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A guide on Enterprise Sales – What it is and how to scale it?

Enterprise sales was a distant idea to me. And writing an article on it, almost an impossible task for an enterprise newbie like myself.

And so I decided to consult my friend Jay, an enterprise sales expert.

What is enterprise sales?

“How do you manage to excel at Enterprise Sales, Jay?” I asked.

And so he presented me with a detailed guide on how one can leverage Enterprise Sales to grow their business and scale it.

“It’s quite a simple idea, Parijat, if you think about it. It’s just a matter of practice and skills that you can develop in no time. This is how I make the best out of Enterprise sales–”

For me, sales is all about building relationships, as it should be for every sales rep out there. After all, how do you think you can sell your services to a stranger who can’t even trust you?

When it comes to Enterprise Sales, nurturing relationships is everything. And nurturing one’s relations starts with building a rapport with your clients first.

Do you know what I say when I go to a prospect for the first time?

“Help me help you,” just like Jerry Maguire.

I have met many salespeople who wish to excel at Enterprise sales but aren’t able to. The reason for their failure? They don’t ask enough questions. Especially the right questions.

So let’s start with the basic ones.

What is enterprise sales?

“You can’t run a business without taking risks.”- Millard Drexler

Enterprise Sales or complex sales are the ones that involve long sales cycles, multiple decision-makers, and higher levels of risks than traditional sales.

To put it simply, Enterprise Sales involves large-scale corporate solutions, and since it takes a long time to close every deal, it comes with its own set of risks.

A typical enterprise sales model is marked by the following:

  • High risks
  • Many stakeholders
  • Long sales cycle (6+ months)
  • High investment
  • Complexity

Now that you know the definition, your question here should be, “Is Enterprise sales right for my business?”

As a sales rep specializing in Enterprises, I would like to tell you that this segment of sales is not fit for just every business. But there are ways in which you can know if you need it for yours, and if the answer is yes, then how can you scale it.

With the high risks that it puts up, enterprise sales aren’t generally preferable for startups, and are more common in mature businesses that are already generating good revenue, and have the potential to take risks.

However, in certain situations, enterprise sales can be just what your business needs!

I, for instance, sell a CRM for all sorts of businesses. Since I work for a SaaS company, my service becomes essential for large corporations, where my solutions directly impact their business operations and strategies.

Let’s go through my sales routine in order to understand how Enterprise sales helped my company scale its growth while providing value to our customers.

How I sell services to enterprises

Before I reach a prospect, I tend to study about them and their business, and above all, I try to figure out if they would need my services, and if yes, then how will I be able to help them.

Yes, your duty as a sales representative is to help your clients. You either make them realize there’s an issue they need to resolve, or you provide a solution to a problem they already know about.

Here’s the set of questions I ask myself before setting up a meeting with the prospect:

1. Onboarding

What’s to think about onboarding, you’d ask. However, this step is indeed the toughest of all. All your sales processes end at this stage, but this is where your service starts to take shape.

Will the onboarding process be smooth, without causing any trouble to the client?

I always ask this question, because, for any sales rep, the client comes first.

2. Security

What if my service causes any security issues to my clients? Is it going to be safe for them to use my services?

The SaaS product that I sell, as mentioned above, provides top-class security to my clients. Hence, I am covered on that part. Are you? Think.

3. Post-sales support

Your role does not end when a sale is made. In fact, providing proper post-sales support to your clients is an important part of maintaining good relationships with them.

Prepare yourself for any objections and queries so that it doesn’t come as a surprise later.

4. Proof of return on investment

When a company invests in a service or product, it expects good returns on it too.

For example, if my clients bought our CRM solution for their startup, they would want better results from it, like data management and automation. Ask yourself if this investment would be worth it for your client.

5. Automation

Imagine how your client would react if your service adds to his workload instead of lessening it? Not a good scenario to imagine eh?

I am always certain that my clients will always get the best automation solution if they buy my CRM, hence, I rest assured, and so are my clients.

6. Social proof

To date, I have sold my solution to a number of companies, and so when I am about to approach another one, I can always boast that my clients are happy with my solution.

Think of it, do you have any social proofs to give to your prospects?

Enterprise sales require a lot more thought than any other sales model because this one needs good rapport with the clients. Since the sales cycle is so long, nurturing relationships with your clients become an essential part of your business.

Now, what next?

This part of the whole process is what I call, self-introspection (sales version).

Once I am done introspecting and analyzing my own service/product, then I begin to think of the steps involved in enterprise sales.

Four D’s of enterprise sales

Sale is a process. And enterprise sales, a very long one. I have segmented the whole process into 4 stages, or four D’s as I like to call it.

1. Discovery

“You’ve got to have a problem that you want to solve; a wrong that you want to right.”- Steve Jobs

This is where I reach my prospect, learn about their business and try to understand the problem they are trying to solve, and then help them solve it with my service.

Not boasting here, but I have a quality that makes me good at sales.

I ask a lot of questions.

I ask my prospects about their organization, mark their pain points, and understand their requirements. This helps me get a clear picture of how my service can provide them a satisfying and long-term solution.

My advice to all the sales reps out there: Ask your prospects what they seek, and then pitch your service/product as a solution.

Remember, you are selling the solution, not the product.

2. Diagnosis

Since I ask a lot of questions, I now have a thorough idea of my client’s business, gaps in it, and their goals to fix them.

The enterprise sales cycle is tiringly long, but it has its own benefits too. A longer cycle means you get more time to indulge in detailed research on their business and diagnose their problems. 

With a good diagnosis, comes a customized solution to their problems.

3. Design

This is a crucial step for me or any sales representative like myself. This is where I combine my knowledge and understanding of my client’s business with the solution that I have ready for them.

Once I am done with my research, I sit with my client and present my solution to them, and customize it according to their needs.

With Salesmate CRM, I provide tailored solutions to every client, no matter which industry they work in.

4. Delivery


After all those months of sheer hard-work and rapport-building, this is where I deliver the solution to my client. And because the solution is made exactly according to their requirements, I am pretty sure that it’ll satisfy them.

As a sales representative, it is necessary to understand that your goal is not only to close a deal but also to help your clients achieve theirs.

“Sale is an outcome, not a goal. It’s a function of doing numerous things right, starting from the moment you target a potential prospect until you finalize the deal.”- Jill Konrath

Now that you know how to get better at Enterprise sales, it’s also important to know why it is a good business model for your organization’s growth. Hence, the next important question.

Why is enterprise sales important for your business?

Enterprises show you the real money. Bigger the client, the larger the revenue growth.

It doesn’t really matter whether you are a startup or a mature business, if you have the right team of sales representatives excelling at enterprise sales (like myself, not boasting), then it’ll be a no brainer for you to scale your business with this model.

All it takes is good relationship management and nurturement.

If you are already kicking in the market then finding new clients won’t be a hustle for you, however, if you are new to the business and seek bigger clients, then you must go with good referrals. After all, stats show that 84% of buyers prefer buying from referrals.

Jay’s words of wisdom

Steve Jobs had once asked a question that gave every salesperson the base of their pitches-

“How does somebody know what they want if they haven’t even seen it?”

It is up to the sales reps, us, that we show our prospects where they lack, and then provide them with a solution.

But how do you get them to trust your solutions?

Of course, by building a strong relationship with them!

In sales, it’s all about relationships. And in the world of Enterprise sales, that is all it takes.

Parijat Lamba

Being an avid reader, Parijat developed a keen interest in writing at a very young age. She's passionate about topics like Spirituality, History, Psychology, and Philosophy. She's now a Product Specialist at Salesmate and strives to write her own novel someday.

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