What I Consider Important in 'Enterprise Sales' After 20 Years of Experience

I have been dedicated to corporate sales for 20 years.

After graduating from Keio University, I joined NTT Communications. Since then, I have worked at LINE and Mercari, and I am now striving in enterprise sales at a startup called Growth X.

In fact, when I was young, I thought, 'I absolutely do not want to do sales.' I had an image of it being about being glib and manipulative. Yet, before I knew it, I became immersed in sales, and 20 years have passed in the blink of an eye.

Life is a mysterious thing.

In this note, I will share what I have realized through my many years of experience regarding 'what I believe is important in enterprise sales.'

The structure consists of

Part 1: Understanding People
Part 2: Understanding Organizations
Part 3: Understanding That It Takes Time

these three parts.

Although it ended up being over 10,000 characters in total, I hope it serves as a hint for those struggling with enterprise sales.

Part 1: Understanding People

What if the customer in front of you suddenly starts getting angry?

This happened when I proposed a large-scale project to a major corporation.

When I smoothly presented a document with the list price, the customer in front of me suddenly started getting angry.

'We are saying we want to work together, so what is the meaning of suddenly showing us a list price!'

Now, when this happens, what would you think? You might think it is unreasonable. After all, they suddenly started getting angry just because I showed them the price. In fact, the junior colleague who accompanied me even started to cry.

But what I thought was'This customer is serious.'that was it.

The 'serious' here does not refer to the 'anger.' The anger is a lie. The anger is a lie, a performance. On the other hand, the 'desire to move the project forward' is what is serious.

If they weren't serious, they wouldn't have said anything at all. They would likely be smiling and saying things like, 'We will consider it.' Because they were seriously trying to partner with us, they tested us by coming on strong once to see if we could keep up.

I thought,'I see, this is just a bluff, so it's actually an opportunity.'and calmly continued the conversation. Then, the customer also adopted an attitude of 'You get it, don't you,' and a relationship of trust was born.

Ultimately, this large-scale project was successfully contracted.

Why would they do such a thing?

By that time, I already had plenty of sales experience, so I was used to those kinds of situations. If I had been a young employee, I might have been outraged, thinking, 'What a rude person.'

What is important in sales is not to react emotionally. It is to think, 'Why is this person doing this?'

Once you are able to view what is happening in front of you from a meta-perspective, even if you are scolded, you might start to think, 'Perhaps they are actually trying to build a deeper relationship of trust.'

Human beings are deep, complex creatures who are not one-dimensional. There is often a 'true intention' behind their words that they want to convey. I enjoy discovering that multifaceted nature of people.

Enterprise sales is a journey to explore the true feelings and intentions of people.

Once I was able to think that way, sales suddenly became fun. I don't think many people like cold calling, but when you can look at it from this meta-perspective, it starts to become enjoyable.

Apology visits also stopped being painful.

I found myself looking down on apology visits and enjoying them to some extent. Of course, while reflecting on the situation, I started to verify how the customer's reaction changes depending on the angle of my bow when apologizing, or what kind of reaction the customer shows when I nod at certain points.

'Hey Sugi-chan, did you spray your head with a misting bottle?'

There is an event that triggered me to acquire that 'meta-perspective'.

It happened when I went on an apology visit with my section manager. I was still in my 20s.

Back then, apology visits were a heavy burden. We had to apologize even though it wasn't our fault. I felt depressed and resentful.

In the midst of that, the manager said, 'Hey Sugi-chan, did you spray your head with a misting bottle?' In other words, he suggested that to show how deeply we are bowing, maybe I should spray some mist to make it look like I'm sweating.

He probably wasn't saying it seriously. I didn't actually spray any mist. But watching my boss enjoy himself while telling jokes like that, I thought, 'He's amazing.' Through experiences like that, I gradually became able to enjoy any situation.

It was also that manager who said, 'Can you report to me after you've been turned down three times?'

I was originally shy, so I wasn't good at inviting customers out for drinks. Even when I said, 'Would you like to go for a drink sometime?', they would say things like, 'It might be too early for that.'

