Hack & Hustle

Essential Sales Skills For CEOs Webinar

If you're a CEO or founder and want to get a quick introduction to essential sales skills for your startup, this webinar is a good place to start. 34 minutes (or 17 minutes if you watch at double speed) and you'll know the most important fundamentals of sales that truly matter.



Welcome to Essential Sales Skills for CEOs. I'm super excited about this group today, amazing founders and CEOs in the session. We're going to go through the webinar and talk about all the ways that you need to think about sales and the basic sales skills that you have to have if you're a CEO and a founder and somebody who's running a business. And then also how you need to think about all the people in your day-to-day job that you're selling to, and what you're selling them in the first place. So we're going to really go deep in sales focused on the CEO level.

First, let me share a little bit of background. So I've been a founder and CEO my entire life since I dropped out of high school when I was 17, 18. So I'm completely, you know, unqualified for any kind of job. I'm totally unemployable, but I've had at least the title of CEO for a very long time. And I've been selling to CEOs for a very long time.


The latest business that's probably most relevant to you guys is a company that we started called “Elastic Sales”. With Elastic Sales we helped over 200 venture backed startups in Silicon Valley scale their sales efforts. So we coach CEOs and founders in sales. We help them develop a sales process. We help to go out and sell to other businesses mainly in the B2B space. And the majority of those sales were actually to core decision makers, so CXO levels, many, many times to the CEO level. And we, as Elastic Sales, we always sold to the CEO, the final decision maker in basically utilizing Elastic Sales sales force to outsource sales and to get sales consulting and to scale their sales efforts.


We've worked with many, many companies in developing their sales process and scaling that. And in the process, we built a tool. At first we called it our internal “secret sauce” called “Close.io” that our sales people and our sales teams used in order to scale all these sales campaigns and outcompete their competitors. And you know, after a year of holding that piece of software close to our chest and calling it our “secret sauce” and our “secret unfair competitive advantage,” finally we gave in to all the demands from the outside market. We released Close.io, and it's been a tremendous success. Thousands and thousands of companies and sales people, people around the world, are closing more deals and making more sales using our piece of software.

So sales is really near and dear to our heart. It's in our DNA. It's the core thing that drives us and drives our business. And we're talking to CEOs and founders every single week, helping them with their sales strategies, helping them scale their sales forces and overcome their sales challenges.


All right, let's get right to it. So let's start off with Pitchology 101, right, the basics of pitching, the basics of sales. First of all, you need to understand that sales is nothing else than results-driven communication.

It's all about communicating with other people. It doesn't matter if it's in the context of a corporation or an individual buyer. You're always communicating with other human beings. And the goal of the communication is to help them make a decision, to drive a transaction, to drive a result, you know, yes or no. But you are in the results driven communication business.

And when you're managing teams as well as when you're selling yourself, you need to understand and separate communication for communication's sake versus communication for result's sake, right? So when you're in sales mode, and as CEO, you should always be in sales mode. It doesn't matter if you talk to your team to build something, if you talk to the press, if you talk to, you know, co-founders, employees, investors, you're always in sales mode, and talking is not selling. You know, you really need to focus on speaking in a way and communicating in a way that's actually going to drive a result and that has a result at the end of it as the end goal and the core driver of it versus just communicating for the sake of hearing yourself speak. Right?

And that's where sales is the closest to sports, in a way, and why a lot of people that are great at sales are actually people that are very competitive and might have had a background and history in sports because in sales you have a scoreboard. It's not just like, “Oh, I communicated great today, and I think I made some really amazing points.” Nobody gives a shit. Like, “I played really well today, but I didn't score anything.” Nobody gives a shit, right? The only thing that matters is how much, how many results did you drive, how many, you know, scores did you make if you were on the court, if you played basketball, whatever the competitive sport is; and in sales how many deals did you close? Nothing else matters.

And the other thing about that is it doesn't matter what the results were that you drove yesterday. You could be the best of the best, the best of all time. You could have been like Michael Jordan at his prime. When he went on the court for a new game, the score as zero, zero. Nobody said, “Well, this is Michael Jordan. He starts off with, you know, 30 points ahead because he's already worked his ass off for the last couple of years and he's the best of all time.” Nobody gives a shit.

The score he starts is zero. It doesn't matter what your results were last week. You have to perform again. You have to constantly drive results. And that's what it's all about. And as a CEO, you should only communicate to actually drive a result. No other communication should be part of your day-to-day life and the day-to-day where you do things and communicate things.


Because sales is a result driven activity, you know, you're never going to always just get wins. Not every throw is actually going to score. So you're more likely going to get more noes than yeses. You're going to have more failures than successes. If you opted to actually drive a result and get to a yes or no transaction one way or another, you're going to have to live with pain and rejection and failure. So you got to get used to that. And in sales, it's all about figuring out and training your own tolerance for pain and training your own tolerance for rejection. Right?

Most people design their lives around rejection. They design their lives around creating safe spaces where they're going to have to face as little rejection as humanly possible. When you're a CEO and you're selling, you need to get over yourself, which a lot of CEOs – a lot of CEOs have this problem that because they have this “title” for whatever the fuck that's worth, because they have that title, that title is seen as something that's prestigious, they only want to go out and sell when they know they're going to succeed. They don't want to fail in front of their team and staff. They don't want to look stupid. So they always kind of pick and choose what deals and what interaction they should get involved with only when they feel really, really, really confident that they can step in as the CEO and fucking drive the win and make this a big success and close the deal or whatever it is.

You have to get over yourself. You know, if you're only winning as CEO when you're interacting in sales conversations, you're not selling enough. If you're only winning, you're not taking enough risk. You need to fail. You need to show your entire team, organization, the public that it's okay to fail. It's okay to lose when you're playing to win. It's fine. As long as the scoreboard all in all has you ahead, you're fine. It doesn't matter how many times you took a swing, or throw and didn't hit the basket. So it's all about actually figuring out a way to tolerate and manage your emotional household and be okay with rejection. If you're not getting noes, if you're not getting rejected as CEO, you're not selling enough, you're not taking enough risk in sales. You need to be out there and figure out a way to manage your own emotional household and manage the way that rejection will be part of your daily life, hopefully.


Right now a lot of people and a lot of especially inexperienced CEOs – there are two camps: inexperienced CEOs when it comes to sales, people that maybe are very technical or don't have like a long background in sales; and also the other camp, people that love themselves talking, like super outgoing, super gregarious kind of personalities that think talking equates to selling – these two groups of CEOs think that selling is all about hearing yourself speak, selling is all about talking, selling is all about stealing the show and walking to a room and like babbling on forever and, you know, whoever has the most percentage of talk time in a conversation won. Nothing could be further from the truth, right?

In sales, the person who asks leads the conversation. Not in sales, in life, the person who asks the questions is leading the conversation, is focusing and directing and shepherding the conversation IN the direction you want to. You can only sell if you have understanding. You can only have understanding if you ask questions and you actively listen. Sales is all about first qualifying the prospect, qualifying the opportunity before you actually go out there to sell.


Don't throw darts in the dark. Too many people do that. You come into a conversation, you think, “Oh, this could be a potential buyer for a product so let me go on and tell that person everything there is to know about our business, and I'm going to throw as many darts in the dark,” darts representing value propositions, features, functionalities, fun facts. “I'm going to keep on saying, 'Well, our product is this and it does that and we have this and we have that.' I'm going to just throw as many things as possible, and something will surely hit.” Right? That's kind of the most unelegant, brute force, stupid way of selling. And what's going to happen as a results is the person will stop listening to you because you're like this overbearing person that is so self-involved and only in it for yourself. And it's impossible to listen to somebody and actually remember the 25th value proposition of that product. nobody is capable of doing that. And we've all been in these kind of very counterproductive conversations.

You can't just come into a conversation and sell. You come into a conversation to first get to learn and get to understand who it is that you're conversing with, who it is you're communicating with.

  • What are their needs?
  • What are they use cases?
  • What are their goals and challenges and obstacles?
  • Who is this person that I'm selling to and what do they need?

And once you actually get to understanding, not just surface level understanding but deep, real understanding of somebody's situation, then and only then do you have the permission to sell. And then and only then do you have the ammunition to sell because you have real targets.

You know, oh, this person really, really cares about X, Y, Z and I know why they care about it and I know the context, the environment in which they care about this. I really have a deep understanding so when I now start speaking to pitch them on our product, both do I have the authenticity that I believe our product really solves their problem; but I also a have clarity of what I should focus on. Instead of telling them everything our product can do, I'm going to tell them what our product can do that's going to help them and that I know is a priority for them.

