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Shameless plug: we @Countersoft actually compete with Jira all day long. But I hear you - there's not many enterprise grade issue trackers (that don't suck).
Nothing shameless! So how does one get a start selling software to enterprise? Granted your product is SAAS so I suppose that reduces the barrier. I spent 6 years doing Enterprise consulting but as a workerbee I don't believe that gives me much of a leg up, compared to say someone who was an exec. I don't want to start cold calling/emailing former clients and coworkers :)
Over half our sales are still On-Premise: download and install. Shock. Horror.
From a tech standpoint that's tough because the same web app has to run under Windows IIS and then scale to handle SaaS customers in our own cloud setup.
Barrier? You should see the crap you have to handle in order to just install .NET web app onto say a financial company's hardware. SaaS guys have it easy!
In terms of Enterprise Sales we have lead generation activities with inside sales folks who provide product demos. Took a while to get it right. Trade shows, banners, magazines - none of this stuff works for us in enterprise sales, where customers hand over tens of thousands of dollars for a software license.