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Go enterprise and don't get lured to the "enterprise for 1.99" business model, propagated by a few exceptions that succeeded (e.g. 37signals). It's a lot "easier" to scale charging proper money for B2B products than betting on scale...

I wouldn't say 37S were "enterprise" , they started at the low end of the business market. I'm guessing a lot of their initial customers were freelance rails developers.

They do have enterprise level customers but that's more of a "trickle up" thing.

You have to hire out execs from previous enterprise companies, or work at one and get to know people in the company (as well as their problems) that you solve with your technology.

not necessarily. Cold calling works rather well, in most products. The sales process is definitely long (several months), but it does work... (my first company was a B2B for companies with 50+ employees and we didn't know anyone in the industry)

That said, knowing someone definitely helps. A LOT.

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