So you always want to qualify first before you actually start selling anything. You always want to ask questions before you start assuming you know who they are, what they need and start pitching them on those.

And when you ask questions, make sure that you don't just ask them so it gives you a permission to pitch. Ask them to really understand them. Ask them with the real curiosity and an open mind and actively listen to what they say, the content of their words as well as the context, how they say it. Are they congruent? what's the environment like in which they are interacting and saying these things? Pay attention to not just what they say but how they say it and really drive understanding and qualify them. Yes, they are actually a really good fit for what we do and I understand what they need and why they need it, and I'm going to go and pitch them really effectively, throw in one dart into the target and hitting on the first attempt.


So the other thing that you need to know is that trust comes before any transaction, trust before transaction. Nobody buys anything if they don't believe everything you say, right?

So here's an example. If your phone rings after this webinar, and you pick it up and it's an unknown number, and the other person on the other line goes, “Hey, John. This is Steve. I'm calling from company X, Y and Z. I want to tell you you've won $1 million. Isn't this exciting?”

Are you going to get excited? Are you going to jump up and down from your desk, high-fiving your employees thinking you've just won $1 million? No! Chances are you're going to think about hanging up. You're going to say, “No, no. Not interested,” and you're going to hang up. Why?

Isn't the content of the call amazing? Isn't hearing and learning that you just won $1 million incredible value? Well, the problem is that you have zero trust. The problem is that you believe nothing that was just said. And the more amazing it is, the less you trust it.

It's not only about what you say, it's how you say it and who says it. Credibility and trust before any kind of transaction. You need to establish some level of trust before people can actually buy from you.

You need to understand that trust is being developed on three core levels:

  1. on the company level,
  2. the product level,
  3. and the personal level.

And if you can only establish trust at one level, do it on the personal level because that's the most vivid, active relationship, is you and the person you're selling versus – your product doesn't have a relationship with the person you're selling. Your company, which is this conceptual construct of multiple people and things. A company won't have a relationship. It always comes down to people.

So first, people have to trust you. Then you need to build some trust in your product, whether you're actually going to deliver what you promised.

And you also want to create some trust around your company, right? So why is this company going to be around? Why is this company known for keeping their promises, or fixing their issues. or keeping their words? Why should I believe this company is going to be around for a while? So interacting and getting into a relationship with them is not a waste of time that's going to be worthless in a few months because they're going to be out of business. So you need to build trust and tell people why they should trust your company.

You need to build trust around your product. Why will your product deliver? Why should people trust your product?

And most importantly you need to create trust around you as a person. Why should I want to be business with you? Why should I believe anything you say?


And you can do that explicitly and implicitly. And implicit is always better. Like you can always tell them about things that will make them think, “Oh, this person is trustworthy,” versus saying outright the words, “You should trust me.” Right? I'm always distrustful. The first thing I think when somebody is like, “You should really trust me,” is, “Oh, my God. I will never trust this person.” That's the most obvious thing to think.

So you want to be able to say things like, “Hey, here are the five amazing companies that have bought our product and here's the value they're getting and here's what they're saying about us. Hey, here's my background, here's my personal story, here's the companies that I've built, that I've led as a CEO and the results these companies drove and the legacy I've led them to become. Here's my background and story. Here's where I'm coming from. Here's where I am today. Here's where I'm going next.”

And you want to speak in a way that is authentic so people feel the congruency of your words so every word actually hits and people start believing you and trusting you. And a big benefit that you have as a CEO of a company is that the title alone comes with a lot of trust, right? The title CEO alone comes with a massive bag of goodies, and one of them is trust. People immediately assume you're important. People immediately assume they can trust you a lot more than your sales people or anybody else in your organization. So if you come into that relationship with all these like, you're already coming into this relationship with a lot more trust than normally people would have. And you want to make sure you're taking advantage of that.


Here's a big one about sales. You always – no matter what you do, product, service, I don't care what it is that you're selling – you always sell value. Nobody cares about your features. Nobody cares about how you've built what you've built, the functionality, the features, the buttons, the things. Nobody cares about the things that you're involved with all day long.

All people care about is what is in it for me. What have you done for me lately? What is this going to do for me, for my life?  How is this solving my problems? How is this making my life better? How is this making me more money or saving me money? Like why should I care?

And you have to focus on talking about value versus features. You have to talk about benefits versus functionality. And we all, we all forget this. It doesn't matter how amazing you are as a CEO. It doesn't matter how professional you are as a salesperson. Sooner or later you'll get so self-involved with your product, you're so focused on the features and functionalities and the bolts and bits and little pieces of how everything works that you're going to start talking about these things a lot more than you should be translating these things into value.

It doesn't matter that you're product has X, Y, and Z functionalities. The question is what kind of value does that drive to the other person and why should they care? Is this going to make them more money or save them time? Is this going to make them look good in front of their boss? Or, is this going to save them embarrassment? What is the core value that you could deliver with your product? Only talk about that.

Talk about the value you create. And then later one, as a follow up, you can talk about the vehicle that delivers that value, which in technical products, might be the features and functionalities of your product and the technical background. But the features and functionalities are always the deliverers of value. What people really care first and foremost about is what's in it for me? What is going to be the value of what you're trying to sell me for my life, right? Always sell value. Always do value-based sales. Never do features, functionality-based sales.


The next basic thing you need to know, understand, and master if you're a CEO in sales is the art of managing objections. There is no such thing as no objection sales. If you can pitch somebody, and they just say, “Yes,” and they buy – the most scary prospects for me are the ones that buy without objections. The most scary people that I try to hire for my company are the ones that want to start immediately without having any critical questions. The most scary potential investors are the ones that are immediately talk about investing without having any challenging objections.

Objections mean somebody is real. Objections mean somebody is trying to qualify ifhis is a good fit. Objections mean somebody operates in the real world with real constraints. I like these people. These people actually are the reason I exist. If people just bought left and right and had no objections, challenges and critical questions to ask, there would be no need to do sales anyway. Everybody would just buy. You wouldn't have to sell anything ever.

So objections are a good thing. You shouldn't hide or run from them or be annoyed or inconvenienced by them. You need to learn to manage them, anticipate and then manage. Hard preparation, easy fight.


So here's what you need to do. You should never compute an answer to an objection on the fly and in real time. What that means is if you're selling it doesn't to employees, to investors, to the press, to customers, you're going to get similar questions more often than not. 80% of the time, people want to have very similar objections and questions. There's going to be the, “We don't have any time. This is too expensive, what about security risks?”

Like there's going to be a set of questions, five, ten, 15, 20 questions that you hear again and again and again and again and again. And what surprises me is that people are surprised of hearing these things again and again and again. You know what? The more they hear them, the more annoyed they are that they have to deal with them. How stupid is that?

How about preparing for them and being excited when somebody has that objection because you're prepared to answer it effectively,and you know how to actually answer it in a way that drives your agenda forward and helps them, and helps you move the deal forward.

So what you need to do is once you know what the top five, ten, 15 objections are that you get all the time, sit down, you write these in a piece of paper or a document and you think about an answer that's effective, that only needs one or two sentences, no paragraph, no pages. You want to answer any objection as concise and precise as possible, one or two sentences.

You know what the secret is? It's not even that much about like how amazing is the answer. It's even more about – it's not so much how you answer it, or what you say when answer,but how you're answering it. Whenever you're able to

  • answer an objection in one or two sentences, and
  • keep eye contact, and
  • keep your level of energy and focus and clarity,
what it does is it doesn't just communicate the content of what you're saying, it also – the underlying message to the other party is, “Wow, this guy seems to not be rattled at all by this objection. This person seems to know exactly how to deal with it. This person seems to have a very high a level of clarity on how to manage that objection.”

The underlying message?

You're an expert. You know what you're doing, you've done it before.

That makes people comfortable, and comfort is - more than anything else - what people are looking for when they're bringing up objections. They don't just want to hear you answer and believe it. They want to feel like you are a pro, you've dealt with this before, they're in good hands.

So hard preparation, easy fight, you learn how to embrace objections, manage them, and use them as a tool to sell more effectively.


All right. Now the last of the sales basics for CEOs is the most surprising one. Duh, you have to ask for the close. Every conversation, every communication with somebody, needs to end with an ask for a close. Wow, Steli, you know, this is amazing. I'm so glad I enjoyed this webinar. I've never heard of this before. This is such a groundbreaking concept. Right? This sounds like the most stupid, obvious thing to say, but how is it that every single day I hear sales calls, I participate in sales conversations, where the end is the weakest part of the conversation and the CEO is not going for it? Again, looping that back to the fear of rejection, because they're afraid of hearing a no instead of embracing it.

