Enterprise sales pitfalls: Even if the CEO loves your product, you can still lose the deal

by Steli Efti

CEO_Enterprise_Pitfalls

If your startup is selling to the enterprise, always make sure to identify and understand all the stakeholders involved in the deal.

As a founder of a technology company, you might find yourself faced with a new challenge: breaking into enterprise sales. Few people come into this game with a playbook in hand.

I sure as hell didn’t, and I learned my lessons the hard way.

One of the most painful (and expensive) “learning experiences” a startup can go through? Investing months of work into a deal only to see it fall apart in front of your eyes.

The CEO is the beginning, not the end of the deal

Startup founders often get introductions directly to CEOs through their investors or advisors. Once a CEO (or any other senior executive) takes a meeting to listen to their pitch and gives them buying signals, they think that the deal is almost done.

What could be more important than having the CEO of the company herself approve of the deal and be invested in its success, right? A lot!

The CEO is only the beginning, not the end of the deal. CEOs tend to have one or two major strategic initiatives they champion every year. Everything else will be delegated down the organization to a more appropriate person. So even if the CEO likes what you do, she's not going to be your internal champion.

A successful meeting with the CEO will most likely end with an introduction down in the organization to someone else. Now the real selling begins. 

There are two steps after the CEO wants to buy your solution:

  • Step #1: Selling all other stakeholders involved in the deal
  • Step #2: Selling the person that's going to manage the project internally

Step #1: Close all the stakeholders

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 use the virtual close and 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.

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 dialogue immediately to learn what they will need from you to help move the deal forward. You can't afford to be passive.

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

Step #2: Close your internal champion

The person who will ultimately get your project put on her plate and become responsible for its implementation doesn’t always share the CEOs excitement for it. She already has a pretty full plate and from her perspective, it might just look like more work with very little upside to her.

You need to convert that person 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.

Want to learn more about enterprise sales? Read up on The 7 Essential Rules For Successful Enterprise Sales.