How do you become successful at enterprise sales?

Q: How do you become successful at enterprise sales?

A: Steli Efti,


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You become successful at enterprise sales by getting to know the unwritten rules (which I attempted to write out here):

Rule #1: Expect long sales cycles:

It can take 6 to 18 months between establishing the first contacting and closing a deal.

In any organization there are always a lot of hoops to jump through before a sale is actually made.

Make sure to have a realistic roadmap of their typical purchasing process. The simplest way to do this is to ask: “Once you have decided to buy our product, what typically needs to happen next to get the deal done?”

Realize that selling to the enterprise is a complex job that can take anywhere from six months to three years.

Do your homework to make sure that you don’t invest all that time in a bad deal. There are no guarantees in this game, but the stakes are too high to be sloppy at any step in the sales process.

It’s your job to manage the complexities and support all stakeholders in moving the deal to a close.

Rule #2: Realize deals might fall apart (even if you do everything right):

In enterprise sales, you can lose a sale for a multitude of reasons you have zero control over:

  • the main person you’re selling to leaves the organization
  • changes in the economy
  • changes in the corporate strategy
  • etc.

Rule #3: Sell to multiple stakeholders:

No matter how high up the person is you’re selling to, you need to sell to different groups of people within the enterprise, up and down the hierarchy, vertically as well as horizontally.

You need to understand different groups have different needs. And you need to cater to all these groups. Even if the CEO tells his team to buy your product, if you don’t have buy-in from the IT dept, you might make the sale but your product won’t get implemented correctly and you’ll lose that customer.

You need to be able to check off on all the question marks of all the different internal groups that are going to be involved in the purchase of your product.

Legal, procurement, the technical team that’s going to have to implement your solution and any other department that’s going to be affected by the purchase of your product.

Reach out to them early and start a dialog immediately to learn what they will need from you to help move the deal forward. You can’t afford to be passive.

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Rule #4: Don’t underprice:

Many startups breaking into enterprise sales want to offer heavy discounts or even do a freemium model. They (falsely) think that pricing will prevent an enterprise deal from happening.

Lowering the price of your product, or even giving it away for free will diminish perceived value and importance of the deal for the entire organization. “Free” isn’t valued in the enterprise the way it is for consumers.

Rule #5: Decisions are made by employees, not “the company”:

Employees don’t necessarily make decisions that are in the best interest of the whole organization, they often make decisions that first and foremost benefit their own career. Keep that in mind when selling them on your solution/product.

You need to convert that person who ultimately is responsible for the implementation of your product into a real internal champion or you have no chance for success, no matter what the CEO said in your initial meeting.

Once you know who the person is who will be responsible for managing your product internally, do everything you can to sell that person on the benefits of your product to the entire organization, but even more importantly on the benefits to her career.

Find out how you can support and empower her to promote your solution within the company. Find out how you can connect the successful implementation of your solution with her own, personal goals and ambitions:

  • What goals does she have and how could your product help her accomplish them better?
  • Which objections and fears does she have in regards to your project?
  • Which objections will she encounter when implementing your solution in the organization?
  • What is the best way for you to empower her to succeed with this new project?

You need to invest a lot of time and effort into the relationship with your internal champion. The CEO might have opened the door for you in the organization and gave her blessings, but it’s ultimately the project manager that will turn your product into a massive success or a devastating failure. Ignore her at your own peril.

Rule #6: Start doing enterprise sales before your product is ready:

It takes such a long time to close an enterprise deal – so start as soon as possible. You don’t need to present a perfect product.

All you need in the beginning is an idea. The first time you talk with them, you’re not going there to make a sale, you’re going there to get advice. Tell them you’re developing something that could be really useful to them, and that you’d like their feedback and input as you develop things.

Keep them in the loop and use the time it takes to develop your product to build a relationship and establish trust. That way when you’re ready to launch, some enterprise customers will hopefully be ready to buy.

Rule #7: Start mid-market. Move up:

Gain some momentum in the SMB space and move upstream into the enterprise world as your product develops, your team grows and you establish capabilities to service large enterprise customers.

There are some common enterprise sales mistakes – these questions can help you to address and fix these mistakes early on:

  • Who are the key stakeholders involved in this deal?
  • On a scale of 1 to 10, how much does each stakeholder want this deal to happen?
  • Does each stakeholder see an opportunity in their career for this?
  • Is each stakeholder excited and passionate about your solution? Have you sold the vision to each person?
  • What are major objections different stakeholders have?
  • Do you manage the onboarding process and pilot yourself and are actively involved in making them work for your prospect?
  • Do you have clear metrics to determine how the prospect defines “success”?

This question was originally answered on Quora on July 7th, 2014.

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Kayla Kozan

Kayla Kozan

Director of Marketing at Ideal
Kayla spent the last few years studying Marketing and Entrepreneurship on 3 different continents. Now covering the latest in predictive analytics, workplace diversity and big data. She has a keen interest in tech and discovering underrated brunch spots.
Kayla Kozan