Ask for the close:

  • Hey, are we in business yet?
  • Hey, what will it take for you and us to get into business?
  • Hey, what would it take for you, now that we've figured out that this is a good fit for you, now that it seems like we're really aligned and I was able to answer all your critical questions to your satisfaction hopefully, I'm curious, what stands in the way of us getting into business?
  • What needs to happen for you to become a customer of our solution?
  • What needs to happen for you to decide to join our team?

Like whatever it is, go for the close. And you know what? More often than not, you're going to get a no, or not yet. That's awesome. Embrace it. Anticipate it. It's a good thing.

What's the most powerful thing you can do when somebody tells you no?

Don't be rattled by it. Keep your smile. Keep your energy and composure. Show the other person that that doesn't affect you, that you anticipated that, and that it's fine for them to not quite be there yet now, but you're going to help them get there. Right?

That's when you come into the conversation, the sales conversation, from a point of friendly strength. Right? You're very friendly to them, but you're also, there's an underlying strength, like a parent interacting with a child that's really upset about something, or throws a tantrum, is coming from a place of knowing, showing the other party, “You know what? I've dealt with this situation before. I know you're not quite there yet. And that's okay. I'm going to help you and guide you through the process until you feel comfortable to make a buying decision.”

Nothing is more powerful than being okay with somebody saying no, and still keeping the conversation moving forward and focusing on servicing them into giving them everything they need to buy your product.

But you have to ask for the close to get the no. You have to ask for the close to get a close. You have to ask for the close to get to a result, a yes or no. You have to make a throw to make a point. You have to take a chance.

Too many times at the end of a conversation, a CEO or a salesperson will not actually really go for it. They will go, “Well, this was a great conversation. I'm really happy about it. Well, let's stay in touch and see how this is going to develop. And then let us know if you have any more questions, and we would love for you guys to buy our product. All right, bye.” Boom. What kind of a shitty close is this?

How about, “Hey, how was this call? Are you happy with all the answers? Are you ready to get in business with us?” Right? “Are you ready to go? Are you ready to rock and roll?”

Ask people for the close to get to a result. Yes or no doesn't matter. A no could be a not yet.

Even if it's a definite no, and there's a real good reason for why they'll never buy your product, you better want to know about it right now than wait for it for weeks. “Oh, are they going to buy or not? I don't know. We're still looking into the account every day and hoping they're going to upgrade or purchase themselves.” That's weak sauce, right? You have to go for it and ask for the close every single time.

The close might be, “Buy our product.” The close might be, “Let's schedule that next meeting.” The close might be, “Introduce me to somebody important.” But you have to ask for it. You can't get what you want if you don't ask for it. Right?


All right. So let's go to the next one. Fortune is in the follow up, and that's really the last step of the Pitchology 101, the Hustling 101, Sales 101 for CEOs, is you know, you know you have to deal with rejection. You have to go out there and pitch people and communicate in a result driven way. You have to qualify them and ask lots of questions to have a real understanding. You have to actually sell in a value focused way. You have to manage objections, and then you have to go for the close. And you know, more often than not, the transaction will not end until you have to do a little bit of follow up. And follow up is really where the fortune is. Follow up is where winning actually happens because nine out of ten times, everybody else will not follow up when a deal falls through.

So here's what happens. You have a sales conversation, you have a meeting, you have a recruiting call, you have an investor meeting or whatever it is, and it goes really well. And then they say, “Hey, let's schedule another call to talk some more,” and then send them an email to schedule the call and crickets, silence. You don't hear from them back.

So you send another email. You don't hear from them back. You wait a little longer, you send another email. You don't hear back. You call, you leave a voice mail. You don't hear back.

At that point, you start assuming, “I've been rejected. They hate me. They probably think I'm horrible and stupid. Oh, my God, I'm going to feel really shitty about this. I don't want to be meeting and keep getting rejected by their silence. So I'm just going to stop and call this a 'loss.'” It's the stupidest idea and the stupidest strategy you could ever apply.

When you have been in a positive interaction with somebody and they fall off the track and they don't communicate with you, you know how many times you should follow up?

Indefinitely! Forever.

You should never stop following up until you get to a result. Again, looping back, result driven communication. Silence is not a result. A no is a result. A yes is a result. But silence isn't.

So here's my simple philosophy. I always follow up indefinitely. I keep following up forever until I hear back. When somebody tells me, “Hey, fuck off dude. I really don't want to hear anything about this anymore,” I'll stop. I totally will stop. But until I hear back, I will never ever stop following up.

You know how many deals we closed, how many investors we got, how many things we've moved forward just by being the only ones that kept following up? A lot more times than you could ever imagine.

I'll give you a quick example, a story that I tell oftentimes. An investor, somebody that's so famous, all of you have used his product, the product that he developed and made billions with I can say with certitude, we got a warm introduction to that investor. Once we were fund raising, that guy replies and says, “Yes, I'm interested. I want to meet up with you guys.” We get all excited, high-five each other. We send an email with some times and dates to meet. Silence. We send another email, silence. We send another email, silence.

You know how many follow ups it took to hear back from him? 48 fucking follow ups, 48 follow ups, where he was totally silent. You know what, when we follow up, we weren't needy about it. I was referring back to the original emails. “Hey, you said 'yes'. What's up? I've followed up with you 12 times. That's not cool. Really, it would be – I really appreciate it if you” – like no!

Every single email, I was clear and to the point, short, precise and concise:

“Hey, another beautiful day in paradise. Here's a little tidbit of good news about our company. How about a quick call on Tuesday or Thursday at this or this time?”

I send another follow up:

“Hey, how about we should try to meet on Wednesday or Saturday.” Nothing.

Another follow up: “Hey, you know, here's another cool news. We just hit this milestone. Would it be possible to meet this week, either this time or that time?”

I just kept following up, professional, clear cut, one or two sentences, precise. After 48 follow ups, the guy replies and says, “Oh, my God. I'm so glad you kept following up. I'm so sorry. I suck. We had this big crisis. I had to fly around the world. I had to do this and that. Yes, can you come tomorrow to my office at 11 a.m.” We went there. We closed the deal. We got the investment.

That's how you win. Follow up when nobody else is following up, because everybody feels rejected and needy and doesn't want to be inconveniencing somebody. This is business. When you're in a relationship with somebody and you interacted with them and they give you positive feedback and said, “Yes, let's move forward,” they've given you permission to follow up. And it's not just rude to follow up. It's rude to be silent. Don't assume people are rejecting you. Assume people are busy. People have other things to do than to answer you. Something came up so keep follow up until you hear from them.

If you only do one follow thing as a CEO is instilling a culture of follow up in your organization, and you have to go first. Lead by example. Show your employees, your team, your investors that you always follow up and follow through to get shit done. Right?


All right. A last little tidbit on the sales side, pulling the CEO card. Like being – just by having the title of CEO, deals will happen faster and better because people assume a lot of stuff with, “Oh, the CEO has stepped in to talk to us.” Right? You could give a junior salesperson the CEO title, and that person will probably close more deals next week just because they come into a conversation with like, “Oh, this is the CEO of our company.”

People assume importance, people assume authority, people assume intelligence, all kinds of amazing shit with the title CEO. So just by having that title, just by giving yourself the title of CEO of your two-person company, right, I'm the chairman and CEO, just by that, people will take you more seriously, people will listen to you more carefully, and people will resonate and respond to your message a lot more powerfully.

So you have to help your team. If you have a sales team already or team that sells, that goes out there, you have to get down and dirty. You have to step in and help your team close deals especially the important ones. Help step into your HR recruiting team to hire people. Step into, you know, the industry and fund raising side. You have to be in the front lines using your title, and using the authority and the magic and the unicorn sprinkling, all the cool goodies that come with that title to get shit done and make transactions happen. So support your team and utilize that title to make stuff happen.

And then one quick other tip is that one of the more core important things about the CEO title is that people assume that you are busy, that you are important. Being busy and important assumes that you don't have time to waste. So when you go into sales conversations, one easy hack to make the other person really feel implicitly that you're important is to have time constraints. If you go into sales calls as a CEO and you take two hours for like a $100 a month deal, you know what the other person will think? Even if they appreciate that you take all the time in the world for them, they will assume you're not important. They will assume you have nothing better to do than to take two hours to close a $19.99 monthly subscription deal with them, all right?

