Let’s keep selling through this.  Our commitment to you in these uncertain times →
FourSquare sales for startups event

FourSquare sales for startups event

You'll enjoy this startup sales workshop Steli gave in New York, organized by Eric Friedman, Global Senior Director of Sales and Revenue Operations at Foursquare along with Dave Greenberger and Evan Bartlett. Eric is putting these Building the Sales Machine events together regularly, so if you're a sales superstar in NYC, check out his website.

Prefer to listen? Here's the audio-only version:


Eric: All right, everybody. Good evening and welcome to another Building the Sales Machine event. Tonight’s special guest is Steli Efti, who’s the CEO and Founder of Close. Welcome Steli. [Applause]

Steli: Hey guys.

Eric: So first of all, thanks everybody for coming out. My name is Eric Friedman. I’m on the sales team at Foursquare. Big thanks to my co-hosts, Dave Greenberger and Evan Bartlett, for throwing this event with me.

Thanks all you guys for coming out. You guys have been identified or self-selected as the sales leaders in management in the New York City startup scene. So thanks everybody for coming out. What we’re going to go through tonight, thanks to some questions we prepared ahead of time for Steli and questions from the audience, is the things that are on everybody’s mind.

But before we get started, I want to introduce Steli, who is an entrepreneur and a self-described unemployable person who went and founded his own startup built out of ElasticSales, building his own software as a solution, as a monthly sales product for startups, of which Foursquare is a happy customer.

Steli: We love you guys.

Eric: And wanted to welcome him to the Foursquare stage. Thanks for coming out Steli.

Steli: Thanks for having me.


Eric: Yeah, thank you. So with that, I’m going to go into a couple of questions we prepared and then jump right into questions from the audience, and then take questions from you guys if I don’t get to one of your cards. We’re going to do this for about a half hour, 45 minutes or so, and then give you guys a chance to hang out with Steli in the end and maybe do some breakout sessions on meeting the people that ask good questions from the audience and spending more time on the things you guys want to talk about as different groups.

We try to cut the fluff from a lot of our events. That’s why we’re skipping a lot of the background. So with that, I will just dive right in. Cool.

When should you start using sales software?

Eric: So a big question that we spend some time on, when do you know to use technology and software to solve sales problems versus good old-fashioned elbow grease and hard work?

Steli: I think it’s a good idea to – just a general rule, it’s a good idea to do these things late, right? So there are things that are essential, like talking to customers, closing deals, actually creating outcomes. It doesn’t matter if it’s a deal that didn’t work or deal that worked, but creating outcomes, getting some traction on the street, actually going out there and basically leaving your bubble, office, whatever it is, and actually interacting with the real world. That should always be priority number one.

Then whenever the pain is so strong that you can’t take it anymore, that’s usually the right time to actually fix the problem. Not way in advance. We don’t have any customers. We don’t have any leads in the system. We don’t have any salespeople. But let’s spend the next month actually researching the CRM market. We made a massive spreadsheet and we’ve done some market research. That’s not your job, right?

The job is not to select the best software in the world. Your job is to get out there and actually create value and get customers.

So late would be one advice. A little unnatural from a guy that sells sales software but late. We tell people, hey, if you don’t have at least 100 leads per year that you work with, if you don’t actually do a lot of calls, a lot of email, just use a whiteboard, piece of paper, like something, a spreadsheet. Just get started as low tech as possible.

Once it becomes a real pain, eventually you go out there and you find a solution.

Outsourcing or insourcing sales?

Eric: So what about outsourcing sales versus insourcing sales? A lot of these folks are getting started. Maybe some people are scaling up their sales team for the first time. They have those first hundred leads. What about outsourcing that sales effort versus building it up in-house especially as you’re just getting started?

Steli: Yeah, late is the advice there. This is going to be the takeaway for the evening. Start everything late. All right? So we ran an outsource sales team. We did sales for over 200 venture-backed startups in Silicon Valley.

Here’s the number one problem. A lot of companies, they go out there and seek help from kind of an outsource firm. They do that too early. They do that because they’re seeking help because they can’t figure it out.

That’s not the right time to seek out help. Yes, you need help. We can figure it out, how we’re going to figure it out. Yes, bring people in. Advisers, investors, other peers that have solved their problem before you and get their advice; but then find a way to actually execute on that and create the outcomes that you want.  You can’t outsource problem solving, right?

I mean you would never think of going to a firm that develops iPhone apps and say, “I want to create a company and I want to have an app, and the app should be a productivity app. Go and make something happen for me.”

That doesn’t seem specific enough. The same way you don’t want to go to an outsourcing firm and say, “Well, we know we could sell to restaurants. We haven’t figured out how to actually do lead gen, how to qualify these restaurants, and how to sell them effectively. But why don’t you go and do that for us? That will be kind of awesome.”

Everybody gets why that’s awesome. But the reason that doesn’t work is that the outsource firm is not going to create those outcomes or learnings for you.

Even if they do, you don’t want that. You want that core knowledge and skill base to be internal.

