How to Close the Enterprise When You're Just a Startup


How to Close the Enterprise When You’re Just a Startup (Summit Replay)

close enterprise summit replay image


This video training was originally presented at the 2019 Sales Hacker Success Summit. In it, Co-Founder and CRO of Kronologic, Aaron Bollinger, shows us how to close enterprise level deals when you’re a startup.

What You’ll Learn

  • How to overcome no brand in market
  • How to overcome limited sales support
  • How to overcome limited examples
  • How to overcome no defined budget
  • How to overcome no credible timing event

The Video

Download Aaron’s Checklist for Closing Enterprise Deals Here

Outline, Timestamps, and Transcript

Introduction (00:00)

How to overcome no brand in market (01:23)

Build relationships (01:46)

Expose the buyer’s FOMO (03:13)

Put your money where your mouth is (04:54)

How to overcome limited sales support (06:15)

Enlist the co-founders (06:34)

Leverage the prospect’s buying process (08:04)

The pipeline cures all ills (09:24)

How to overcome limited examples (10:10)

Find innovators (10:36)

Map the status quo (11:30)

Invite them to experiment with you (13:28)

How to overcome no defined budget (14:42)

Map the money (14:58)

Sketch the hero’s journey (17:16)

How to overcome no credible timing event (18:32)

Give credit to the competition (19:01)

Give the gift of white gloves (20:25)

Be Tenacious (21:48)

Be Confident (22:41)

Business starts with “busi” (23:00)

3% (24:26)

You’re the expert (25:38)

Introduction (00:00)

All right guys, welcome to the Sales Hacker’s Success Summit presentation, How To Close The Enterprise When You Are Just A Startup. This is all about those David and Goliath situations we all face early on in our business.

My name’s Aaron Bollinger, I’m co-founder and CRO of Kronologic. Check us out at

I’m going to start the presentation today with a little disclaimer. Sorry, but closing deals from a big company is just not that hard. If you think it’s hard to work at one of the world’s largest companies and close business, then you have not sold from a startup.

Try closing one of the world’s largest businesses as a client, when you yourself have no brand in market, limited sales support, no exact case studies that match the verticals — everybody’s kind of trying it for the first time, so to speak, at least with respect to their business — little to no defined budget for your category, and sometimes no credible timing event.

What I’m going to do today is look at each of these challenges — and those of you out there watching this that have sold or are selling from startups, you know how tough these challenges are to overcome. I want to talk about each one and how I’ve seen myself and others overcome these challenges in their sales career.

How to overcome no brand in market (01:23)

First and foremost, overcoming no brand in market. This is tough. This is me coming to an executive or a buyer and I’m saying,

Trust me. I can’t take you to some big fancy office. I can’t show you commercials. I can’t show you hundreds of clients. I need you to believe in what I’m showing you and I need you to trust me.

Build relationships (01:46)

First strategy here is to build the relationship on a human level, and I think one element of that is you’ve got to get in person. If you want to extract significant budget from companies when you yourself are a small business, it is inefficient to try to do that over digital means.

If I’m going to trust a piece of my career, risk a piece of my reputation within my company by making a bet on something, I’ve got to be able to look somebody in the eyes and have that level of comfort.

It doesn’t always have to be in person, but at the very least you’ve got to utilize video and you’ve got to utilize personal charisma and you’ve got to build trust with that person.

You know, early on, a lot of times that means if we can relate on a personal level, if we can just spend time outside of the office or at least outside of the sales cycle, I will look for every opportunity to do that.

I regularly host happy hours here in town, and I just put a placeholder in the calendar and I say this is a happy hour’s going to happen, and I manifest that happy hour and I make sure that anybody that is open to it shows up so we have the chance to build a personal relationship. Because, that’s going to count. When that person goes to their colleagues and says, “I want to buy this,” and they say, “Buy from who? I’ve never heard of them.” They’ve got to go, “I have, and I’m telling you, trust me, I trust them. This is a relationship worth investing in.

Expose the buyer’s FOMO (03:13)

Second tip here on overcoming know brand in market, expose the buyer’s FOMO. You have no brand in market, but it’s not that exciting to buy the same thing that everybody else in the world has bought. Right?

Identify who your innovators are, seek out those innovators. How do you do that? Go on LinkedIn, take a look at their profile. Have they done something unique before? Have they created something new before? Have they ever created a new program, created a new event themselves, and how do they talk about what they care about?