So here's a simple hack. As a CEO, everything you do should have a short and precise time line. You do 15-minute sales calls. You don't do one-hour sales calls. You come into the conversations with having real time constraints. “Hey, my name is Steli. I'm the CEO of Close.io. I'm super excited to talk to you today. I'm going to highlight to be respectful of your time that I'm going to have another call in about 15 minutes. My day-to-day is a little crazy. I apologize for that, but I think that if we both focus, we're going to be able to accomplish our objectives and get really a lot of things done. Why don't you start and tell me the three things that you want to focus on? And then we'll go ahead, and we'll try to make it happen.” Right?

Just by saying, “Hey, I have a real time constraint. I have another call in 15 minutes or 30 minutes, but I think that amount of time, if we focus, will help us get everything done,” just by that and having that kind of energy of like, “I need to get you done. I don't have time to babble on for or talk about the weather and everything. I'm here. I'm focused. I'm going to give you all my attention. Then I have to move on to something else,” just by doing that, you're going to have real impact, and you're going to implicitly communicate to the other party that you're important and busy.

And people love to buy from people that are busy and that are important. Right? It makes them feel comfortable. It makes them feel like this is somebody that's important for a reason. Probably they're very intelligent and successful. So doing business with them is probably going to be a good idea. Right? Use that. 

Read More

Inbound Or Outbound Sales - Which One Should You Focus On?

I share a lot of advice about outbound sales - thus many people naturally assume I'm an outbound advocate. I'm not. It's just one of the things I do, outbound is a part of the puzzle of success in business to me. But I don't think every startup should do outbound sales.

When it comes to inbound versus outbound, I'm not dogmatic - I'm pragmatic!

Fun fact: Close.io is doing zero outbound sales. All our growth is 100% inbound generated! There will come a time when we get outbound sales going, but right now we're too focused optimizing and scaling the inbound part of the business.

Cons of Outbound Sales

Outbound sales has taken a lot of flak - for several reasons...

Public Enemy Number One


Nobody wants to be cold called, even sales reps who cold call don't want to be cold called. I'm more receptive than most to cold calls because I'm a sales aficionado, I appreciate good salesmanship - but even I don't look forward to being pitched.



When you're doing outbound sales, you're interrupting people. Everybody is an expert nowadays on filtering out interruptions. The average US citizen is bombarded with more than 2000 marketing and sales messages every single day (number varies depending on methods used to measure, but 2000 is actually the low end). It's like our brains have a subconscious TiVo or adware program running in our brain that immediately blocks anything that triggers the sales pitch alarm. You basically have to buy, beg or bug your way in.

High-pressure Sales Tactics


These are still commonly used and encouraged in outbound sales organizations - but you can (and should) be a smooth operator rather than a sales bully.

Time Inefficiency


Outbound sales reps waste a lot of time on mind-numbing tasks. They spend only a small part of their workday practicing their core skill: closing deals. (Which is something we're mitigating with our outbound sales software, but it's still a major pain point).



Outbound sales stops working as soon as you stop working. One of the big advantages of inbound sales is that it keeps generating leads even if you stop doing it. But as soon as you stop doing outbound, it stops generating new business.

Pros Of Outbound Sales

Now let's look at the flipside of the coin.

It Works


Yes, it's 2014. Yes, 'the buying cycle has changed', we're living in unprecedented times with social networks having changed the game of sales. But the fundamentals of salesmanship that worked in 1914 are still working now, and will still work 2114. Outbound sales brings home the bacon.

Predictable & Scalable


Once you have developed a sales process, you have a predictable, scalable growth mechanism for your business. Hire a new sales rep? You know how the actions you take now will affect your revenues three, six, nine months from now. Ask any business owner - that kind of simple formulaic predictability is a beautiful thing.

Power To Choose Your Customers


Outbound empowers you to pick your customers. Outbound is hunting - you pick a target and go for it. Inbound is fishing - you hang a fishing rod in the water and hope that a fish will bite, but your control over what kind of fish will bite is miniscule.

You Determine The Timing & Medium

Outbound sales gives you control to determine when you want to interact with prospects. This is the flipside of the "interruption" coin - rather than having to wait prospects to reach you through inbound requests when they are ready, you reach out to them when you are ready.

You also determine the medium of your interaction - be it an email, a phone call, meeting them at industry events or even knocking on their doors.

Immediate Results

Outbound sales can generate new business quickly, whereas inbound takes a long time to build up. If you want fast growth now, outbound is your friend.

Targeted Reach

If you're selling to professionals, outbound allows for much more targeted lead generation. This kind of laser focus allows you to execute with a higher level of precision and accuracy, and thus be much more effective. Want to reach the VP of marketing Citigroup? Good luck trying to get his attention with inbound tactics. 

Higher Level Of Engagement


The most impactful and influential sales outreach possible is a human one-on-one interaction. It allows you to truly engage with the buyer. Everything else pales in comparison when it comes to the impact you can have on an individual buyer.

Is Outbound Right For You?

It really depends on what the focus of your business is now, how fast you want to grow and what kind of business you want to run.

Your Strenghts

Whether or not you've got what I call the "hustle DNA" and are a natural born sales person - you should be doing some outbound sales, just for the lessons it'll teach you. But don't try to force yourself and break your back over making outbound successful if you have other means for growth.

Your Market

Are there other companies doing outbound successfully? If yes, how are they doing it? Study their outbound sales process and learn from the market.

Your Results

old cash register

Ultimately base your decision on the results you get. Outbound is probably the least trendy, hip, cool, awesome, amazing thing a startup can do to grow the business. But you're not in business to get admiration from your peers and the press, it's not a popularity contest.

Business is about the bottom line. The only thing that matters is: does outbound sales make your business more successful or not?

Read More

Finding Others To Fix Your Business?

When we were running ElasticSales (outsourced sales on demand for startups), we had this one certain kind of prospect that scared the living hell out of us just by wanted to work with us. These were the customers who wanted us to fix their business with the magic of sales, some of them willing to throw a lot of money at us to make it happen for them. Most of the time we were strong enough to say NO.

Often times these are the entrepreneurs who build a beautiful product and are in love with their idea - and think the only thing missing is some marketing / sales / biz dev guy to come in and "do the business stuff". They usually misunderstand what the business side of business is about, and have very little appreciation for it. 

Sales are either slow or non-existent. They're not generating enough revenue. They don't know how to make their business work... and want "others" to figure it out for them.

Here's an ugly truth that outsourced sales companies don't want you to know:

If you can't sell your own product, no one else will be able to sell it for you either.

And that's a bitter pill to swallow, especially if you are that entrepreneur struggling to keep your business alive. You'll become so desperate that you clutch at any straw you can find. You'll think: 'Hey, these guys know sales, I'll just bring them in and they'll do it for me.'

But that's just wishful thinking, born from the seed of desperation.

The truth is, if you have zero (or next to zero) sales, then...

It's not the sales part that's at fault. It's your product.

If you truly have a great product, you will be able to close at least some deals.

Even if you're not a sales person.

Even if you suck at sales.

Even if your pitch is flawed.

Even if your hustle is lame.

If your product is solid, you'll be able to close your uncle, or your ex-boss, or your buddies' dad, someone...

Figure it out before you source it out

It's ok to outsource sales because others are better at doing it. But first, you yourself need to have figured out the basic sales model. Don't just outsource something to somebody else that you don't understand yourself. 

Don't expect some professional sales team to bring you from 0 to 1.

That step from 0 to 1 is always the step you need to make.

Taking it from 1 to 5? From 5 to 12? From 12 to 23? From 23 to a 100? Yes, bring in outside experts. But 0 to 1? That's your job!

But what if you really do need help?

What if you really can't get from 0 to 1 by yourself? Well, it's ok if you are looking for help on how to figure it out. It's ok if you're willing to do what it takes, and need someone to coach you through the process. 

But don't look for someone who will figure it out for you. If you're looking for somebody who will do all the steps for you that are necessary to figure it out, you're fucked.

Figuring out the basics is your job. You don't need to figure it out until the very last detail - but at least you should have mastered the sales exploration phase and be ready to transition into the sales execution phase.

I wrote about the four stages of startup sales in my sales hiring post, and the transition point between sales exploration to sales execution is between stage #2 to stage #3. You want to have something that the outsourced sales company can build upon and optimize.

If you have nothing, that's not enough :)

Read More

How Can Sales Drive Customer Success?

Customer success is one of the most essential ingredients for sustainable growth in SaaS. Having a dedicated customer success manager (CSM) is great - but it's just as important that sales owns customer success too.

From a sales perspective, there are three main stages where customer success measures can be implemented:

  1. pre-sell: before they're a customer,
  2. post-sell: while they're a customer,
  3. post-cancellation: after they're a customer.


What can sales do before a deal is closed to improve customer success? How can sales drive customer success before a prospect converts into a paying customer?