Once you’ve figured out something and you really can predictably repeatably create it, if you know how to actually do lead gen, and you do it every month and you know exactly what you’re doing, then you can look for outsourcing firms in order to scale that at a lower unit cost or get it at a faster pace.

But if you’re still in the, what I call sales exploration phase in the specific area, when you’re still trying to figure out how to make this work, you need to figure that out on your own.

You can get help from the outside, but you need to build that skill set and knowledge set internally. It’s not the right time to outsource.

Tips and pitfalls for developing your first sales process

Eric: I know one of your big themes from talks I’ve seen and something that’s important to you are like the sales hacks and tips and tricks that people aren’t doing. But maybe before we get to that question, you’ve seen a ton of companies who are starting their sales process for the first time. You’ve consulted with a bunch that are doing the same and probably seen them grown into pretty sizable organizations. I would love to hear maybe the top things that they’re doing well and more importantly the things that they’re not doing well that you keep seeing over and over and over that makes sales teams stumble.

Steli: Yeah, it’s a great question. So I think the teams overall that are doing well are good at focusing at what matters.

So if you’re in a startup, 90 percent of the time, everything is going to suck or most things will suck.

Not the first week. The first month or so, you’re going to be like, “This is so exciting! I love this! Entrepreneurship! Yeah!” You watch The Social Network every night and like pumps me up for the day and that’s awesome and that’s beautiful. That kind of energy is useful. You can channel that into helping the company.

But eventually you start seeing everything that’s wrong with everything. You see like the team is fucked. The product is fucked. Our funding is fucked. Just like everything here is wrong.

Welcome to the real world.

Everybody is in the same boat.

That’s one of the craziest things. I’ve yet to meet a startup, no matter how successful, that doesn’t feel like everything is wrong about them.

But the teams that do well are not being slowed down by that, by the messiness of the startup, and they’re not being distracted by kind of the, “Oh, what could we do that will make us look successful? How can I act as if I’m successful? How can we pretend that things are going right?” But are really like focused on the things that truly really matter and in – for most people here, what really matters is customers, right? Revenue and customers, and maybe once you talk to enough potential customers, you figure out what we’re doing will never work. We need to do something else to help these customers or to make these people customers.

But the companies that do well, they suck at most things, but they just are not distracted or slowed down by that.

Then kind of pitfalls is really getting distracted, trying to over-optimize. Like this effectiveness versus efficiency, like trying to do something really perfectly well versus trying to only do the thing that really matters.

Like, I’m always amazed. There are so many entrepreneurs out there and VPs of Sales and Sales Directors and hustlers out there that are crushing it. They’re not particularly smart - I’m one of them - that are not like super talented in any way. But they’re just really focused on what matters and they just never stop.

Then there are these other groups of people that are highly intelligent, highly well-educated, really incredibly talented and they’re not crushing it and it’s because they’re like so distracted by everything. They’re trying to optimize on things that – at the end of the day, they don’t really matter.

So prioritization and prioritization, not being slowed down by the messiness of things is probably a key thing.

How to keep your sales team focused?

Eric: So we like to keep things very tactical. So I will put you on the spot a bit as a CEO. How do you keep your salespeople with keeping their eye on the ball, away from the funding news, the marketing news, the other distractions that are out there? How can these guys take lead maybe from your example and how do you keep them from getting distracted by those things?

Steli: It’s really hard. I don’t have a perfect formula for this. But I can tell you that every time we struggle, every time it feels like this is harder than it should be, and when I can just tell the team, the company, individual performance – you can just read it in the body language. Everybody is just struggling. Your work is harder than it’s supposed to be.

We step back and I try to figure out what are all the things that we’re trying to do as bullshit.

What are the core things that truly matter?

More often than not, that’s the really hard part because a lot of them seem like really important things. So it’s the constantly cutting back on the list, simplifying. What is the core thing we should be focusing on?

Then what happens is you cut down the list to a few essentials and then the team starts crushing it again and the numbers go up and everything is fucking awesome.

Then what happens is just like feature creep in product. People are like, “Well, we should also try this. We should also go after this vertical. Well, we should also integrate this software. We should hire more people to try out this. We’ve never actually done that.” The complexity of things starts to increase. It slows down the team. People start getting stressed out and then it’s a good reminder for holy shit, we should cut back on what we’re doing and focus on the essentials.

What activities should salespeople focus on?

Eric: So I know that we could probably talk just about – have a whole session on this. But on those tips and hacks and those things that you think people should be spending their time on, maybe share the top two or maybe even three that you think are most critical for successful salespeople.

Steli: Well, for successful salespeople, I will just share one, right? We will simplify this. So the number one thing that I consistently get feedback from people that really made a difference, all the way from like an individual salesperson, it’s like “This is my first day in sales. This was a really valuable lesson,” all the way to like a venture capitalist that has like sold three companies for hundreds of millions and said, “This was the most important thing I’ve ever learned from you.” It has been the follow-up.

