sales 80% of the time and manage 20%. Then every consecutive week if that’s your timeline, you would want to go down. So you start 80% of your time selling, 20% managing and then you go 70% selling, 30% managing, 60-40, 50-50, and then eventually you want it to be reversed with 20% of your time you’re still selling so you have some idea what’s going on, but the majority of your time you’re managing.

So, at the beginning, you want to still do sales 80% of the time and manage 20%. Then every consecutive week if that’s your timeline, you would want to go down. So you start 80% of your time selling, 20% managing and then you go 70% selling, 30% managing, 60-40, 50-50, and then eventually you want it to be reversed with 20% of your time you’re still selling so you have some idea what’s going on, but the majority of your time you’re managing.

Can you give an example of a short testing period?

All right. Next question. “Can you give an example of a short testing period? For example, two weeks to one month.” What exactly do you mean by giving an example? Example of how long it should be because you’re already saying two to one month. Tell me a little bit more. Do you want to—do you mean—elaborate on what a salesperson would have to do in those two to four weeks? Just let me know in the comments and I’ll answer it. But I’m not quite sure what you want to know. I’ll continue with the next question in the meanwhile.

How to transition from selling someone on working for you to having them sell you on hiring them

All right. “Hiring. When you reach out to someone you want to hire, you’re first selling to them. How do you make the transition within the interview to make them sell to you? Or would you do your selling and his selling on separate meetings? How to tackle this?” It’s a great question. Yeah, I’m definitely—it depends like most things, but first I want to sell you and once you’re sold, now I want you to sell me and the way that—this could be in two separate calls or it could just be in the middle of a call where—or it could be just that I structure the call where I say, “Hey listen, let’s try to figure out if this is a good fit. Let me tell you a bit about us, what we’re doing, why what we’re doing is important, what we’re looking for, what’s going on in our lives. And then I’d love to learn a little bit more about you, how are you, what is driving you, what are you trying to accomplish in the next few years in your career, what are you really thriving at, what are you most interested in, and then we’ll take the information that we share and we’ll keep going and exploring if this is a good fit or not.” It’s very organic. Once the person—once I say, “Tell me a little bit more about your background. How did you get into sales or how did you get into doing this or that? What are you trying to do next? What’s long-term? What do you want to do?” As they’re giving me the answers, I’ll ask one more question and that’s basically where they’re selling themselves or they’re giving me the information would either be sold or not sold on that.

Yeah, I’m definitely—it depends like most things, but first I want to sell you and once you’re sold, now I want you to sell me and the way that—this could be in two separate calls or it could just be in the middle of a call where—or it could be just that I structure the call where I say, “Hey listen, let’s try to figure out if this is a good fit. Let me tell you a bit about us, what we’re doing, why what we’re doing is important, what we’re looking for, what’s going on in our lives. And then I’d love to learn a little bit more about you, how are you, what is driving you, what are you trying to accomplish in the next few years in your career, what are you really thriving at, what are you most interested in, and then we’ll take the information that we share and we’ll keep going and exploring if this is a good fit or not.” It’s very organic. Once the person—once I say, “Tell me a little bit more about your background. How did you get into sales or how did you get into doing this or that? What are you trying to do next? What’s long-term? What do you want to do?” As they’re giving me the answers, I’ll ask one more question and that’s basically where they’re selling themselves or they’re giving me the information would either be sold or not sold on that.

Once the person—once I say, “Tell me a little bit more about your background. How did you get into sales or how did you get into doing this or that? What are you trying to do next? What’s long-term? What do you want to do?” As they’re giving me the answers, I’ll ask one more question and that’s basically where they’re selling themselves or they’re giving me the information would either be sold or not sold on that.

What would be the best training technique for a sales team?

Next question. “What would be the best training technique for a sales team in case of internal and external?” Best way to train—so, well, there’s a few ways that you can train people. Salespeople can read books or watch seminars or talks in sales. YouTube has like a million hours of sales training free. Have your sales team get some good ones. You know, we have tons of sales material, sales workshop stuff out there. Get some good ones. 