Qualify For Fit

As a sales person, you want to close deals. It’s tempting to skimp over the qualifying part of the sales process. If a prospect shows interest, if you believe you can make the sale, clearly you should make the sale, right?

Not so fast my friend.

As a sales person, it’s your job to sell to those who should buy your product, not to those who want to buy it!

Properly qualify prospects, and then ask yourself: Is this prospect really a good fit?

Example: Qualifying Prospects

A prospect might come to us and say: “We need bulk email.”

The easy thing to respond? “Oh yeah, great, we have this powerful bulk email feature! It’s going to make you a lot of money and save you a lot of time!” And then you push that prospect into becoming a customer.

But do you really understand what the prospect needs?

Instead, follow up with more qualifying questions.

  • What kind of bulk email do you want to send? Marketing, newsletter or sales bulk emails?
  • What kind of tracking, which metrics do you need on those emails?
  • Do you need HTML style emails or do you need text only?
  • etc.

Asking these questions will help you determine whether that prospect is really a good fit or not.

If you sell to a prospect who isn’t really a good fit, just because they want “bulk email” and your product has “bulk email”… they’ll be in for a surprise if the bulk email function doesn’t match their use case.

And by that time they’ll have invested their time and money into your product - when you could easily have saved them both by asking some simple qualifying questions. The customer will cancel, and walk away from your company with a bad experience, and a bad taste in their mouth.

Qualify For Risks

What are potential risks if this prospect becomes a customer? Can they really afford to stay with you? Can this customer survive long enough to truly be a valuable customer? What could potentially affect this customers’ lifecycle?


At Close.io we had a new sales person who sold a deal to a new startup. Our sales rep and that startup had something in common: they both lacked experience!

Startup: “We have no sales people now, but we’re going to hire 30 interns, and have them cold call potential customers. So we’ll need 30 licenses for Close.io, and then by the end of the month we’ll sort out the interns who didn’t make the cut, so we'll probably keep 15 to 20 licenses.” They had previously shared with us that they had received about $30,000 or $40,000 in funding.

Inside the mind of our sales rep: ‘Wow, 15 to 20 licenses, that could be $3000 in MRR!’

He eagerly pushed to close the deal. “Look, here’s how we’ll do it. You put in your credit card now, and we’ll book you for 30 seats, but we won’t charge for you 30 days. After that, we’ll start billing your card for the remaining 15 to 20 seats.”

What happened next?

Before the trial even expired, 29 of the 30 licenses cancelled! One month we booked $3000 in MRR, the next month we had to put in $2900 churn. Deals like that can totally screw up your numbers.

This sales person should have qualified the risks! They should never have closed this deal. They could just have said: “Hey, do the trial, and after the trial - when you have your numbers down, and really know how you’re going to use Close.io - then we’re going to take your credit card number and close the deal, based on the actual number of users.”

Our sales person should have realized that this was a high-churn-risk customer:

  • With $30,000 or $40,000 in funding, they’d burn through their cash real quick, especially when they hire 30 interns!
  • Hiring 30 interns to do cold calling - without experienced sales leadership! - and expecting them to bring in deals isn’t going to work in the real world. They just didn't understand professional sales.

Two huge red flags. This is an extreme example, but it’s very common for sales people to not properly qualify for risks, and it'll affect customer success later on.

Set The Right Expectations

Most sales reps sell benefits and make promises to prospects. But you want to take it a step further than that: set the right expectations for what being a customer of yours really entails.

Example: Ease of Use

Prospect: “I want this product to do X, Y and Z easily.”

Sales rep: “Oh, great, this is super easy with our product, you are going to do great!”

When in reality, it might not be that easy - especially if your prospect isn’t tech-savvy, or doesn’t have the kind of expertise and experience you possess.

Understand where they are coming from:

  • Have they used a product in your category before?
  • Do they really understand the workflow they need?
  • Did you explain to them what the actual workflow is going to be?

Example: Promising Benefits

Be mindful of how you convey your benefits.
Don’t say: “You’re going to see a 15% to 30% increase in productivity.”
Do say: “Our customers see a 15% to 30% increase in productivity on average.”

If you promise them 15% to 30%, and after using your product they get 10% - they’ll be disappointed. You will have disappointed them. In the worst case they’ll churn - but even if they stay, you’ll have screwed up the relationship. They’ll always take your word with a grain of salt, will always assume you’re overpromising, and they’re less likely to refer you. The impact you’ll have on them will be diminished because of lack of trust, and that can affect customer success later on.


Do you already have an onboarding process in place for your customers?
If not, create an onboarding experience asap - preferably a good training on how to use your product.

Example: Close.io Onboarding

In the early days, we offered personalized 1-on-1 training sessions to all customers. As we grew and scaled, we started offering a weekly training webinar, where we cover different aspects of Close.io, and how to set it up and get going.

This training has been extremely popular, and it has been extremely effective at helping our customers become better at using the product, and getting more value out of it.

Why Do You Need Onboarding?

It’s not enough to sell the benefits of your product. You also want to sell them the actual implementation. Think about a diet product - you can say: “This diet system will help you to lose 30 pounds in 6 weeks!” They buy, and then you tell them: “Only eat carrots for 6 weeks, and go for a 5 mile run every morning.” Well, yeah, they would probably lose 30 pounds if they'd do that, but nobody is going to do it.

When customers start using your product, they are going to run into challenges. They are not going to fully understand how to use things optimally right from the start. It does require training. They need help configuring and setting things up optimally. If they aren’t using your product successfully - they will churn.

That’s why onboarding is so important.

Are You Selling The Onboarding Experience?

If you DO have onboarding, then SELL the onboarding experience to your users! Don’t just passively offer the onboarding. Instead, proactively sell them on participating: push, convince and coerce them to do the onboarding!

At Close.io, every time we close a deal we tell them: “We’re very excited to have you on board! Now that you see the promise in the product, we want to also make sure that we deliver on this promise. The best way we can deliver is by helping you come on board and train you on Close.io, because it can be very complex and has a lot of nuances. So I highly recommend this Thursday, you do our training webinar, here’s the link, please sign up and have the entire team sign up, and whenever you add new users, please have them sign up.”

We’re selling our customers on the onboarding! It’s not enough to take their money now - we want to keep them happy, successful and productive, so that they stay onboard.

Sell your onboarding, so that your customers actually DO the onboarding!

Get Long-Term Commitments

Get prospects to sign up for a long-term contract or annual plan. You want to get a long-term commitment from them so that all the work you invest into them pays off - and they get a better price and more value.

But you have to sell this. Many startups fail at this - they assume customers are going to sign up for annual contracts by themselves if they want to, and make no serious effort to convert them to annual plans. “We’ll just give them an amazing experience with out amazing product and our amazing service, and they’re going to automatically stay!”

That’s not good enough.

Push people to sign annual contracts. Even before you close the deal. And if somebody came on board on a monthly plan, pitch them again in the next month on the annual plan, and say: “Hey, you’ve been with us for a month. How has the experience been?”

And if they’re happy with it, ask them: “Great, do you plan on using our product for the next 6 to 8 months?” - “Yeah!” - “Well, why don’t you save money and do a one year contract with us, this way you’re going to be with us anyway, but you’re going to save ___ dollars”.

This is how you get more people to commit to annual plans, and reduce churn.

Later on when customers experience problems, they don’t just quit. They won’t be the fickle customer who just turns around and leaves when there’s an issue. And this is in their own interest as well, because switching from one vendor to the next is just going to slow them down, they'll have to change the way they work, and more often then not it's just an out of the frying pan into the fire situation.

They’ll be more committed to finding a solution, and sticking with your product - it buys you more time to solve their problems and make them happy again, and it allows you to invest more effort into making them successful.


Just because you’ve sold someone and they're now a paying customer doesn’t mean your job as sales person is finished. Beautiful sales opportunities wait among your current customers - don't miss out!

Check in with customers you’ve closed a month or two ago. You want to find out:

  • How are they doing?
  • Is your product serving them well?


Ask your customers:

  • Whats the plan for growth?
  • How many users are you going to add over the next few months?
  • What are other opportunities within this organization to sell this product? What about your support department? What about this other department?

Help your customers to put a plan together to bring more people on board.


Ask your customers if they can make referrals to other people in other companies who can also come on board.

Few sales people do this, but if you consistently ask your current customers for referrals, it can become a substantial source of high-converting sales leads.