When I told my manager, 'I was turned down,' he said, 'Sugi-chan, a drinking invitation is something that starts after you get turned down. Can you report to me after you've been turned down three times?'

The real challenge starts after being turned down, and that's the same in sales. From then on, being turned down became like a 'greeting,' and I stopped thinking anything of it.

The essence of humanity revealed through corporate sales

What I think after many years of corporate sales is that humans may seem rational, but they are irrational after all. I believe that is just how humans are.

Corporate purchases are also made through 'irrational decisions'.

It is often thought that corporations make purchases based on logic and sound rational judgment, but the reality is not so. The reality is that 'even the objectives are irrational.' Even though the objectives are irrational, they are framed to look rational.

Let me tell you about a certain competition.

In a competition, the client first sends out something like a request for proposal, saying, 'We want to do this, so we are looking for this kind of tool.' On the surface, it is set up so that 'each company submits the same content in writing on the same day.' The general flow is that they then make a rational judgment based on selection criteria and ultimately choose Company A.

However, in reality, there is already complete 'irrationality' here as well.

For example, the information provided to each company is not always uniform. Even if the documents are the same, they might meet face-to-face with the person they want to win to give them hints. Especially when products are similar, the outcome is often already decided at that point. That happens quite often.

'Mr. Sugimoto, your company is ten lengths behind.'

There were three companies in that competition, and the client told me, 'Mr. Sugimoto, I'm sorry, but I don't think we can hire your company.'

However, I judged that 'saying you "think" you can't doesn't mean it's decided that you can't.' So, I went to ask about the internal situation.

Once we were one-on-one in a private room, the client started to talk.

'Mr. Sugimoto, it's impossible now. The current situation is that Horse A is about to reach the finish line. Horse B is three lengths behind that, and your company is ten lengths behind. That is the gap we are looking at.'

The client was a fan of horse racing. That is why they used that expression. At that moment, I intuitively understood that 'one length' meant 1 million yen. In other words, there was likely a 10 million yen monthly difference between the leader and us.

I said, 'By the way, would it be alright if I reviewed the price and sent it again in two or three days?' The client's reply was, 'I think it's difficult, but well, you are free to send it.'

There was various back-and-forth after that, but in the end, we managed to overcome the 10 million yen monthly gap and were awarded an order worth about 700 million yen.

The rationality of 'wanting to choose someone you can trust'

At the time, I often went horse racing with that client on my days off to have them teach me. I think the relationship built during those times also played a part.

From the client's perspective, while they 'want to let someone win,' they cannot explicitly say so. They also cannot show exactly 'how much of a gap there is.' That is why I think they gave me a hint using the expression of 'lengths.'

Writing it like this makes it look like an irrational decision, but I think there is also a rational aspect to it. That is the rationality of 'choosing a partner you can trust.'

Especially in the case of long-term projects, it is only natural for a client to choose a partner they can trust. When that happens, the feeling of 'is there anything I can do to help the person I trust win?' naturally arises.

In enterprise sales, the part where you build that kind of relationship is truly important. It's not as if things will turn around just by being rational and logical. After all, humans are irrational creatures. Perhaps 'becoming friends' is also an irrational concept. However, in the end,the feeling that 'I want to work with people I can trust' becomes important.

Of course, the rationality of 'being able to solve the customer's problems' must be the foundation. That goes without saying. Without that rationality, irrationality will never win.

However, ultimately,you need value added on top of that rational base, and that is where relationships, trust, and feelings that might seem irrational come into play.

Can you meet without an agenda?

'People at large companies are rigid, so they are hard to deal with.'

Some people might think that. But if you reject them because of that, nothing will move forward.Even if it's a large company, it's driven by individual human beings.If you interact with people properly, various things will come into view.

As I built relationships with all kinds of people, I also met people who were rigid. There were people who were obedient to the organization and inflexible. But even with such people, if you visit them many times and gradually become friends,and come to understand their birthdays, family structure, and values, you start to see many different sides of them.

There was a serious and seemingly stubborn person at one company.