So I have a very simple strategy when it comes to follow-up and some people that know my stuff know this, but it never gets old.  So I’m going to talk a little bit about that. So I truly believe that 90 percent of winning happens in the follow-up and follow-through.

Showing up is difficult enough, but even more difficult for people is actually to follow-up and follow-through really consistently and where I see most deals are lost, most opportunities are lost is by people just simply not following up enough. So I have a very simple follow-up strategy.

I follow up – if we ever had a successful connection, if we actually have a call, a meeting, you ever reply to an email of mine. If I called, emailed you, and never heard from you, it’s different.

I might follow up three or four times. The last email might just be a breakup email saying, “This is the last time you hear from me. I will take it you don’t want to talk to me. So if you ever want something from me, you can get back to me,” and people respond to that email really well.

But three to four follow-ups when I’ve never heard from somebody. But if I ever heard from you or we ever had a meeting or call, I will follow up indefinitely.

That means forever. I will never stop ever, ever stop following up just ever. Forever, right? I want to make this clear.

I will never, ever stop following up with you and I will not waste any time or energy making up a story for why you’re not replying. I’m not in the mind-reading business. I’m not going to make up like a – oh, this gal doesn’t really like me. My shoes were ugly and they think the presentation is this. No, I’m just going to keep following up.

I’m not going to be needy in my follow-up. My follow-up is not going to be like, “Why haven’t you replied to my email? I really think that’s kind of rude.”

I have people send me like an email and three hours later complain that I haven’t replied yet. Whoa! This starts out too needy and intense for me.

No, it’s just going to be like email 40 will be, “Hey, another beautiful day in paradise. I hope you’re doing well. Here is some great news about our company. Can we talk this Tuesday at 10:00 AM?”  Then email number 80 will be, “Hey, another great day in California. Well, how about this Thursday or Friday, this or that time?” and I shared a couple of stories.

There are so many wins that I can mention but I will just mention one. One of our investors got us in touch with this uber billionaire person that built something you’ve all used before. The guy actually replied and said, “Oh yeah, I want to meet with you guys.”

So we got excited. I replied. I suggested a few dates and times, didn’t hear back. Replied again, didn’t hear back. Sent another email, didn’t hear back.

Forty-eight emails later, 48 emails later, his reply was, “Oh my god! I’m so glad you followed up, Steli. I was like traveling. We had this crisis. Here sharp tomorrow at 1:00 PM in our office,” and they invested.

That’s just one. I have so many examples and since I’ve been starting to preach the gospel of the follow-up, there are like so many people that come up to me at events and are like, “I just closed a $100,000 deal and that was the 30th email.” There are all these stories of people that suggest that if you actually get your follow-up game up, you can win.

You’re going to be competing with nobody else because everybody else will stop following up. If you only take one thing away, just double the amount of follow-up that you typically do after today and I think the world is going to be a better place.

About the sales CRMs and marketing automation software

Eric: Love to get your thoughts on the changing landscape of the CRM market, the marketing automation companies that are moving into that market. There are kind of blurred lines between the utilities that are out there for lead funnels, contacting people, moving into your game of CRM. What do you think about those blurred lines and where do you sort of separate the tools that you should be using?

Steli: That’s a great question. So I’m super biased, but I learned last week – we went to Inbound and we learned that just because I’m biased doesn’t mean I’m wrong. So I’m going to use that line. That’s a good line.

So from my perspective, there are – there are kind of – there are companies that try to do everything and be everything to everyone. Typically those companies are really great at the enterprise level, where that level of like massive integration with just everything under the universe is required.

Then there’s like this rise of new applications, especially there’s – it’s an exciting time for salespeople because for the very first time in the history of humanity, there have been more and more sales apps that are actually somewhat usable and you could imagine that a person with some level of empathy and knowledge about sales actually worked on this.

So I think that’s a good time to be in sales. I think there’s some really cool stuff out there.

There are a lot of sales apps that we believe that didn’t – maybe not quite ballsy enough to go and say, “Well, here’s an area of sales we really understand. We’re going to build something for that,” and went more like, “What’s a tiny thing that we can sell where we don’t have to convince you of changing what you’re doing?”

We went the other way around just by accident because we didn’t plan on selling the software. So we just built something that was great for us and our use case was unique because we were doing sales for so many different companies.  So I don’t know. I don’t have a great answer for like the companies that do – that connect marketing automation with CRM, with success, with support, with all these things, versus the companies that offer very specific, unique apps.

But I think that overall, simple is usually better. It’s a general rule that I like.

So most companies that we see do a really great job with the sales stack they have, they’ve chosen a few applications that they use and they use those – they commit fully to them. So they use them well. They train their people to use them well. They have some discipline about using them well and they see great results.

How to make sure people study the sales materials you send them?

Eric: I want to switch gears now and go to some questions from the audience, that they wrote down in their respective table groups. Again, thanks everybody for submitting these. How do you ensure that people you are going to go in and meet with or you’ve set up a call with or you’re going to present to have done the homework ahead of time, have seen what you’ve sent over, have known enough about the product for that second or third level follow-up call?