Somebody that has a passion for innovation — somebody that is upwardly mobile within their career — they are looking for something new, something great, a way to stick out. Right? You offer that.

As a company that is just coming up, not everybody knows about you. You are the DJ or the musician that’s great before everybody else knows about it. And everybody wants to be, at least many people want to be, the first person to know about that great new artist before everybody else in the world does and it’s old news.

Fear of missing out, expose their FOMO, and talk to them about case studies. Say,

If we did something together, I believe this would be the first of its kind in your industry, and it would make sense if we’re proven successful that we should do a case study together. We should probably do an interview together. Is that something you would be open to?

I’ll position it like that. And if we’re talking to the right profile of person, they’re very interested in doing that interview and doing that case study.

Put your money where your mouth is (04:54)

Then, finally, put your money where your mouth is. Right? If you are trying to overcome no brand and market, you can’t ask somebody for a three year contract.

Or, if you do ask for a three year contract, have some terms in there that show that you’re going to prove ROI. You believe in what you’re doing, you know it’s going to work, and when the going gets tough, you are going to do what it takes and overcome those challenges and deliver value to that person. You’re going to offer terms that are reasonable enough that you’re showing them, I will commit to showing you value. I’m not asking you to commit to something that then I can not deliver on.

Relationship starts with the conversation, but it’s still just starting when you sign that contract, and really it goes on throughout showing value, delivering value, and then even marketing that value.

Put your money where your mouth is when you’re trying to overcome no brand in market. It’s helpful early on.

Down the road, you can say, “I demand a two year contract. I demand payment upfront. I demand, you know, a high level of commitment. Why? Because I’ve got the experience and the success and the success cases and references to back it up and you can trust me.

How to overcome limited sales support (06:15)

Second big challenge, overcoming limited sales support. This is tough when you’re a part of a startup, it’s unreasonable to expect that there is a big team around you.

If you’ve sold from a large company before, you know that there is oftentimes a large team around you.

Enlist the co-founders (06:34)

When you’re selling from the startup to the enterprise, the first thing to do is enlist your co-founders, you know? Somebody may have a title, they may have a CTO, CEO, co-founder, or whatever. But whatever that person’s title is, enlist them in the sales process. Look for, what are they good at? Could somebody come in and help with a technical conversation? Could somebody just serve as an additional viewpoint that buys you time within a sales cycle to answer a really tough question, right?

If there’s just one brain — and this is important too, which is just the meeting dynamics. You don’t want one on five. Like, that is really hard. And, of course, it’s unreasonable for you to be five of you on one. Right?

You want to keep a reasonable ratio of seller and prospect. So, if they’ve got two or three people, if they’re a big opportunity for at least the first, you know, 10 clients you win, bring in the cofounders so that you’ve got at least a two on two, or at worst maybe a two on three, two on four, but you don’t want to be one on four, one on five. Even if you’re the best salesperson in the world, it’s really hard to win that deal.

The goal here is not to be a hero. The goal here is to win the deal and grow the business.

Leverage the prospect’s buying process (08:04)

Second strategy, leverage the prospect’s buying process. I see this all the time. You know, early on in a business you may have a prospect that says,

Okay, can you send your MSA?

Can you send your agreement?

Can you send all of your terms and conditions?

Can you advise or propose what step I need to do next?

As your company grows, you will have best practices and you will be able to prescribe all of those things. But, early on it’s unreasonable to expect that your five person team, 10 person team, 20 person team has the same level of rigor and strategy built into your selling process as your buyers do in enterprise with their buying process, so leverage that.

I often say, “Well, how about this, can you send us your MSA? Do you guys have a pre-approved set of terms that you know you can buy from? Well, send me that.

Then, if there’s something that I have to have that’s not in there, I’ll add it in. If there’s something that I can’t live with, I’ll remove it. But, let’s start with what you have that’s been kind of tried and tested over years and thousands of folks, versus what we’re kind of building up from nothing.

The pipeline cures all ills (09:24)

Third strategy, pipeline cures all ills. You know you don’t have the ultimate sales machine early on, so, make sure you have a lot of conversations. You’re maintaining a funnel shape that looks like this [Gestures his hands in a funnel shape].