But as I met him several times, I heard him say, 'My 3-year-old daughter says she wants to ski, so we are going skiing for the New Year holidays.' At times like that, you catch a glimpse of a different side of them, thinking, 'He says strict things usually, but he probably has a soft spot for his daughter.'

I happened to have a desk calendar with a character on it. It was a company novelty, but I handed it to him, saying, 'Do you think your daughter would be happy with this?' He replied, 'Oh, I don't know if she'll be happy, but I'll try giving it to her. I have to be careful because she licks everything, though.'

It's not that I used that as a tool. I just had a casual conversation, but as I was leaving, he said,'Mr. Sugimoto, you should come back again around the second week of the new year.'When I actually went after the new year, it turned out to be advance information about an important competition. If you interact with people thinking, 'Humans are interesting,' such information sometimes just pops up.

The best thing isto be able to go see them without a purpose.

If you have a relationship with an agenda, you can't really go beyond that. It's best if you can meet in a state where there is nothing, like 'Can I come over to hang out?' or 'Why don't we just meet and talk?'

If you can have a relationship where you can chat about nothing or just go out for a drink, work will eventually go well too. In enterprise sales, 'having a relationship where you can have useless conversations' is extremely important.

Part 2: Understanding the Organization

Humans are social creatures

Humans are irrational beings, and I believe that large corporate organizations, which are collections of such humans, are also irrational.

Even if a decision looks rational, the background can be irrational. For example, when people say, 'Let's decide by majority vote,' in reality, everyone might just want to go along with the crowd. There is also the logic of factions.Rather than 'is that choice really correct,' they think, 'whose opinion should I follow to benefit myself?'that is.

This is a natural consequence.

Humans cannot live alone in the first place. The foundation is being a 'social' creature for whom cooperation is essential.If you are disliked within the society that is a company, your own position is in danger. That is why you follow the opinions of strong people.

That is just how things are.

There was a time when the business integration between Nissan and Honda fell through. Looking at it objectively from the outside, it might have been more rational to integrate. However, humans are generally incapable of being objective. Especially when you are inside a company, the company tends to become 'everything'.

There is the name 'Nissan' and its history. There are people who have been working devotedly for it all this time.'Integrating here would be a denial of everything we have done.' If many people think that way, it is only natural to take those opinions into account.

When doing enterprise sales, it is important to first understand that 'organizations operate based on such dynamics'.

Surprisingly, minorities drive organizations

In terms of the dynamic of 'following the crowd,' it is inevitable that everything tends toward the majority.

But what is interesting is thatnot everyone is like that.

There are minorities within a company. And surprisingly, these minority individuals are often the ones driving internal projects. I sometimes see cases where innovation is born from employees who are on the sidelines, and when you look at the movements of large corporations, that actually happens.

Normally, a company operates on the dynamic of 'following the crowd.' The reason is that each individual is trying to survive there. Or more specifically, they want to get promoted. On the other hand, there are also types of people who resist this. They are people who operate more on 'field-first' or 'customer-first' principles rather than 'organizational logic'.

And when this'majority that followed the crowd and got promoted' and the 'minority that is field-first' come together, things start to move.

What you often see in large companies is a case where someone on the minority side who knows the field best acts as the 'trusted aide' to the executive. The executive's trusted aide is surprisingly not someone on the majority side. Someone who knows the field well and has strong connections to the field is often right next to the executive. Such people drive innovative projects that would 'normally be difficult to take a risk on'.

The executive understands this.

They know that if they keep making conservative and rational choices, they will lose their competitive advantage. They know that sometimes they have to create something bold and innovative. That is why they make good use of people on the minority side, connect with the field, and push forward with innovative projects.

Therefore, in enterprise sales, it often works well to approach people on the minority side who want to do new things. Where things don't go well when following the standard approval process,it can go through smoothly if you are connected to the president or vice president's 'trusted aide' unexpectedly.

There are many cases that have succeeded that way.

How to find the 'people of fire'

I call those people on the minority side 'people of fire'.

To do new things, it is important to find these people of fire.People of fire have a strong passion for their company's products, convey their appeal and value to many people, and coordinate within the company to make them a reality.