Steli: So it’s a great question, so two things. Number one, assume they won’t because homework sucks. Just assume they won’t. So either you can actually figure out a way to make this work without people actually checking out your stuff beforehand or at least don’t have the expectation.

It surprises me to see salespeople surprised by the same thing every single day. It seems kind of like weird.  You’re surprised once but then eventually you should be prepared for it.

So find a way to just accept, embrace the reality and go into the conversation not with like some awkward, “Well, I sent you over the material. Did you have a chance to check it out?” - "No, you know, this was a really busy week." Now you make them feel bad and they will apologize. "Oh, yeah. Well, let’s then maybe – you know what? Maybe – should we just go over that material right now?" This is awkward. This is awkward.

It should just be like a – if you can change that fact, you should just embrace it and be like, “All right. Let me guess. You didn’t have time this week to check over the material.” - "Oh no, I checked over the material." - "Oh, great!" Now I can actually like praise you. This is awesome. You get three brownie points and like we’re going to send you a big hat and a T-shirt, whatever it is.

If they say no, it’s fine. It’s normal. Say, “You know what? That’s totally normal. Here’s what we’re going to do next. We’re going to pick up the really important things out of that.”

One maybe tiny hack that I’m going to throw out there that you might try, not like very early on in the sales cycle; more later down the sales cycle. But something that I have done successfully in a different setup was with larger customers at the end, just before they were ready to buy, would actually tell them, “I’m not going to allow you to buy, before I can make sure that you actually know your shit. So here’s a ton of information about this.”

What I was actually doing is preparing them not to churn, because I knew that these people will interact with other people that would ask them difficult questions that they didn’t have good answers for. Then I would have to actually go and try to save it.

So in preparation of that, I would give them homework and tell them, “I’m only going to allow you to buy if you actually study this material.

Next week, we’re going to go through this. I’m going to test you. If you pass, I’m going to allow you to buy.” It’s a nice little change of dynamic there.

Then you don’t go in and you go, “Here’s my 10 questions.” If they’re not able to answer, you’re like, “You haven’t passed. Bad boy.” No, you help them. You help them cheat. You go, you know what, did you – OK, so first question is this. What would you say? When they struggle, you kind of – you know, and you give them the answer, right? Just help them out here a little bit. But overall, accept and embrace that fact.

Don’t make it awkward and if it’s a bigger sale, you might want to do a little bit – actually use that to your advantage to prepare them to be able to defend the product and the purchase with other people.

Eric: I’m going to pull on that and throw out a little bit of churn because I know it’s such an important topic to us and a lot of the folks in this audience. Has that been effective for you and how has that loaded or even decrease churn? Is that an effective method?

Steli: So that method was super effective because what I was actually doing was coaching people how to react and giving them like the muscle to actually react well. So what would happen is a lot of times these clients and customers would actually call back and go, “Steli, I just had a meeting with this and this and they asked me that stupid question.” I said – well, now I’m proud of them to become really heroes, look really good. Feel great about it. That’s exactly what you want your champions to be.

That only came about from like selling complex sales and then having to go back and save it.

Like all of a sudden, they would have regret and say, “Well, I change my mind. We have to cancel this.” You would be like, “What? What happened?” and it would take so much effort to figure out that was somebody that asked a stupid question. That’s all it takes sometimes. So this was an effective strategy at the time.

We’re not really doing this for Close. We might. We maybe should be with some larger customers. So much advice that I give them, like I might want to follow that on myself. So we’re not really like – it’s not part of our process today. We might want to do that with larger customers. But back then, it made a big difference.

How much does customer feedback impact Close's product development roadmap?

Eric: A couple of people asked a variant of this question but you must get a ton of product feedback both from current customers, from new customers asking to build this feature and then we will buy or maybe customers that have churn. How much does a customer feedback cycle impact your product development roadmap?

Steli: A good question. It’s hard to say. Like the way we go about these things is we listen. We try to actually truly understand, so not just stay on the surface level of things but actually go deep.

Well, I need this button. Like a lot of times I see salespeople and a customer will give product feedback like, “It would be great if you guys had some marketing automation included in Close,” and the salesperson would go, “Yeah, that’s definitely something interesting. Maybe something we will do down the line. It’s definitely on our roadmap.”

Wait a second. What does marketing automation mean to you? What exactly are we talking about? Is it the newsletter? Is it drip emails? What exactly do you want? Why do you want that? How do you solve that problem today? Why would you want to solve that problem in the concept of Close? Truly actually understanding what’s behind that request is really important.

Then you might solve it the way that the customer suggested. You might solve it totally different.

But you want to understand what’s behind the request because people are great at – people are awesome and customers are great at knowing what their pain points are. But they’re not always great at telling you exactly how to solve them.

Then we don’t really – we’re not super analytical about keeping track of every single customer’s request and what they say and how they say it.

