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This is why you need a dedicated and experienced sales person. Selling to a small company is one thing, but selling to a larger customer is an entirely different skill set. And then selling to enterprise is even more different. The sales cycles differ tremendously depending on how large the organization is.

If you are targeting SMBs, you can get away with direct sales, etc. But once you get into the "bigger fish", the sales cycle lengthens incredibly, as do the requirements from the buyers.

One of my previous employers made the transition from selling from SMBs to enterprise, and it was a difficult transition. Our product was usually bought by a department head that required it, and it would spread across the organization organically. However, once we entered enterprise companies, instead of talking to the department heads, we needed to talk directly to the CIO/CTO, who would make the decision on behalf of the entire company. This required a lot more patience, and a completely different skillset from our salespeople.

So in the case of the OP, trying to land a big fish by talking with contacts like this is likely a huge timesink, because experienced salespeople will eat guys like him for breakfast. If you're going to target bigger fish rather than smaller shops, it's best to get someone who knows exactly what the process is and is actually focused on sales. The charm of working with a startup is lost on bigger customers, who have bonuses based on uptime, SLAs, etc.

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