Among the people of fire, there are those who are on the fast track to promotion, and there are those who, regardless of promotion, act because they believe 'this must be done' for the company. Both patterns exist. Therefore, you should not dismiss someone just because they are off the promotion track or have a low rank.

So, how do you find such people?

One thing is to 'keep searching diligently.' When I worked at LINE, there was a major project to get Yamato Transport to adopt LINE, and the key to success was reaching the key person.

My boss at the time, Shintaro Tabata, also said,'This is just like a treasure hunt,'and it really is about just keeping on searching and digging. It means approaching various places in a gritty way. At first, that is all you can do.

Another thing is that 'you must keep burning yourself.'People who are on fire naturally attract others who are also burning.When you are burning with a vision, people who are drawn to that vision will eventually want to talk or introduce you, and you will be able to meet them.

That is why I believe salespeople must keep their fire burning. Naturally, you look for 'people on fire,' but if you don't become a 'person on fire' yourself first, others won't be drawn to you.

There are many ways to let people know that you are burning.

I once compiled information that might be useful to clients to pique their interest and sent out an email called'Sugimoto Newsletter.'Then, for one reason or another, they would start reaching out to me.

Speaking at events or holding closed study sessions is also good. You might not make connections immediately, but if you continue diligently, people will eventually reach out to you.

Some people do not come out into the open

When I say 'people on fire,' you might imagine people who stand out, but there are many such people who do not come out into the open. It is easy to identify people who have articles written about them publicly, but there are many people on fire within large corporations who do not appear in public.

And,some truly interesting people do not even use X.Therefore, you cannot just follow people who stand out on social media and frequently speak at events.

What is important is to find not just 'interesting people,' but 'people who can execute.'There is a wide river flowing between people who want to do interesting things and people who can execute them.People who say 'I want to do something interesting!' are different from those who can actually make it happen within a company. Unless both are combined, a project will not succeed.

I think about 5% of people in large corporations are 'people on fire.'

If 10 out of 100 people want to do something interesting, only about half of them can actually execute it. There are many people who just say things like 'Let's do something interesting sometime' and are just being agreeable. But I don't think that leads to a successful project.

After meeting many people over many years, I think thatyou should not have too many expectations.Because if you have expectations, you will end up disappointed. In enterprise sales, it is just right to 'go in without expectations.' If you interact with various people without expectations, good opportunities will sometimes come your way unexpectedly.

The 'game of telephone' that happens in large corporations

Even if you meet a person on fire and discussions begin, in the case of enterprise sales, you must also consider the client's 'internal' circumstances.

There are many stakeholders in an enterprise.

Even regarding a single document,what a frontline staff member thinks is 'good' is different from what management thinks is 'good.'A 'game of telephone' always happens within an enterprise. Documents take on a life of their own. Therefore, you must create documents that can withstand this game of telephone.

A company hasa 'vertical' mesh of departments and a 'horizontal' mesh of job titles.The messages that should be conveyed to frontline employees, middle management business leaders, and executives are all different. Each person has different intentions. They have different missions they are responsible for. They are evaluated on different criteria. Therefore, you must communicate in a way that corresponds to each of them.

Naturally, enterprise sales will not go well if you just hand over documents. When handing over documents, you should teach them how to convey the information, saying,'Please explain it to your boss like this.'Or, you can say, 'I will be visiting your company, so let's explain it together,' and create an opportunity for a presentation.

Holding study sessions and inviting people from each department is also effective.

Observe who is positive and who is negative there. For negative people, engage in communication that brings their negativity back to zero, and for positive people, engage in communication that encourages them to be even more forward-looking.

'Conviction' and 'Persuasion'

To move things forward, both 'conviction' and 'persuasion' are necessary.

In enterprise sales, you first get the person in front of you to have 'conviction.' Start by communicating in a way that gains their conviction. However, that alone is not enough. You also need to provide them with the logic to 'persuade' their superiors and decision-makers. is necessary.

For example, suppose you are selling a sales tool.

If you tell the staff on the ground, 'If you use this, your work will become easier,' they will likely have 'conviction.' On the other hand, what happens if the staff on the ground tells their boss, who is the decision-maker, 'Please introduce this because it will make my work easier'? The boss will likely shoot it down, saying, 'That just makes things easier for you.'

