Closing that First Enterprise Deal

Elizabeth Foughty

As a b2b startup*, your first big enterprise deal is the THE deal. Your Everest. It’s the one that takes you from an idea to the big time, and catches the eyes of investors.  It adds credibility, so other enterprise customers feel more comfortable signing on.  A charismatic and/or determined founding team will be able to get in front of enterprise customers.  Then…it won’t close. 

*also applies to midsize companies going after BIG fish for the first time.

Sure, you’ll get a proof of concept or pilot, and it will be brilliant. Then the deal will fizzle out.  Why? Your product performed, did it not? The results were clear. 

Here’s why. 

Vendor management. And their job is to ensure the organization makes good business decisions. Will it seem like they are just being a big blocker? Yes. Does it make complete sense they want to thoroughly vet multimillion-dollar deals? Also yes. 

Here are the common hurdles you’ll face and need to overcome to get that deal across the line:

Cyber Security.  If you don’t have a robust, enterprise-grade cybersecurity plan, you need to sort that out. Enterprise customers do not mess around here (and they shouldn’t).  If your widget is going to touch or impact their systems in any way, or you’re going to hold their data, you cannot hand wave this away as a future problem. 

A realistic  implementation plan.  If your product has any sort of complicated implementation, or even just one that is more complicated at scale (pro tip: they are ALL more complicated at scale!), you need to lay out a plan that your customer believes. This means it better be carefully considered, not overly optimistic, and concretely laid out. 

A support plan.  Do you have a plan to scale support? Is it logical? Is it built on more than just “hire more”?

A robust roadmap.  This roadmap should NOT be built around them.  Why? If it is, what you are becoming is a one-off bespoke built shop, not a b2b business. Some companies may find an advantage in that and work with you anyway, but it’s probably not in your business model to only support one customer.  Other companies (smart ones) will soundly reject it, knowing that it means your company likely won’t succeed and you’ll just become a vendor that has to either be bought/managed or changed out. 

Pricing. You need a pricing mechanism they believe is realistic to keep you in business, but also reflects economies of scale. If they do the math and realize the deal size doesn’t cover the 17 hires they think you’ll need to get the job done, it simply won’t fly. 

Patience. Enterprise deals take time.  If you need this deal to close in 4-5 months because it will make or break for success, you need a new plan. 

Enterprise customers are taking a leap with you. It’s likely some other enterprise shop has offered a (pricey, klugey) solution that is not as cool/innovative/game-changing as your widget or the customer has a choice to do nothing.  From where they sit, these are lower-risk options. Because they are taking a leap with you, you need to prove to them not only that your solution works, but that you’re also packing a parachute.


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