But we go by a very simple philosophy of like we just – everybody in the company interacts with customers. Everybody – it doesn’t matter if you’re the founder or an engineer. Whatever you do, everybody interacts with customers.  So we all have a pretty good pulse and the things that are the biggest pain points or the things that we see are the biggest opportunities are the things we go after usually.

How do you fit doing customer support in your busy schedule?

Eric: This is a great segue. You said everyone participates on that level. I know I’ve seen it and the question is – we’ve seen you participating in the customer support chat that’s just live on the site. So how do you keep that in your day to day activities? What do your day to day activities look like? How do you stay that involved to actually be in a support channel online for prospective customers just throwing questions at you?

Steli: Yeah, it’s a great question. So one way to do it is being small, like the – when we were doing ElasticSales and doing outsource sales, we were a larger organization, multiple people. So my days were very much like managing clients, closing big deals, putting out fires, hiring, recruiting, all that.

With Close, we stayed like super small to probably the – somebody said the other day – we had a team retreat and went to Vegas and somebody in the team said, “We are the only CRM that’s small enough that would fit in one Uber but it’s not coordinated enough to actually make it happen.” We actually had two Ubers to the airport. So we’re a super small team.

That’s number one, and we work really hard to stay small. The reason is because we love profitability. We think that’s the best kind of capital. So we like to automate a lot of things, find ways to do things at a level that most of our competitors are much larger.

In terms of just like my involvement in like customer support or talking to customers or being involved in sales or anything else like that, I truly believe that everybody in the company needs to be as close as possible to customers. Everybody. So for me, one thing that I do for instance is I do sales office hour.

So I will have a bunch of spots in my calendar and all our customers and all the people that read our blog and interact with our content could just go into the calendar and pick a 15-minute spot and just get my time and attention. Usually those spots are not like sales calls. Those are like here’s what’s – our problem with our sales process and then I will just give advice.

That has been like a great engine for us, for marketing, PR, word of mouth. It’s a great engine for ideas for content, like that’s how we – I get most of my ideas for what blogs to write and what things to talk about.

It’s a great differentiator. It makes us different. It makes us standout and it also allows me to understand my customers better, which is a good thing. So we truly believe in like support needs to be a core thing.

Our engineers are all giving support. They need to feel the pain of the customer. They really need to feel that pain. They can’t just outsource that pain to some group somewhere, so yeah.

How to sell to enterprise clients?

Eric: Maybe through the lens of both Elastic and Close, just to get hyper-tactical because I know this group cares about these things a lot. How do you go about selling to enterprise clients both from the consulting side, from previously, and then now as prospective SaaS customers?

Steli: So a couple of things. I think that number one, you truly need to understand that there’s no such thing as selling to a logo. A logo doesn’t buy things. It’s human beings and the difference between selling an enterprise company versus a restaurant is the amount of people that are involved in their incentives and the way they do things. So you never sell to Coca-Cola. You sell to John.

You need to understand who is this person. What does this person need? What do they care about?

People are always I think surprised that the individual motivations and goals are not always perfectly aligned with the overall department or company goals. So you have to be sensitive for that.

You need to understand what does the company need to accomplish. What does that department need to accomplish? What does the individual need to accomplish?

Sometimes the individual’s incentive might be more about looking good, right? And making choices that are safe versus making the most progressive, most – highest ROI possible choices for the company because that might be too risky for the individual.

So you need to understand who am I selling to. What is this person’s motivation?

In enterprise sales usually you never sell to one person alone. You might have one champion but that champion now needs to go and sell somebody else. That person needs to go and sell somebody else. That’s what makes this slow and complicated. Your job is to actually try to understand as much as possible about all these people and give all of them a different reason, a version, a customized version for why they want to green light this deal.

I think if you understand that, enterprise sales becomes less mythical and it’s more practical. Oh, I don’t sell to one person. I sell to five and they don’t all want the same thing. They don’t all speak the same language. So I need to have a little bit of flexibility and work with this group to make this happen.

When should sales reps should hand over customers to account managers?

Eric: What do you think is the right mix between – once the sale is made, bringing in or shipping things over to an account management team, bringing that salesperson back or just leaving the upsell, resell, renewal with the account management team. Maybe how do you guys handle it? What have you seen as a successful mix of the two?

Steli: Yeah, I don’t have any specific – I’m not dogmatic about that or I don’t have one way that I think is the best way. I’ve seen all kinds of different scenarios work for companies successfully.

I think it’s very much like a, “Who are you selling to? What’s the culture within the team? What’s the best setup for that individual team?” So I think both can work.

I’ve seen companies that have their salespeople actually take over an account management role and success roles.

I’ve seen companies that have more of an assembly line process where once the deal is closed, it moves over to somebody that now takes care of that customer. I’ve seen – we discussed this earlier today, like the part system where you will have teams of like maybe two sales development reps, two account managers and a support and success person. They all stay with the customers and they’re just one team. Then every customer that has been [0:29:28] [Indiscernible] stays within that team, that – I don’t really care for us because we’re so small.