Let’s say a customer refers you, and you successfully sell to that referral. You’ll have accomplished several things - in addition to closing another deal:

  1. You have increased the perceived value of your product in the eyes of the referring customer. Since the person they referred obviously saw enough value in it to make a purchasing decision, others obviously too see the value in this. Don’t underestimate how much social validation matters, even in a professional B2B context.
  2. The referring customer (rightfully) feels they made an impact, they feel empowered because they made a difference - thus, they’re more likely to make more referrals.
  3. Make the new (referred) customer thank the referring customer for making the referral - and they're going to be even more excited to keep on referring you.

Problems & Technical Issues

You’re going to run into problems, especially if you’re working in a tech company. You’re going to have downtimes, things break, bugs… and your customers are going to get pissed off.

So how do you solve these problems? You either do it from a position of weakness, or from a position of strength.

From a position of weakness:

  • Apologize to your customers.
  • Fix the problem.
  • Try to compensate customers.
  • Apologize and beg for their mercy some more. :-(

From a position of strength:

  • Apologize to your customers.
  • Fix the problem.
  • Try to compensate customers.
  • Turn lemons into lemonade. :-)

Example: Close.io's Calling Outage
Our VOIP provider suffered from a DDOS attack. The calling function of our sales communication platform was down for an entire day. Now this is a very rare event, and our VOIP provider had never experienced this before. It affected all our customers with calling plans - they couldn’t make any calls from within Close.io.

Some customers complained vehemently. They were upset and angry about a day of wasted productivity and lost opportunities.

We did what any good software company would do: work furiously on resolving the issue, and communicate very transparently what was going on, what users should expect, and finally when the problem was fixed.

We personally gave extra attention to every single customer.

A crisis like this is your chance to shine.

Some of our customers demanded compensation for the productivity loss.

What most companies would say: “Of course, here’s a refund!”

What we said (and what every company who strongly cares about customer success should say): “All right, we’d love to help you guys out and actually strengthen this relationship. You can see how we responded to this situation - and if you’re happy with the way we responded to it, here’s what we’re going to offer: we want to give you guys an additional 5 or 10% discount. But we want to make this a long-term relationship both ways, so that we can work on your success together. So we ask that you guys sign a 1 year contract.”

We had five or six customers who demanded compensation.

How many do you think signed up for a one year contract?


Always respond from a position of strength! Asking a customer for something in return is fair game. Contrary to what many people assume, it even benefits the customers, because it gives you more leverage to make them successful.

If you do it right, the relationship with these customers will improve - as was the case with the customers who took us up on we’re sorry offer. Just like in personal relationships, overcoming hard times together strengthens business relationships.


All is not lost once a customer cancels. These make for some of the most challenging, but also most worthwhile sales conversations you can have. Skilled sales professionals have an opportunity to turn these customers around and make them successful with your product. Hustle hard to keep them on board - but don't go comcast on them.

What do you do when a customer cancels their service with you?

First, you call them and ask them for feedback. You want to know what the issue is.

Second, you try to save the customer by communicating from a position of strength. Find opportunities to resolve the issue if you can. It’s worth to invest effort into this. 

At Close.io, every single customer that ever churns, we call and figure out exactly why they churn.

First thing is to understand: What is the reason why they churn. Understand what made them want to leave.

Example: Going Out Of Business

Customer: “Well, we’re cancelling because we’re going out of business.”

Sales rep: “I’m sorry to hear that. Tell me a little bit more about this situation.”

And try to offer customers some help.

If it means that they just need to cut some costs for some amount of time, and then hopefully try to get their business back on track, then you might be able to help financially. Not by giving them money, but by giving them an extended trial or a discount. Sometimes a bit of generosity can give them the leeway to get back on track. But if they’re going out of business for good, give them advice, give them help, give them the support they need - you know how much sweat, blood and tears it takes to build something up, and how painful it can be to have it fall apart. Little gestures can go a long way.

Example: Missing Feature X

Customer: “We’re leaving because your product doesn’t have feature X.”

Sales rep: “Ok, we didn’t have this feature. Did you know that our product lacks feature X when you first signed up? Did our sales do a bad job of understanding your needs? Did we do a bad job when it came to telling you whether or not we have all the features that fit your needs? Or is it something that you figured out later on, you just had a new need, and our product didn’t address this new need?”

The question here is: is that even part of your product roadmap?

Example: Close.io Missing Special Reporting Feature

Customer: “We’re leaving Close.io because we want reporting.”

Sales rep: “Ok, what type of reporting do you need?”

Customer: “We need reporting that graphs and charts how users are behaving based on X, Y and Z parameters.”

Sales rep: “Interesting. Now have you already found another tool that actually does that?”

Customer: “Yeah, we’re looking at this other tool that functions exactly this way.”

Sales rep: “All right, first let's step back and pause for a second. Why did you sign up with us to begin with? For what reason did you originally chose Close.io? What attracted you to us at first?”

Direct the conversation towards the benefits and the value of your product for the customer. This is simple sales psychology: it balances the equation a bit, and creates a counter-force to their desire to leave you. First understand why they chose you to begin with. Then understand what they specifically need, and where the mismatch is.

Sales rep: “All right, so you need this kind of reporting. How would that specifically work? What would that look like?”

Customer: “Well, X, Y and Z.”

Sales rep: “If we had exactly what you said, if we had it in this way, would you consider staying?”

Customer: “Yes, we would stay.”

Sales rep: “If we were able to deliver this feature in the next 2 to 3 months, would you consider sticking around for the next 2 to 3 months until you have that?” 

SCENARIO A [feature is on roadmap, customer negative]:
Customer: “No, it’s just not worth it for us to keep on paying you for two or three months until you release feature X.” 

Sales rep: “All right, how about this, we’re going to give you a 30% discount for the next 3 months, until we release the feature. And if you’ve used the new feature for a month and it does everything you want and need, we’ll put you back on your current billing and you can be a happy customer again. And if feature X doesn’t do everything you want and need, or you’re just not happy with it for whatever reason, no problem, you can still move out to another software system of a vendor of your choice.”

SCENARIO B [feature is on roadmap, customer positive]:
Customer: “Two or three months? Yes, we would consider staying!”
Get them to stay (use incentives if necessary). Frequently update your customer on the progress you’re making towards releasing feature X.

SCENARIO C [feature is not on roadmap]:
Customer: "Maybe."
Sales rep: ”We’re not planning on launching this feature, but here’s a workaround you might want to try, if it works for you great, if not then on problem.”
You still want to ask the question though to make sure that the lack of feature is actually is the root cause! Remember, it's ok to not implement features some customers request.
What’s the strategy behind this?

It’s about aligning the customers’ expectations with the value you provide, and it creates a shared goal for you and your customer within a defined time frame.

These kinds of arrangements turn churning customers into valuable long-term partners, allies and brand ambassadors.

Example: Customer Didn’t Get Enough Support

Sometimes customers churn because they haven’t received the support and customer care they needed, or an issue they were struggling with didn’t get resolved well enough.

This is a great opportunity for you to sell them on you again.

Offer them extra value and attention.

Own up to your problem.

Sales rep: “Hey, we’re really sorry that his happened. We’re committed to making this work. Here’s what we propose. Give us 2 weeks. During this time we’re going to give you an extra level of support, enterprise level of support - we’re going to give you support that we usually charge for. But you’re going to get it or free, we’re going to help you guys become successful, and deliver on the promise that we originally made you. Are you open to that, if we can do that, if we can fix that issue for you? If we can solve that problem for you, would you consider staying?”

Give them that level of support. Be rockstars. Overwhelm them with awesomeness. And then, at the end of those two weeks, make them sign a one year contract.

Sales rep: “Hey, were you happy with the support we gave you?”

Customer: “Yes, we’re happy, your team was awesome. Our problems are solved.”

Sales rep: “Great! Why dont we make this a long term relationship? You saw how we solve problems, you saw how we deal with issues, why don’t we get you guys on board for the long run? We’re going to save you some money, and we’re committing to you to deliver amazing customer success.”

That’s how you not only save customers, but come out stronger at the end of that process.


You now know how to implement sales-driven customer success in all three customer stages: before they sign up, while they are paying you, and once they want to leave. Keep a healthy balance - don't discount your product, or overdeliver on service, to the point where it becomes unsustainable for you. 

Read More

Sales Process Development: How Involved Should Founders & CEOs Be?

How much should founders and CEOs participate in developing an outbound sales process for their companies? Better to get their hands dirty and immerse themselves in the nitty gritty of sales, or to delegate it to someone else so they can make the big strategic decisions and work on other things?

This question was at the core of the challenges facing the man I recently had breakfast with: a highly accomplished CEO and founder of an incredibly successful SaaS company.

Their startup is doing great. Steady, sustainable growth through inbound marketing and channel partnerships. The whole machine is running beautifully.