If it looks like this [Gestures his hands straight up and down], that’s a problem. If it looks like this [Gestures his hands flat], that’s a problem. Always keep it in this shape [Gestures his hands in a funnel shape].

Look at the stages in your pipeline, it should always be like in this shape. If it’s in this shape, you should have enough in the top that enough will fall through the bottom at the end of the day to give you what you need, even when you don’t have the ultimate sales machine to get through technical diligence and business case and contract negotiations as fast as absolutely possible.

RELATED: Improve Your Pipeline: Let Sales Control the Flow of MQLs (Why It Matters and How to Do It)

How to overcome limited examples (10:10)

Third big challenge, limited examples. I’m asking you to pay to use our technology for your 200 person client success work. But, I have no examples of our technology used in the client success team or by a client success leader.

That’s hard to do.

Find innovators (10:36)

Again, I go to find your innovators. And specifically — however I get into an account, whether that is through a friend, someone in a network, or somebody I meet at an event — one of the first things I’ll ask them is,

Okay, it sounds like you have some interest in what we’re doing, or at least you’re impressed with how we’re approaching this problem. Do you have a sales ops leader or do you have a client success leader on the team that is an innovator? You know, somebody that creates new new ideas, somebody that champions new ideas, somebody that gets things done and isn’t just following the playbook.

I ask them that. That’s who I want to talk to. And if you don’t have that one, just tell me. Maybe we come back and we finish up this conversation later on, but right now I have limited time. I need to be primarily speaking with innovators. That’s first and foremost.

Map the status quo (11:30)

Second one is, you know, if they have fear — as everybody does, at least a modest amount of fear, a reasonable amount of fear around doing something new that you don’t have any examples of — make a map for them and detail the existing status quo. What are you doing today?

So what I’m proposing sounds new, okay, and admittedly it’s a little scary. Let’s just take a step back for a minute, and let’s talk about exactly what you guys are doing today. Then, try to get a couple challenging questions in there.

If they say, “We start with this and then we do this, and then that ends up doing this.”

Then try to get like, “Okay, now why did you go directly from that to this, and how is that working for you?

A lot of times people say, “Oh, it works fine. This is how we do it.

Okay, have you quantified your success and how successful you are in that current framework?

Well, no. I mean this is how we’ve done it for a long time,” and blah, blah blah.

You may have to have a framework. I know at Kronologic we’ve created something we called meeting math. It’s kind of like a subset of sales math. And we talk about two metrics, average value per meeting — what is your average value per meeting? — then, what is your lead deficit?

Once we have average value per meeting, we have to calculate lead deficit, which is basically the TAM of any company’s leads that aren’t being converted to opportunities.

If you’ve got to map the status quo and people don’t understand at like a conceptual level what’s missing from their current status quo, then it’s up to you to create that map, or that framework, a calculator, whatever it is to help them quantify what is suboptimal about their existing status quo. I encourage you to do that, and that also is a great way to become a thought leader.

Invite them to experiment with you (13:28)

Then, the final thing I would say about how to overcome limited examples is invite your prospect to experiment with you. This is, you know, like anything in life, be flawsome. Right? Know what your flaws are and still be awesome.

If you know that this is an experiment, and nobody’s done this before or nobody’s done it just like this before, then just admit that and say,

Hey, there is no getting around the fact that you’re going to be one of the first people in this industry to use this exact technology. But, you seem like the kind of person who does make smart wagers for the opportunity to show significant success and all of the career advancement and earnings and everything else, acclaim that goes with that. I believe that you and I, if you’re open to it, should experiment together on something new. Let’s see how much success we can have, and we can start small, but count on me to partner with you to really innovate and create something great and new.

How to overcome no defined budget (14:42)

Okay, fourth big challenge, overcoming no defined budget for your category.

This is really cool, but all our budget’s tied up.”

“This is really neat, but it’s not something we can spend money on right now.

Map the money (14:58)

First and foremost, how do you address this? Map the money today. Where is the money that goes to this problem, or a related problem, today?

You’re going to have to be really sharp about this. You’re going to have to understand the context of their space to get a question in and do it with credibility.

But, for Kronologic specifically, I’ll just speak to this. What I talk about is,

“If you didn’t use us to book meetings from leads, how would you approach this? Well, you would approach this by hiring more SDRs. You would approach it by hiring more people. Right? Well, right. Okay, so what does that cost you today? Typical SDR across the industry costs about $7,000 when you look at wages and comp and benefits. They book about 35 meetings a month — qualified opportunities on average — for an average value of about $200 per meeting.”