We don’t have like a huge assembly line of people and to push people over. So our sales reps, when they close a deal, they take care of their customer. But then I might take care of you. Somebody else might step in, so yeah.

How to keep salespeople motivated each and every day?

Eric: We talked a little bit about motivation earlier and I know motivating local sellers and folks that are doing lots and lots of cold calls every day is critical, both the sales managers and the people on the phones. We have a mix of both today. What do you think are some of the best ways to keep those people motivated and keep them with that same effort and hustle on every call every day, week over week, month over month?

Steli: I really truly believe that the way to greatness in sales is consistency because it’s fucking hard to be consistent. I think that what makes – like sports is a really great – I’ve never been like doing any sports in my life.

Sports is a great – seems like a great metaphor for this because if you’re Michael Jordan at the prime of your game, you’re not coming on the field and they go, “Well, this is Michael Jordan, 30 points advance to start off the game, because this is fucking Michael Jordan.”

No, it’s zero. It doesn’t matter what you did last month, last year, last decade. Come to the field. It’s a new game. You start at zero. Oh, you had a bad day today? You had a fight with your – it doesn’t fucking matter. It’s zero. Perform right now. Every single day.

It’s also not like, “Oh, you’re Michael Jordan. You don’t have to do any training anymore. You surely know how to play basketball, right? What can I teach you about that? Just fucking stay home.”  No, that’s how it works, right? He’s the guy that trained harder than everyone else.

I think people coming into sales need to understand that that’s going to be the reality that you live in, especially if you do a lot of like cold call high volume outreach.

I think one way to motivate people is to make them understand what is the game that you’re playing. This is not like you’re going to suffer through it a little bit and then once you’re going to be good, this is going to be easy. No.

Also what is good? A lot of people, a lot of sales orgs, reward people that were particularly creative and charismatic in the way they close something or had a particularly amazing day and then everybody kind of idolizes that day and the deal they closed, how awesome they said something.

I would really over-proportionally reward consistency. Really like who brings it every day, every single day, really every day. Like no matter how shitty everything else is, they still come and they bring it. Those are your heroes. Those are the guys and gals that are fucking crushing it. They will need to be the role models for everybody else. So I think that’s one big part.

The other thing is like if you’re not sold on your own shit, you can’t sell anybody. That’s why new people are always great at the beginning because they’re so sold on it. They’re so excited about everything and then once you look behind the curtain, you start becoming more critical and it kind of affects your ability to sell.

So I think with sales teams in general, it’s a good idea to have rituals that help everybody be resold on why is what we’re doing awesome. Why is what we’re doing important? Why are we fucking amazing? Because we really all need to be reminded of that every day because it’s easy to forget. I think those are two main takeaways there.

How to recruit great salespeople?

Eric: Great. I’m going to ask you just one more question and then warm up the audience. I’m going to take questions from the audience after this last question for Steli. So get your questions ready and we will repeat them up here. So, on that note, recruiting, top of everyone’s mind, getting in good people. Common theme throughout a lot of the questions I saw. How do you recruit the best and what do you think are the attributes that you look for in that first interview, that first phone screen or that first hand-off to the rest of your team when they’re ready to interview that person?

Steli: It’s a great question. So I think two things. One, you don’t – I think the greatest hires I’ve ever made, the greatest hires I see other people make are not necessarily coming from the obvious places. They come from easy places that are not obvious.

So who here grew up as a small child dreaming about one day being a salesperson? Like just a show of hands. There you go. That’s my man.

Eric: One person.

Steli: So one person. You’re the one person I’ve ever met that said that. All right. How old were you when you knew this was going to be your career? You’re weird. You’re just super weird. All right. Everybody else is healthy, normal. I congratulate you. You’re a little on the weird side. But it’s also good. It’s fine. All right, worked out for you.

Most people I know, they didn’t necessarily want to be in sales. It’s not like a career everybody is like idolizing. So a lot of times, people that could be fucking amazing at sales don’t know it and aren’t looking for opportunities there.

So a lot of times I think when you’re hiring, if you take the lens of not just going, “Where are people that want sales jobs? Let me go there and like make my pitch and recruit out of that pool,” but instead go, “Where are people that don’t fucking want sales jobs that would be awesome at sales?”  Let me go – because if you go over there, you’re alone. You’re the only one recruiting.

So a lot of times when we hire people at ElasticSales, first day when we hire them, we ask them, “Hey, who’s the smartest person you know that would never ever even consider for a minute working here? Who’s somebody that we have no chance of hiring?” That’s the fucking person I want to talk to next.

We would call these people and tell them. “Hey, John said you’re the smartest person he knows. He said you would never work here. So I’m not going to even try that. I just want to get to know you. I love talking to smart people.” That’s the recruiting call. That worked out pretty well for us.

So a lot of times, it’s kind of the – instead of making a – I have a sales job for you and although you’re not looking for a sales job, here’s the job offer. That’s not going to work well. It’s more of a gradually falling in love with each other and with the opportunity.