Except that there's a lot more opportunity out there for them than what they're getting from inbound and channel partnerships. And our successful SaaS CEO is hungry for that opportunity. How can he get access to that vast untapped potential?

Say it with me kids: Outbound sales!

Developing A Sales Process

He did some things right: he hired a couple of young, ambitious sales reps who feel excited to tackle the challenge.

He learned about different sales tactics and outbound strategies. He did his best to supply them with the right leadership (he mentioned how he already replaced several non-performing heads of sales).

He spelled out what needed to be figured out:

  • lead generation
  • prospecting
  • qualifying leads
  • funneling high quality outbound leads to the account execs
  • what tools to use
  • using cold emails and cold calls to get to decision makers
  • etc.

But in all his efforts to get outbound sales rolling, there was one crucial thing that was missing:


He pretty much handed off the development of the outbound sales process to his employees, and spent about an hour a week to check in with them. That's not enough. 

In this crucial stage of your company, where you're experimenting and learning how to do outbound sales successfully, you as the founder or CEO need to be knee-deep in the sales hustle. You need to be actively involved, you need to participate.


You need to get your hands dirty doing all the things you want your sales team to do. Even low level activities like sourcing leads to reach out to, or dialing dozens of numbers in a row just to get one prospect to pick up the phone. Whatever it is. Do the grunt work. 

Why CEOs & Founders Should Be Involved In Building The First Sales Process

Many founders and CEOs push back when I tell them to do this. "But Steli, I could be closing six or seven figure channel partnership deals, and you want me to spend my time cold calling prospects that at best bring in a couple thousand in MRR?" 

That's exactly what I want you to do. Not because of the couple thousand in MRR that you might potentially get from doing cold calling. But because of the many millions of dollars your startup could steadily earn if you build a strong outbound sales process.

Bambi, Meet Gozilla

To build that sales process, you need to know what it's like to do all the things you want your sales team to do. You can't take some ideas you picked up from a book, from a friend who grew sales for his SaaS company by XX million dollars, or from the charismatic speaker at a conference.



You need to take your beautiful and precious ideas and see what happens to them when you put them out there in the battlefield of harsh realities. Because if you just hand your untested ideas over to someone else, and it doesn't work - you'll never know if it doesn't work because the idea was wrong, or because the person responsible didn't do it right.

"The best way to find product/market fit is to get in front of customers and validate your assertions. Start early, and validate before you build anything. Use wireframes of the product to walk customers through your vision, then keep validating throughout product development.

Develop objective listening skills, and don’t get caught up in selling too hard. Often entrepreneurs only hear what they want to hear, a trait sometimes referred to as “happy ears.” When a customer disagrees, you’ll often hear these entrepreneurs say: “They just don’t get it.” This is a good indication the entrepreneur isn’t listening."

- David Skok, Accelerate Your Startup: Get the Right Product/Market Fit

David writes about finding product/market fit - but the same principle applies to building your outbound sales process. 

Nobody Understands Your Business As Good As You Do

Nobody is as qualified to do this as you are. Nobody else has the big picture understanding, combined with the nitty-gritty knowledge of the mechanics of your company. 

"How can you send some young MBA “biz dev type” out into battle to sign up partners when you’ve never met with your potential business development collaborators and heard what their goals are and how you can meet them?  If you send out the biz dev guy I’m sure he/she will ink deals. That’s what they do. But you’re unlikely to yield results unless there is a close alignment of benefits for them and for you."

Mark wrote about biz dev deals, but the same principle applies to developing your outbound sales process. As a CEO/founder, nobody is as attuned to your business as you are - that's why you are the one who needs to do this. 

You Get Unfiltered Insights

Doing the grunt work is the price you pay for getting an unfiltered view of the marketplace. You need these first-hand experiences: the reactions of the prospects when you try to get their attention.

You need to hear with your own ears the words they speak when you pitch them.

You need to see their responses with your own eyes.

You need to understand what it takes to find a hundred quality leads, what works and what doesn't.


It's not good enough to rely on the interpretations your sales reps provide you with, because they don't see the full picture. They lack the context required to make the kinds of judgment calls which will shape your companies' outbound sales process.

When Can You Hand It Off To Someone Else?

Your ultimate goal is to build a scalable and repeatable sales process that doesn't require any handholing or personal attention from the CEO or founders - but that's exactly how you start out. You start out holding hands, you start out dedicating your personal attention to closing deals and figuring out how to make things work.

Once you transition from the sales exploration phase to the sales execution phase, then it's time to find a sales leader and let her take ownership of your sales operation. In wrote about the four stages of startup sales in my sales hiring post, and the transition point between sales exploration to sales execution is between stage #2 to stage #3.

Read More

Sales Mindset: How To Recover From a Bad Sales Call?

If you’re part of an inside sales team, this scenario is probably familiar to you:

You have a bad sales call; the person on the other end of the line is just rude and abuses you as an emotional punching bag. You hang up - and immediately vent your frustration: “Wow, I can’t believe this guy! Such an asshole!”

Another sales rep turns around and inquires: “What happened?” (The person asking that question is most often the person who not performing well that day either. When you’re on a roll, you’re focused to stay in the game.)

Now you’ve basically got an invitation to keep venting, and that’s exactly what you’ll do: “You know what this guy said? He said bla bla bla! Can you believe this?! So I told him bla bla bla, and then he bla bla bla! Total asshole!”

Other sales rep: “Yeah man, I had a call like this last week, screw these assholes, bla bla bla.”

Now the next sales rep joins the conversation, and soon you’ve transformed a bunch of sales champs into a congregation of complainers. The whole room is filled with negative energy.

And for what?

Just because your feelings were hurt when a sales call went bad. Congratulations, you’ve successfully brought down your entire team.

What should you do instead right after a really bad call?


What’s a better way to recover from shitty sales calls and bounce back?

First of all, step away from the desk. Get up from your chair, and get out of the room.

  • Take a five minute break.
  • Get a coffee.
  • Go for a walk around the building. Go outside, take some fresh air.

Get some distance from what just happened, so you can have perspective.

When you return to your desk, do something that’s fun. Just take a minute or two and listen to your favorite song, or read some motivational quotes, do something that lifts up your spirits and puts you into a positive emotional state.

And then get back into the ring. Pick up the phone and dial another number. Close the next deal. Focus on the work in front of you.

Don’t Put A Lid On Your Emotions

There is a time and place to talk about bad feelings. Don’t keep it all inside. You absolutely should have an outlet for the stress bad sales calls causes.

But do it in the right setting and at the right time. Have a framework for expressing emotions that leads to a productive outcome, rather than a destructive one.

It’s best to have a designated time and place, rather than just impulsively letting it out:

  • when you’re at lunch,
  • at team meetings,
  • have somebody in the sales team whom you regularly share your challenges and successes with - sometimes colleague can be the best coaches.

By creating a structure for this, you avoid carrying the negativity over into other sales calls (or even worse, your personal life).

Ask Yourself These Questions To Turn Bad Sales Calls Into Growth Opportunities

These questions direct your thoughts and feelings into a positive and productive direction:

  • How can I deal with people like this better?
  • What could I have said better?
  • How could i have managed the situation differently?
  • How could I have responded to the external and internal challenges better?
  • How can I deal with feeling bad?
  • How can I develop more emotional stability, and have more state control?

Come up with your own questions too, this isn't a complete list, it's just a starting point.

How Real Sales Pros Think Of Asshole-Customers

Remember that those jerks are the reason you even have a job.

If everybody would be easy, there would be no reason for companies to pay salespeople to bring them business.

If you can turn an asshole into a friend, if you can turn no into a yes, if you can turn rejection into affection… that’s when you’re great at sales!

Next time when you have a shitty sales call… don’t do the easy thing and use it as a reason to bring the entire team down. Instead, do the hard thing and turn it into an opportunity to become a better (sales) person.

Read More

This LOI Template Will Close Deals Quicker (Works for All Kinds of Contracts)

Are you in the final stages of negotiating a deal with a large customer or partner? And now you need to send over the paperwork?

Here’s a simple sales hack to get a LOI (Letter of Intent) template that will get signed quicker, and reduce the amount of legal hassle to a minimum. This works for a letter of intent, as well as other kinds of purchasing contracts, letters of agreement, term sheets, etc.

