It happened to me at both my startups and it was relatively easy to do. There are a several keys to winning these deals:

1. Call it a pilot. Enterprise companies love pilots. If it doesn’t work well, then not the end of the world.

2. Find the person at the enterprise company with the most to gain and get to know them well. Dinner, drinks, coffee, whatever time they are willing to spend with you, take it. Get on a jet, be there, make them know how dedicated you are. Learn from them on what it takes to sell into that company and more times than not, they will root for you and help you get in the door.

3. Make sure the company knows how stable you are. Even though you are relatively small right now, let them know about the long-term vision and what your investors have at stake.

4. As a founder, you are their account manager for life. Make sure they know this. You will answer their call before your family’s for life. You will have dinner with them a couple times a year, know their birthdays and kids names, become friends on Facebook, everything.

5. Don’t mess up. Over communicate, under promise, over deliver. You only get one chance, maybe two if you’re lucky. Make sure your main contact at that company is successful, no matter what you need to do to ensure it.

Culled from – Quora

Written by Jason Weingarten, Two-time SaaS veteran selling software to the Enterprise and Education spaces.

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