"Successful enterprise salesperson happy to join a cash strapped startup" is an oxymoron in more than one way. Other posters explained it: these salespeople expect big support, big budgets, ads to generate leads, junior staffers to screen the leads, etc. They also expect a lot of cash compensation: virtually all such people I have ever met usually like flashy and expensive lifestyles, because in what they do the appearance of success is one of the factors that breeds success. I remember one guy who seemed very enthusiastic about joining us, but then the deal fell apart because in his contract he absolutely would not budge from first class air travel and Jaguar-class rental cars.
Then we decided to do it ourselves (the founders). We networked the hell out of any friend we had, and our intro to prospects was "Look, we are not sales guys, we are entrepreneurs. We think we have a kick-ass product and we'd love to show it to you, and since we are still small the price to you will be super-cheap compared to the competition if you help us improve it to fit your needs." That way we eliminated a lot of issues and we tried to compete on a different playing field.
The result: we got clients to work with us, and the sales guy we hired never managed to go past a first meeting.
I did a startup some time ago where we were four founders. One of them was an excellent enterprise sales guy. In his previous job he had managed sales in excess of $100 million on a yearly basis. His job was, of course, to push the product. It didn't work out because he was used to a big organization that took care of everything from planning his meetings to serving him coffee. He simply didn't get the startup culture where you have to save every penny you've got, and do everything yourself with noone to delegate to.
We ended up buying his shares and he went back to big-corp where he was more at home.
I'm not saying that all enterprise sales people are like this, just that it's something to be aware of.
Buy quality lists and then have an inside sales person qualify them and setup the appointments for the outside sales rep.
The good inside sales reps have different skills than the outside ones.
This is not to say there aren't good sales people from well known companies, it's just that they probably had it pretty easy so they wouldn't know what to do if they had to fend for themselves.
Question: Which outstanding salesperson would join a startup that had a low base salary, no draw for salepeople, no proven sales model, minimal marketing material, a moving target for a product, inexperienced management, no sales peers, no leadgen team, no client base to sell into and reference from, an unproven compensation scheme, etc...
From a sales point of view (selling the job to someone good), you have a pretty terrible product. :-) The only way to get around this is to pile on tons of equity, find a sales guy who is passionate about your product, or find one who is bored and thinks startups would be fun. Even then, it's a tremendous leap of faith and your startup has to feel like a likely home run. Salesfolks are financially motivated (usually) and you have an uphill battle here.
The other alternative is to find a "diamond in the rough" - but obviously that's hard to do. I honestly think that's the only alternative if you can't afford the real deal-- because the best guys will run away screaming or laughing. A startup is a terrible financial bet for a salesperson.