Give them things to watch. Give them things to read. Give them—practice with them in mock situations. So every hard training, easy fight. Every day have your sales team do mock trainings with each other. Cold calls, ring-a- ring, “Hey, I’m Bob. Hey, I’m Jenny” and then give feedback to each other on what they did well, what they didn’t do well. So training in mock situations with feedback. Have them record their calls, record their sales conversation and then listen to them and then critique themselves, analyze themselves. 

The best way to learn and grow is to self-reflect. So have your salespeople watch themselves, listen to themselves, analyze themselves and improve on that. And then expose them to excellent, like have them see other people that do really fucking amazing. Have them join you when you do a sales call, when you do some kind of a big sales negotiation meeting, and have them learn from you. Those are really all the ways and all it really needs.

How should the founder manager evaluate new hires?

All right. Yeah, “basic framework of what the founder manager would evaluate.” During the trial period? Well, four weeks, let’s say I hire somebody junior to do prospecting work, so first week I would just judge them on things that are cultural and that are just fundamental. Is this person showing up on time? Is this person constantly watching the clock to when they can go home? Or is this person just naturally want to stay longer, do more and seems to be excited about the work? Is this person asking lots of questions? Is this person trying to connect with other people in the company? Is this person coming up with ideas? Is this person energetic? What happens when I give critical feedback or when I critique this person? Is this person coachable? Is this person fun to be around? Do I like this person? Like you just judge on these basic things. Does this person seem to be learning, like when I tell them something about our product, does this person seem smart and seem to be learning fast? Or is this person learning really, really slowly? So I’ll touch on all these things in the first week. And then the—The first week, you just want them to be showing up, learning the ABCs, meeting the people, getting comfortable, understanding that this is what we’re doing.

Is this person asking lots of questions? Is this person trying to connect with other people in the company? Is this person coming up with ideas? Is this person energetic? What happens when I give critical feedback or when I critique this person? Is this person coachable? Is this person fun to be around? Do I like this person? Like you just judge on these basic things. Does this person seem to be learning, like when I tell them something about our product, does this person seem smart and seem to be learning fast? Or is this person learning really, really slowly? So I’ll touch on all these things in the first week. And then the—The first week, you just want them to be showing up, learning the ABCs, meeting the people, getting comfortable, understanding that this is what we’re doing.

Second week, you really want to just see them how do they perform the job, let’s say you have them do research for leads, right? Even if they don’t directly with customers, you have a job for them so you judge them on the job. And if they have to generate leads, then you judge them on how many leads and what quality of leads are they generating on day 1, and when I give them feedback, how did they improve on day 2 and how did they improve on day 3. Just basically you judge them on their trajectory, like are they improving? Are they learning? Are they coachable? And then all the other things. Does this person seem to be bothered when they’re rejected? Does this person seem to be inconsistent? So, some days, they’re really excited. Some days, they’re really depressed. High energy, low energy. Showing up really early, showing up really late. Forgetting things. Not having thought about things, mess something up. Does this person—like just judge them on all these little details. And, it’s basically a confidence meter. So, what you want to do is at the end of the four weeks, let’s say, you want to arrive at 100% confidence or 90% confidence that this person can be a superstar in this job. You start at 10%, right? And all you’re trying to do is while you’re spending

Just basically you judge them on their trajectory, like are they improving? Are they learning? Are they coachable? And then all the other things. Does this person seem to be bothered when they’re rejected? Does this person seem to be inconsistent? So, some days, they’re really excited. Some days, they’re really depressed. High energy, low energy. Showing up really early, showing up really late. Forgetting things. Not having thought about things, mess something up. Does this person—like just judge them on all these little details. And, it’s basically a confidence meter. So, what you want to do is at the end of the four weeks, let’s say, you want to arrive at 100% confidence or 90% confidence that this person can be a superstar in this job. You start at 10%, right? And all you’re trying to do is while you’re spending

So, what you want to do is at the end of the four weeks, let’s say, you want to arrive at 100% confidence or 90% confidence that this person can be a superstar in this job. You start at 10%, right? And all you’re trying to do is while you’re spending day in, day out with them, you want to see is this scale moving up? Are you going from 10% confidence they can be a superstar to 90%? Or is this scale not moving? Or is it going into the minus section? Or is it just staying at 10%. Like even if it’s improving, if it’s not improving fast, I’m worried. But if it’s not improving at all, that is your—the answer to your question.