In such cases, you persuade them by saying, 'If we introduce this, the team's overall performance will improve, and we can achieve this term's goals.' If the boss's mission is to achieve team goals, they will surely be convinced.

If the executive is the decision-maker, you tell them, 'If you introduce sales DX, efficiency will improve, performance will rise, and it will be reflected in the stock price.' When the message is passed around the company like a game of telephone, providing that 'logic' will help move things forward.

Getting the OK from the decision-maker is not the end

What makes it difficult is that, for example, just because the president is convinced does not mean the decision will be finalized.

Perhaps it is the trend of the times. Today's management values the voices of those on the front lines. Many will ask their subordinates, 'Is it okay to introduce this?' to build consensus. Therefore, a flow emerges from the president's 'conviction' to the reverse 'persuasion' of the employees. This creates a need to teach them, 'Here is the logic to persuade your subordinates.'

This is where people often get it wrong.

People tend to think, 'Since the decision-maker said OK, it will be introduced,' but it doesn't happen. It is common for cases to be stopped by opposition from the front lines. The result changes depending on whether or not you add words like, 'This will make the front lines so much easier,' 'Here are the effects it will have,' or 'Doing this will also make the customers happy' when trying to introduce it to the front lines.

Part 3: Understanding that it takes time

Two years without results

When I was 34, I moved from NTT Communications to LINE.

As an enterprise salesperson, my mission was to have LINE introduced to all kinds of infrastructure companies. However, at the time, I had no connections with infrastructure companies.

In the end, it took about two years before I saw any major results.

My direct supervisor, Mr. Tabata, told me, 'I'll be patient for two years,' but halfway through, he lowered my salary, albeit just a little. I thought, 'Wait, you said you wouldn't lower it!'

Well, that's fine, but... I will never forget January 15, 2016. After two years of working behind the scenes since joining the company, my efforts bore fruit, and our introduction to Yamato Transport was finalized. In the end, the presidents shook hands, and the partnership was decided.

What was I doing during those two years of preparation?

I focused on aiming for the big fish, or rather, infrastructure companies. I didn't have any particular title, and people around me called me the 'Special Mission Manager'.

As for specific actions, I went to events, had people introduce me to others, and went to places where customers gathered...

In any case, I continued to doggedly search for and meet with the 'key people' so that I could get even a little closer to the places I absolutely wanted to target, such as Yamato Transport and ANA.

Timing is more important than the content of the proposal

The content of a proposal is important, but timing is even more critical.

For example, during a business meeting, there might be five people on the client side, and the person sitting at the far end might be the 'key person.' Just because they are at the end doesn't mean you should underestimate them. Even when you think, 'The reaction wasn't that great,' you might receive an email like this from the person who was sitting at the end.

'Thank you for the other day. We have decided to pass on this for now, but I personally think it is very important...'

In such cases, I make it a point to meet with that person regularly. It is true that the timing isn't right yet, but it is common for opportunities to arise when that person's position changes or the winds shift.

Timing speaks louder than the content of the proposal.

A ship will not move just because the wind blows at any given time. You must wait for the wind to start blowing and then spread your sails. This sense is extremely important. Therefore, enterprise sales also requires the 'courage to wait until then.' Unless you are someone who can do that, it is difficult to achieve results.

It is common for there to be a time lag of more than a year.

That is why you should not think, 'Oh, this isn't going to be a deal.'You must not leave a bad impression or stop staying in touch. Someone might change jobs and talk about it there, or someone might get promoted and change positions.

There are many patterns where nothing came of it at the time, but then that person changed jobs, and suddenly it became a business opportunity. When you have been doing enterprise sales for a long time, you realize this strongly.

Why don't I worry about quotas?

During the two years of preparation, the state of 'only God knows whether the results will bear fruit or not' continued. No one guarantees the future. It makes you anxious.

However, in enterprise sales,'continuing to dig holes' is important.

People who struggle to get results keep digging holes in various places and then quit halfway through. That is no good. It takes time for results to appear, and it is rare for them to appear at all. You must first understand that.