The Typical Way Of Crafting Contracts: Slow, Painful & Expensive


Even if you use a good LOI template, you’ll often find that it creates a lot of friction. Here’s what the typical process looks like:

  1. You download a template online and tweak it to your own needs with the help of your lawyer, or you use a friends’ LOI.
  2. You send your LOI to your customer.
  3. Your customer sends your LOI to their legal department.
  4. Their legal department will dissect your LOI as if they’re the CSI investigating a high-profile murder case. They’ll go over every line, every single word to make sure that it’s 100% waterproof. The legal department doesn’t care how long this takes. They just want this to be safe for the company to sign. They want to put themselves in as much a favorable legal position as possible. This can take a lot longer than you’d expect.
  5. Then they’ll make edits and comments, and send those back to your buyer.
  6. Your buyer will then send those over to you.
  7. You’ll adjust your wording according to their requests together with your lawyer.
  8. You send the revised LOI back to the buyer.
  9. They send it to legal again.
  10. This can go for several rounds…

It’s like a big legal ping pong match between lawyers. Very expensive, time-consuming and tiring. It can slow down your sales process considerably.

Wasting a lot of time in the contracting stage is something you want to avoid as much as possible. It can even starve a good deal to death, because during the weeks and months it takes a buyer to sign the damn thing something else comes up in their company that nips the deal in the bud, and makes it irrelevant for them. Keep the process moving forward. It’s too frustrating to lose a deal right in front of the finish line.

How to Get the Right LOI Template for Your Buyer?

Rather than trying to come up with a letter of intent in a vacuum, you ask them for one, and use that as your template!

Call up your buyer and say:

“Hey, can you share a letter of intent or a contract that you used in the last six to twelve months that was already approved by your legal department when buying something similar to our service or product? Have you bought something similar in the last year or two that went through procurement and legal and got checked off, got green-lighted?
If you have a deal like that, can you share that letter of intent or that contract with us?”

The buyer will send it over to you, and you have your perfect LOI template for this buyer. Just edit it to your needs.


The big advantage is that it’s pretty much already pre-approved. You’re using the wording their legal department is comfortable with.

You’ll get through their legal department a lot faster, they’ll sign sooner, and you can close the deal quicker. You get their money, and they get your solution earlier. And you can perform that favorite change in your sales CRM: change the lead status to "closed". Everybody is happy… except maybe the lawyers who are being paid by the hour ;).

Read More

What To Do When Your Prospect Doesn't Want To Switch Software?

When you're trying to get a prospect to drop their existing software vendor, and switch to your software instead, you'll almost always encounter resistance. How do you manage - and overcome - that resistance to switching software?

I'm going to assume that the software you're offering them actually serves their needs a lot better than the software they are currently using. So switching actually is in their best interest.

The Cost of Switching Software

Understand that the cost of switching is high - it's not just about how much their current software + service costs vs your offer, but also training, adapting new processes in the organization, and many other unquantifiable factors.

How Do You Get an Organization to Switch Software?

You're going to need 2 things to get an organization to switch:

  1. Patience and
  2. Follow-up.

That's doesn't sound exciting, cool, hip or new... but it's working. And that's all you should care about. 

The Nr. 1 Reason Why Organizations Don't Switch Software

Patience and follow-up help you to overcome the most common obstacle to getting them to switch software: bad timing.

Look at things from their perspective, and you'll understand why bad timing can make a deal almost impossible: They might just have gone through a 3-month long process of talking with different vendors, evaluating all the products in your market, the people involved in making the decision went through all these meetings, championed that software throughout the organization, got sign off on the budget, oversaw implementation... and then YOU call to pitch your software. 


There's no way they're going to switch to your product at that point, even if your product is 10 times better. The cost of switching to your software is currently higher than the value they'd gain from adopting your (better) software.

Be in for the Long Haul

So you need to acknowledge that this isn't the right time, and adapt a long-term approach. The time it takes to close this deal isn't measured in weeks, but in months. Think 6 to 18 months to get them to switch software.

That shouldn't bother you - that should excite you. You're building a pipeline of great, high-value leads that you can close next year. This is an opportunity to build a relationship with them and get to know them better and learn about their sales process.

Systematize Your Follow Up

Follow up with your prospect every month or every quarter via email or with a quick call. Stay on top of their mind (in a positive way). Just by following up consistently, you build a certain level of trust. 

If you're managing more than 100 leads, you'll need some kind of sales pipeline management software to stay organized.

Be Ready When the Day Comes

When their current contract runs out, or there's another change in the organization where the barriers to switching software are lowered, they'll remember you. And they have just spoken with you a few weeks ago. You already have a relationship with them and they know you. You've invested months to position yourself favorably - it's time for the right hook.

How to Decide if a Prospect is Worth Investing That Much Time In?

Of course you don't want to waste a lot of time on prospects who will never close. Being perpetually stuck in "I'm working on my pipeline"-land is the sign of lousy sales people. 

Here's what to go by: Are the prospects problems a good fit for your product? If their wants and needs match what your software really excels at, then keep following up with them even if the likelihood of them buying is currently very low.

The other question to ask is how much is this customer worth to your business? If it's not in the thousands of dollars it will be hard to justify that much follow up from a economical point of view.

On the other hand, a prospect who is showing some buying signals, but isn't really a good fit for your product (even though they're interested in buying)... then they're probably not worth following up with all that time.

Read More

Call Transferring

We're excited to announce the launch of call transferring which is available right now for both inbound and outbound calls for those on our Business and Enterprise offering.

Once on a call, you'll notice the transfer icon. Each user with an eligible plan will be displayed in the drop down next to an online/offline marker indicating if they have their Close.io application open and are available to take calls.  Simply click on the team member to whom the call should be transferred -- your call will be hung up and they will receive an incoming call displaying the correct caller id and that you're the person transferring the call:

Here's a quick example of the current call transfer drop down and user availability indicators:



The incoming calls to the person you transferred the call to looks like this:



And here's an example of the call activity generated when a transfer takes place:



For more informaton about this feature, checkout the call transferring help article.


Happy calling!

Read More

The Partnership Hack - Never Miss Great Opportunities, Never Waste Time On Worthless Deals

One of the most precious resources for you as an entrepreneur is your time.

What’s one of the biggest time-suckers in business?


The more successful your company becomes, the more offers for partnerships you get.

  • People offering to sell your product for you
  • People offering to promote your product as an affiliate
  • People who offer to distribute your product
  • People who want to re-sell your product to a different market
  • People who have the perfect up-sell for your customers and suggest a revenue-share.

On the surface, this is a good thing, right? People want to help you grow your business faster.

Most Partnership Proposals Suck

But once you actually respond and engage with these people, you'll find that it's just a big waste of:

  • time,
  • money,
  • mindshare,
  • equity.

The Opportunity Cost of Lost Time

If you pursue and engage with these people who propose partnerships to you, you won't have time to run your business anymore. Following up with these people, setting up long meetings, negotiating details of a deal and putting together contracts.

The Fear of Missing Out

While *most* partnerships suck, *some* can catapult your business into an entirely different stratosphere. You don't want to miss out on a deal that could grow your business 10x.

How to Solve This Dilemma?

There is a simple way to not miss out on a potentially great partnership, and at the same time not waste your precious time on worthless negotiations.

The Simple Reply Email

Just send them this simple email template that almost magically takes care of this for you:

thank you so much. I appreciate the offer. We feel honored that you're reaching out, and want to partner with us.

Right now, we're heads down in execution mode, and we don't have any partnership agreements in place, but here's how we typically like to work with others.

If you honestly think that this could be a good fit, and you have lots and lots of potential customers for us, why dont you close one deal to get us started? 

That would prove to both you and us that there is real potential here for a partnership. We're happy to compensate you for that one deal, no problem.

And once you brought that one new customer we'll take the data of that result, and we'll jump on a call to discuss it further, and take it from there.

Sound fair enough?


I have done this hundreds of times now. I've told people: "Hey, we don't typically do partnerships, but bring us some customers. After you've brought them, I'll be happy to pay you some money, and then we can talk about how and if we can expand this into a full-blown partnership."

I literally did this HUNDREDS OF TIMES.

Every single time, the reply I get is: "Awesome! Sounds like a great deal! Look out for all the customers that I'm going to bring you! This is going to be huge!"

What happens next?





Not a single time did someone ever follow up delivering a result.

This saves me shitloads of time. I don't have to evaluate anything. I don't have to meet with them. I don't have to check their background. I don't have to worry that I might have said "no" to somebody that might have been a great opportunity. I'm free to focus on what really matters to me: building the best sales software on the market, and helping entrepreneurs to make more sales and close more deals.

If there really is potential for a great partnership, and if they can truly deliver results... they will! And then we can take these results as the basis for further decisions and discussions.

If you're a startup don't waste time on partnerships. Only consider that once someone has actually delivered results for you.


Read More

Subscribe to Blog Updates

Posts by Topic

see all

Follow Me