So it would be like let’s get to know each other and then let’s get to know about what we’re trying to accomplish. Hey, this is so great. Why don’t you just stop by and meet the team? Let’s all get to know – and then eventually you drop in. Like, hey, I’m kind of trying to recruit you but not really, but kind of a little bit. But it’s fine if not.

Then slowly but surely you see they’re falling in love. They’re leaning in on the opportunity and slowly they start selling themselves and like "Yeah, I mean sales, I didn’t really want it. But this company, the culture, the opportunity, and if I look at it this way, this is actually great."  So that’s a great way to hire amazing people.

What was the second part of the question? I don’t remember.

Eric: Retaining those people or just – I mean I think that’s a great answer but bringing those people in once you identify them.

How to evaluate new sales hires

Steli: Oh. I think the second thing that I wanted to share with you guys is I think going back to consistency, I don’t assume – as long as I haven’t seen you perform consistently especially in days where there were reasons not to, I’m not going to make up my mind that you are amazing or great. I’m going to coach my team to not do the same thing.

So there’s a lot of times – some people are so fucking awesome at interviewing. They’re just fucking interviewing rock stars. It’s hard – more or less, you learn to become really good and calibrated on your bullshit meter. But some people are just too good.  So they might even bullshit you and some people are good at performing under pressure the first week or the first month. But that doesn’t mean that they’re amazing.

I think people make – in sales, it’s too easy. I see teams in leadership make judgment calls: "Oh my god! We have a rock star." - "Oh, cool. How long has he been rock starring for you?" - "Three days. All right. Let’s lean back. Let’s take a breath and wait for a little longer, right?"

I love to like celebrate rock stars but they need to prove themselves consistently. So I think that’s a good practice because it’s kind of hard if you bring people in and you praise them too dramatically to everybody. Then everybody goes, “Oh, this is what we’re trying to accomplish here,” just like being amazing for a day and then two weeks later, everybody is like, “Oh, this person is like not that great and creating all this friction.”

That’s what makes it suck to hire lots of people and bring them into your organization. So being disciplined about it, like taking a moment to judge people is a good thing I think culturally.

Eric: Great stuff. Maybe we will take a couple of questions from the audience, make sure we hit on everybody’s notes they wanted to ask Steli about.

[Participant raises a question]

How to train new salespeople on the product

Eric: So the question is training on sales, training on the product. What’s the third one? Or both. What gets the priority and what do you think is the best mix of those?

Steli: That’s a good question. So I mean you have to do both but the question is, “How much?” Again, like prioritizing, not for efficiency, for effectiveness. So a person – a new salesperson doesn’t have to answer all possible questions. It’s not the right training. Like all right, you just join. We have this massive big data analytics platform that we sell to Fortune 500 companies and you’re 21. So we’re going to spend the next six months training you. It makes no sense.

So I think that giving people a good understanding of here’s how the product works, here’s why it’s creating value and by the way, here are the top 20 questions you’re going to hear every fucking day. Let me train you on how to answer these questions, like the top, not the long tail. The top of the tail.  That’s good common sense.

You can do that in a few days and get somebody comfortable answering the first few questions. With ElasticSales, we did sales for so many different companies. What we trained salespeople to do when they encounter a question they couldn’t answer is just be reasonable.

Tell the person. Don’t bullshit. Like salespeople have this like, “I need to look good.” Oh, yeah, of course we can do this. I guess we could do everything. We’re amazing.

No, you just train your people to say, “It’s a great question. I don’t have the answer for you. But I will get the right answer to you and get it back. Now let me ask you. What would you want the perfect answer to be? What would you want me to come back with in an ideal world and why?”

Because again, I see people – we’ve trained people to do that and they came back and they’re like, “They need the marketing automation button,” and then the engineer goes, “What does that mean?” and the salesperson is like, “Well, I don’t know. They just said they need this.” So you want to train people to be able to actually go deep, understand what the problem is.

But then just tell the customer. I don’t have an answer for this.

Then typically what happens organically is that as you do more sales, more and more random things will come up that you will have to go back and ask somebody and eventually you will become an expert hopefully.

Also it’s always a good idea if you can to have your salespeople use a product.

If they can’t use the product, it’s a really, really good idea to actually visit customers. Once in a while actually have your salespeople go and sit next to a customer. Not look at the metrics. All our customers clicked this button. No, actually sit next to a customer and see what do they click. How do they look like? What is the office looking like? What other software do they have? Why are they writing so many notes when they use our software?

Just get that feeling for truly understanding the customer is really important.

What's the best advice for rapidly growing sales teams?

Eric: Yes. [Participant raises a question]

Eric: Biggest piece of advice for a rapidly growing sales team.

Steli: Yes, really rapidly. Just for rapidly growing sales teams, my advice is usually – but for really rapidly growing sales, it’s very different. I don’t know if I have a good answer for this. I mean I could pull something out of my ass but I don’t know if I have a piece of advice for everybody other than get comfortable with fucking things breaking. Always, constantly, shit being bad. There are different degrees of that.

