Our first customer was a lead from one of my co-founders. He'd been in another company a few years prior in the same space, and that company went bust, and the

Our first customer was a lead from one of my co-founders. He'd been in another company a few years prior in the same space, and that company went bust, and the customer needed a new solution. An easy first sale. Later sales proved to be extremely difficult. IIRC our original price list ranged form $15k to $100k. The typical sale included hardware, a 1U rank-mount server that we pre-instated our software on. Why were sales so difficult? - Enterprise sales can take a long time to close. I think our average close time was a year. That's not surprising when you think about the process most companies have to go through -- getting buy-in across divisions, waiting for an annual budget period to arrive, etc. Educational institutions took the longest -- over a year. You need a lot of runway. - Enterprise sales are very high-touch. Lots of phone calls, lots of demos, lots of on-site visits. Prepare to buy lots of meals for decision-makers! It's reasonable for a large company to want to spend time to get comfortable with a start-up... you're competing with HP, Microsoft, EMC, etc. for these customers, and none of them are going away anytime soon, but your startup needs to prove it's real and has staying power. - During one of your first get-to-know-you calls, I highly recommend learning about the internal process of the company. What's the signature authority of your contact? Who has to sign off to approve a payment of the size you're thinking of? It's not uncommon to believe you have all the approvals you need, and actually be wrong. We had situations where we installed gear on-site and later learned that a VP needed to sign a check of that size. Don't be rude, but make sure you ask the right questions. You may need to get the name of someone in Payables to get the real deal. - To avoid the lengthy approvals process... a trick I liked was to make a custom product just below the expense limit cutoff. For one company I talked to, they could authorize and expense anything under $1k, so we made a product that was $1k/month that they could pay with a credit card and expense. - Contracts are part of the long lead time. Expect lots of modifications. If you don't have an attorney handy, this can be a real expense. - Source code escrow came up a lot. You may want to investigate options ahead of time and bake the cost into your pricing structure. By the end of my time there, I was convinced that enterprise sales weren't worth the trouble.