The frustrating thing is that if you don't get results in sales, you get pressured. Even if you aren't pressured, it becomes difficult to stay at the company. And before you know it, you start doing other things.

However, in my case, for better or worse, I don't worry about quotas.Even if I'm pressured, I'll say "I'm sorry," but in reality, I'm not worried at all.

The reason I can stay unconcerned is that I am doing this to change society. I'm not trying to sound cool, but I truly believed that "if Yamato Transport introduces LINE, it will become incredibly convenient and society will be better for it. That's why it will definitely succeed." Because of that, my activities never stalled. As a result of not stalling, it succeeded in about two years.

There are many important things in enterprise sales, but this might be the most important one. In other words, passion is more important than skills or know-how.The passion that "I will change society with this" or "I will make society better with this." Without that, you can't keep going, and conversely, I think that if you have that, everything else will work out.

Understanding people, contributing to solving customer problems on the front lines, and being the first to receive the joy of success—that is the fun of enterprise sales.

And you can become a starting point for changing society.

Changing the customer, changing the company, changing the people beyond that, and changing society. I think the potential for that is the appeal of the job of enterprise sales.

Closing is just the "beginning"

What makes enterprise sales different from other products is that in most cases, the relationship after the purchase is longer. It doesn't end with a single transaction. Rather, after closing, it feels like we are building the work together.

That's why it's also important to have them feel, even before closing, that "it seems interesting to work with Sugimoto" or "it seems like things will go well working with Sugimoto."

The case of Yamato Transport didn't end with the introduction of LINE either.

For example, to liven up Yamato Transport's LINE account, we also sold stickers. When I thought together with the person in charge at Yamato, "How can we make Yamato Transport more liked?", the idea came up: "Why don't we make LINE stickers?"

When we finally released them, they became a hit on social media, with people saying things like, "Yamato's stickers are super cute!" Because the stickers went viral, people felt closer to Yamato, and the Yamato account started being used more. By doing that, redeliveries should decrease, and it should also make things easier for the sales drivers.It's a win-win for everyone.

By proposing the stickers, my work increased. I went home later. But I thought, "It would be interesting if this became a trend." Naturally, I didn't get any profit from the stickers. My salary didn't go up either. But I was happy because I felt that society had become even just a little bit better.

Conclusion: I thought I would never want to do sales

As I mentioned at the beginning, I thought I would never want to do sales. That was because I had the impression that it meant selling things with smooth talk. And also, I was originally shy.

On the other hand, I had a fundamental desire to "understand human beings."

Although I was assigned to the sales department against my will, while working behind my boss, I started to think, "Wait? Isn't there no other place where you can see people so clearly?" Especially in large companies, there are multiple decision-makers and stakeholders. The project is swayed by the movements of those people. I started to think that was the difficult part, and also the interesting part.

My personal interest in "wanting to understand human beings" matched the activity of "unraveling the relationships between stakeholders in an organization" in enterprise sales. That might be the reason I have been able to continue this job for 20 years.

"Humans are pathetic, but they are lovable."

This is my tentative answer to understanding human beings.

Many people say they are doing things 'for the company,' but deep down, their true motives are often 'for themselves.' While they might say, 'Company policy is...' or 'Upper management says...', the reality is often a desire for personal advancement, a need to assert dominance, or a craving for recognition and fame. While I might think, 'That's pretty pathetic,' I also find it rather endearing. Naturally, this includes myself as well.

What's interesting is that the opposite also happens.

In other words, there are people who tell those around them, 'I'm doing this for myself' or 'I'm doing this because I want to,' when in reality, they are doing it for the sake of the company.They might say, 'I'm just doing what I want,' but in the end, it benefits the company and, by extension, society. It is these multifaceted aspects of human nature that are truly fascinating.

Even if you think, 'This person is pathetic' when looking at them in the short term or from a narrow scope, when you look at the big picture, these people are the ones who keep the world turning. We live by supporting and cooperating with one another. The world is made up of these lovable people who have both a front and a back, and they are the ones who do both good and bad things.

That is why I think human beings are such interesting creatures.