When do I know that I need to fire somebody?

Lots of people ask me the question, “Steli, when do I know that I need to fire somebody?” And my answer is when you are thinking about it, like the first time you ask yourself this very question is the moment to get rid of this person. The moment you go, “I don’t know if I should let this person go,” that’s the moment to let this person go. It’s the beginning of the end. So, you just try to gain more or less confidence if this person is really going to be amazing at this job.

Which is more important: sales expertise or industry expertise?

All right. Next question. “Which is better if selling our product requires a lot of industry knowledge—to hire somebody who knows the industry super well but is not good at sales or somebody that has zero product knowledge, industry knowledge but is really good at sales?” If you put a gun to my head, I would always hire sales expertise over industry expertise because industry expertise is much easier to learn than, of course, sales expertise. And if somebody sucks at selling, no matter how much they know about the industry, they’re not going to be good at it, good at selling in that industry typically. There are exceptions to this

There are exceptions to this rule though. So let’s say you’re selling to, you know, science professors. You have a very technologically difficult product. It might be that somebody that’s not that great at—well, I don’t even know. Like, no, I’m not sure, man. I mean even the industry is like—even in like the medical space where people sell to doctors very, very technical products, these people are not doctors oftentimes. These people are much better at selling than they are being scientists or medical doctors. So, I would always value sales experience over—or sales skills over industry know-how, I think, in general. No problem. All right. Next question, training. “We make—” This is going to be the last two questions, Matteo and Nick, and then we’re going to have to call it a day. And if you have more questions, I want to hear all your questions. I want to answer them all. Shoot me an email, [email protected] I’ll answer them in private in

No problem. All right. Next question, training. “We make—” This is going to be the last two questions, Matteo and Nick, and then we’re going to have to call it a day. And if you have more questions, I want to hear all your questions. I want to answer them all. Shoot me an email, [email protected] I’ll answer them in private in email later on. So, last two questions for today’s webinar regarding training. “We make trainings out of webinars. We have an audiobook library, record calls and feedback them.” Awesome. Perfect. Yeah, that’s all really good best practices.

Do you like Oren Klaff’s Pitch Mastery stuff for B2B security selling?

Nick asked, “Do you like Oren Klaff Pitch Mastery stuff for B2B security selling?” Yeah. That’s the guy—Oren Klaff is the—is that the guy with the book that’s like Pitch Anything or something? If that’s the guy—yes. I think that book is good. I think the framework is fine. I don’t—listen, I’ve read a million sales books. I don’t subscribe to any philosophy as being “the” philosophy.

There are some things I agree and disagree with with him in specific. I don’t know his pitch mastery stuff. I don’t know if that’s anything different from his book. But I think there are some good things in there, but I don’t think everything there will work and I don’t think everything works for all personalities. He’s a very certain type of personality type. So, yeah, I think he has some good stuff, but I don’t subscribe to any sales philosophy or methodology as like gospel, as like “Yes, that is the framework. That is the only truth or the truth.” You have to pick a truth with most of the stuff and go “Oh, this makes sense. This works. This I want to try.” But you have to be experimental. “I’ll try it. I’ll see what the results are. I’ll adjust, pivot, update and move along.”

How to get in contact with Steli

All right, guys. That’s it from me. Greetings to Prague, Austria, Germany, the U.S., everywhere else around the world where you are at. I don’t think we have like tons of people that subscribe to this webinar that got the recording. You all guys and gals are going to get the recording if you want to re-watch any part of it. And as always, just shoot me an email, [email protected] if you want to get more info. I haven’t done a webinar in a while, so this was fun. Thanks for all the amazing questions. Let’s go out there and crush it. All right. Goodbye everybody. Bye-bye. [End of transcript]

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