There’s bad because there’s the real world and there’s bad because people lie to you or people don’t keep their promises, not because they don’t want to but because they’re assholes. There’s a difference, right?

There’s a bucket of like I don’t want to work here anymore because people are lying, are not transparent, are doing things that I don’t feel comfortable with. I’m not aligned anymore with and there’s like real world problems. We’re running out of money. The product breaks, whatever. The customers hate us. The competitors just came in. All that shit, they’re like doomsday. We’re almost done tomorrow I’m sure.

You just need to get comfortable with that and as you grow, you always think that – oh, once we’re 100 people, it’s going to be amazing. Oh, once we raise $100 million, everything is going to be amazing.

Nothing will ever be amazing. It’s always going to be painful until it’s not anymore and that usually happens really, really late.

So just get comfortable with messiness because it’s going to be part of your day to day.

How do you stay sharp while taking care of day to day business?

Eric: A couple more questions, yes.

[Participant raises a question]

Steli: Shut up Josh. He worked for me at ElasticSales, so that’s why I’m giving him shit.

[Participant raises a question]

Eric: I’m repeating the question just for the other side of the room and for our video. What drills do you do to stay sharp and stay up-to-date every day for the team and for you?

Steli: Me personally. That’s a good question. So a couple of things. Coming to events like this, having to answer questions is one way. Sales office hours a lot of times is a great way to just learn from other people as well. It’s not just me giving advice. Best way to learn is to teach. So I like to teach a lot. That’s one way.

I do read a lot of sales stuff and most of it really sucks. So I start reading a lot of sales things. I usually don’t end reading those books. But I read books from like insurance salespeople or car salesmen. All the – anything that you could ever imagine. The weirdest things are I watch like scientology videos because I think it’s interesting how they pitch religion versus – I will watch something else. I don’t really care what people are selling. I will watch it. Politicians, PR, like whatever it is. I will watch with the lens of like, “Ha! How are they doing things?”

So I constantly try to read things.

I constantly try to teach and then I still – like a lot of things that I do today in terms of teaching is we do a lot of blog posts, but I started doing a lot of videos, like five, ten-minute videos of me teaching a tactic or something.

Then I will watch that video and just going to fucking hate everything I did there and how I speak and what I say and everything about it sucks. It’s kind of a good way to keep myself sharp and humble. Like oh my god, look at how shitty I presented this idea.

Subject lines that get emails opened

Eric: We will take one last question. Steli, you can pick the final question.

[Participant raises a question]

Eric: What are the best email subject headers that get the best open rates, action rates?

Steli: I assume for outbound emails. Yeah. So a couple of best practices. The number one thing you want to do is don’t make it sound like a marketing email. Don’t make it sound like anything that was written to many people. It needs to sound like something you would write to me as a human being.

So a couple of hacks is don’t capitalize anything.

Maybe you want to misspell something.

It gets open rates up. It’s weird but everything that makes you seem more human will make humans respond more.

So using people’s names tends to work. It’s a little overused.

Everything that works is going to be overused eventually. So you have to keep like reinventing what you do.

But using people’s names, asking a question, usually is a good best practice.

Keeping things really short.

You could do things like “Close” in the subject line. I will open it.

That doesn’t mean I’m going to fucking read your email, but I’m going to open it. It says “Close”. You also have to be like careful. You can do things in emails that will make the open rate go up through the roof. But then will make the response rates go down through the roof, because you just pissed off somebody.

So one of the most effective things that I’ve seen in the past was somebody writing – the subject line started, “Really disappointed …” If you’re a CEO or a founder or anything, out of a million emails – I had a ton of emails. I zoomed in right into “disappointed”. It’s a really strong keyword. I just opened that. What did we fuck up here? Then it continued, “That we weren’t able to connect yet. We’ve sent you three emails.” I was like goddamn you! So that got me like, probs, you got me to open this. Delete. Fuck you.

So just because – so you need – it’s good to have like a balance between what you promise in the subject line and what you deliver in the actual text. So “Close” is not a great promise, but it’s also not like, “I’ve been disappointed with you,” or like whatever your – whatever you could do. Some people – whatever. That’s a different story.

So human, very, very human. “A hundred ways how the news can help your business.” It’s not a good subject line, right? It sounds like a marketing email, PR email. But “quick question about your recruiting?” and that’s also overused. But again, with a question mark at the end, it sounds more like a human being sending me an email or “hiring?” question mark would be a good one for you or, “Does your culture suck, Steli?” The content and the context of what you do deliver on the promise of the subject line.

But you get me intrigued enough to say, “I want to know more,” and then the important thing is once I open it, every sentence needs to be a pitch to why I should read the next sentence. Like people forget that. They put things at the end of the email. I’m never going to get there, so yeah.

Eric: Great. Well, listen, thanks so much for spending the time with us and answering these questions. I really appreciate your time and thanks for coming out to the event tonight.

Steli: Thanks for having me guys.