If you want to outsource it to companies, I can tell you what that cost per meeting is. I’m helping them map where their dollars are actually going today.

When people hear that, and then they hear the Kronologic costs a fraction of that per meeting that we book for you, they go, “Huh.” And it gives them the context and the foundation they need to really evaluate how efficient their current dollars are today.

“And guess what? Maybe you don’t — you’re not going to fire your SDR team — I wouldn’t encourage you to do that, but maybe you promote 5% of it into AEs and you let Kronologic book out more meetings for you at a fraction of the price. So, you’ve got more meetings to close and less money going out the door just to help you get those meetings in the first place.”

Okay, map the money today. Right? Then, get your math on. Have an ROI framework, and if you put up a big spreadsheet in front of me, I’m probably going to lose interest quick. Have math that is distilled down to a framework that allows you to communicate something at the speed of business.

This can be no more than a few, a handful of facts and figures, no more than a handful of equations. But help people understand, “I roughly cost this and I roughly can be estimated to help produce you this.” Right? If you don’t have that, it’s going to take you forever to get budget.

Sketch the hero’s journey (17:16)

Then finally, you know, sketch the hero’s journey. Help them understand what success looks like. Help them envision that journey for them.

“Look, today you’ve got to go, and I know it’s going to be hard for you to get budget for this because we’re not that well known. However, if the numbers we’ve walked through today are correct, even if they’re close to correct, we’ve agreed already that the ROI on that is 10X. And you’re going to have an extra half a million dollars or more in bookings in the next quarter alone or the next year alone to show that impact.”

When you do that, there is no doubt that that is going to help you crush your quota. It’s going to help you advance your company overall, and it’s not going to be missed by your executive team that you took the initiative to take a risk, take a smart, sensible gamble that ultimately helped move the business in the right direction, right?

Sketch that hero’s journey for them.

How to overcome no credible timing event (18:32)

Then, one of the final big challenge to overcome here is overcoming a no credible timing event. This one is really tough. Early days, I’ve heard it at every place I’ve ever sold. I always get some reactions that say,

Aaron, this is great. I’m really interested. However, I can’t do anything on this until next year. This is great. I just don’t know when this is going to be a priority for us.

Give credit to the competition (19:01)

Right? A couple things to do here, and there’s no getting around the fact that this is challenging, but one of those is give some credit to their competition. If anybody in their competitive space is taking a look at you, talk about that.

I have absolutely created opportunities in one business that began with an email that said two of your competitors are evaluating us. Your biggest competitor right now is… you know… I met with your biggest competitor onsite last month… these kinds of things.

Now, you don’t want to do this if you don’t have it. But, if you realize that the timing event is going to be the roadblock here, talk about their competition and the fact that their competition is going to potentially move forward with this soon.

If the competition moves forward with this in a month — and they’re going to begin to see all of that success and value — at the very least, you’re helping just create a little bit of tension there that’s going to help you create some level of urgency and a little bit more interest.

And the idea that I don’t have a year to think about this because my competition gets too it first, and it really works as well as this salesperson is confident it will, man, I’m going to look bad. And then I got to go back to this person in six months, or in three months, and their pricing may be higher.


Give the gift of white gloves (20:25)

Okay, and then give the gift of the white gloves. This is actually a hidden objection underneath a lot of objections. Which is, I don’t want to do more work right now. Like,

I’m happy, I’m getting my salary, I’m getting my bonus, I’m well-respected, and I’m able to go 能提现的真人游戏平台home at night and spend time with my family. And ultimately, like, I’m worried this is just something else that’s going to create additional headache and work for me. And even if the risk is pretty good, I mean, the reward potentially is pretty good, I don’t want to risk the additional work. It’s too much.

Well, talk about the white glove approach. Talk about the fact that if they work with you, you are going to go to work [for them]. And I use the phrase a lot, “Put me to work. We will deliver and we will continue to work and continue to improve and we will do everything we can.

Early on, when you’re selling from a startup, you’ve got to commit to this. You don’t have the luxury of a large company to say, “I‘ll get to it when I get to it.” You’ve got to say,

I’m going to go do everything right now, to basically show you results with as little disruption to your day. I have an appreciation for how busy you are and I’m going to commit to doing everything I can to show you value without causing you trouble.”

