How to get your first Enterprise customer after having several SMB customers

You have read my article on the differences between Saas enterprise and Saas SMB you are currently selling to SMB and are wondering how you can get your first Enterprise customer, I will try to help you do so.

If you have read my article carefully you know that what you are trying to do is hard in the long run, sustain both kind of customers (SMB and Enterprise) in the long term requires a lot of agility and excellence in all departments of your company

Understand that selling to this new type of customer is completely different

You are used to communicate with your customers through SEO and digital marketing, none of that works with Enterprise customer, they care about being able to talk with someone. Someone who understands their problem, someone who listen to them more than solve their issue. In bigger company, the decision maker is not the one who is going to use your product, he doesn't need to know how the product work, the product features, the number of steps it takes to change an image,...

They need to know, the ROI of your product and if they are aligned with your vision (sometime you also have some legal requirements or certification issue). None of the those 2 elements need to be true. The ROI can be wrong but the customer need to beleive it is true, the vision can hide a malfunctionning product. This is the sad trough of enterprise sales, your job is to present the topic in such way that the customer is wanting to hear about it. After they buy your product they will most of time stick with it for several years and will almost never ask you back about the features they talked to you about during the sales process. They are used to care more about the platform being able to scale with their volume, and their useless pixel perfect design, and other things which are not helpfull to achieve their objective.

Big comapnies can't take risk, a legal risk can be the end of their business, a scallability issue could be a nightmare for their communication. Big companies move slowly, just the fact of changing of provider is a huge risk for them.

Let me give you an example, imagine you are Facebook and you notice that your product ( is less and less used by people and you understand that this is such way because people think the design is too old school, and young people don't indentify with it anymore because they prefer dynamic product like TikTok, what will you do ? Will you try modify your design to be more dynamic ? Probably not, changing is probably more risky than keeping thing as it is, you have quarter forecast to make and doing such change will probably put you in the dark regarding your future. So you have two options to continue react:

  • You change things slowly, you start with updating the design of messenger, it takes you 6 months, then you start changing the group product, and so on, the changes will take you years to achieve, and probably after a few years (before you complete the product revamp) the design will again not be matching user expectation
  • You buy Tiktok or Instagram or Snapchat or ... and let them the autonomy to keep growing without interference

A small companies on the contrary has 3 customers, it doesnt really care if it has to lost them to migrate to a better product, this company is therefore more agile because it has also nothing to loose.

Remove from your brain how you are used to sell to small businesses, enterprise requires a complete different approach.

Adapt your pitch

If there is only one thing that you need to adapt it is what you are pitching to your prospect, you are probably used to talk about individual features, this is wrong to do in enterprise, this is the last thing you want to do. What you want to talk about it the vision, what is the vision of your products, what is the vision of your company, what is the vision of your customers. Enterprise customers are looking for long term reliable partner, they want to feel that you understand their problem and that you are long term engaged to help them.

So first, talk about your vision, if the prospect is talking to you about a feature, answer quickly and redirect the discussion that saying that this is not the most important.

Usually the sales cycle in enterprise is splitted in 3 phases:

  • First phase, qualification of the prospect : does the prospect have the same vision as your company ? (usually a phone call)
  • Second phase, understand the prospect issues: You need to talk to them to understand what are their issues, what they want to do, how they want to do, when they want to do it, .... The prospect needs to feel listened, they need to feel ok sharing with you their issues and wanting to collaborate with you, they should share with your their vision, understand your positioning and seeing that you are here to help them and you have time for them (a physical meeting, with usually a generic presentation from you, but this is just a support the meeting should be interactive)
  • Third phase, the proposition : you explained to them what you have to offer them, that's also the good time (if necessary, a lot of enterprise softwares are sold without the prospect even seeing the product) to make a demo of few features that they would be able to use, the ROI of the product, the structure of your organization, the strutures of your futures exchanges ( for new features contact this email, for technical issue contact this other email, lets have a regular call every quarter,..., dont hesitate to promote, for example, a simple software engineer to Head of Tech virtually to just make your organization look more mature) and then the price of your solution

At no point of the process you should tell about your flaws, you can talk about your limits, but never acknowledge a flaw, because usually a flaw is not a really a flaw, it is more a limitation. You should be confident about what you are selling, the prospect is taking some time with you, so they are thinking you are a credible solution and you should act as one. Never forget that other competitors may have 10 times more customers and employees than you, the reality is that they are not agile anymore and their software is lagging probably a f ew years behind yours. Position yourselft as a leader of your sector and dont be demanding. if the prospect is asking something very different than what you are offering, it means that you did a bad job at phase 1 ans phase 2. You can adpat your vision, but don't change everything, keep your culture and authenticity

To sum up :

  • Be confident you are a credible solution
  • Don't talk about your product, instead talk about your vision
  • Listen to the prospect and create a trustfull discussion
  • Don't accept everything, stay as you are. The product is not going to change they need to adapt to you

Accept the consequences

Going after enterprise customers is going to change many things in your organization, you will probably have more contact with them than you used to have with your old customers. They will not call you when they have an issue, you will have to call them to ask them if everything is going well instead. You will have to get used to talk about your vision with them, and expect them to answer slower to your requests.

You will have to keep building on a strong personal relationship with them instead of just one centred on the product. This is not going to be easy, even for your small organization being able to make all those changes is going to take time, and sales processes with enterprise customers are always longer, it is not weird to have a sales process taking more than a year

This article also applies to less Saas business, and any business in general even though you will need to adapt things to your industry. But the principles are going to be the same