Be Tenacious (21:48)

Then finally, just tenacity. Right? Just be tenacious.

If I just see somebody continually, they’re on top of it, they’re always on follow ups. When they say they show up, they show up early. When any event happens in the news, any new updates that happen that might affect my opinion of them, they’re always on top of it. They’re always reaching out to me. I realize, man, you know, if I do work with these guys, if the rest of this company exhibits the same level of tenacity as the sales team, they’re going to take good care of me.

There’s no way they’re going to keep this level of tenacity on the sales side, or at least not often. Companies that don’t perform as well, their sales teams are much more kind of transactional and much more passive.

Stay tenacious.

Be Confident (22:41)

Excellent, well finally, just a few last words on reasons for confidence. Okay? There’s a lot of challenges ahead of you when you’re trying to sell to the enterprise from a small business, from a startup — and I’ve got sympathy and empathy — and I’ve got reasons I want to share for confidence.

Business starts with “busi” (23:00)

First one is, business starts with “busi”. Just get out there. It really does. Like, you don’t know what you don’t know until you just go out there and have real world experiences that start to expose opportunities to you.

I told you one of the things I do is I just say, “Okay, Thursday night, this bar, we’re doing a happy hour.” I’m going to go reach out to 15 people within my network, and just ask them for their advice. “Can I just have 15 minutes with you to tell you what I’m doing and ask you what you think I should know about, what you like, what you don’t like.

If you just get busy and get out there and put energy into systems, that is going to expose opportunities. And worst case scenario, you hear the same issues so many times that you can credibly go, “Hey, at this point, I know something is not working, so I’ve got to pivot or we’ve got to change something about what we do,

But don’t be scared to just get out there and take as many meetings as possible early on until you have a lot of data points. Sitting around inside an office or a house or at a happy hour and just simply, you know, discussing things internally is not a great strategy.

You’ve got to go get more and more and more external data points.

3% (24:26)

Another reason for confidence is 3%. 3% is — you know, on average across the industries at any given time — it’s the percentage of your market that’s actually interested in what you have to offer.

If you have 10 meetings, right, on average, you’re not going to touch that 3%. If you have 10 meetings and 10 people go, “This is interesting, but I can’t buy right now,” that is completely possible, and actually, it’s probable. If 10 people in a row say, “I don’t like this,” then you got an issue. But, if 10 prospects in a row say, “I am interested, but not right now,” that’s right.

Now, if you get to 30, so if you take 3% times 33 where we get it up to 10. If you do 33 prospects and one of them doesn’t say, “This is great and I want to buy it now,” then you’ve got some other issues.

But, just know, 3%, and again, maintain that pipeline shape. You get a lot of stuff up there, and then every quarter, every month, a few of them will follow through. Remember that 3% when you hear over and over again, “I think this is great. I can’t buy right now.

RELATED: The Definitive Guide to Lead Generation: 6-Steps to a Winning Lead-Gen Process

You’re the expert (25:38)

Okay, and then finally, you are the expert, or you’re about to be the expert. If you put your heart and soul and your focus into a topic and you continue to just chip away at that topic week after week, month after month, you will become the expert.

You will have been thinking about this more than anybody else. Just by sheer might and focus, you will become the expert. Early on, you’re going in there saying, “I think this is great. Do you also?” At some point, you’re going to be able to say,

I’ve been thinking about this so much. Let me walk you through how this can be relevant for you. I understand many of the things that you’re likely thinking about, and I have thought about them for a long time and I can look you in the eyes and say this is for at least these use cases and these scenarios, this is a no brainer decision and you should move forward.

Three reasons for confidence there, and I encourage all of you to keep fighting on. I think it’s a noble endeavor to bring new ideas into this world. Not simply, you know, be out there kind of hocking ideas that everybody already agrees with.

I encourage you to keep selling to the enterprise from the startup.

Again, I am a cofounder at Kronologic, we are a calendar monetization engine. We have some really cool, amazing things going on. You can find us at That’s Kronologic with a K.

I’m, and you can use our technology for yourself in a single click on our website, and a big fan of Sales Hacker and super excited to present for you today. Until next time, onward and upward.


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