Who is the right sales hire?
About as tough to ask as who would be a good wife (or husband)..
You probably need to answer 20 or 30 questions before you even contemplate--
Where is your product ( pre rev, rev, ) and what product/market expertise does your rep need?
What are your organizational thoughts... are you hiring a sales person, someone who has Bus Dev skills, someone who follows up leads or has their own network, someone who is your sales guy or member of the management team... are you hiring your "VP" of sales for now or someone who can be the VP when your firms is 5-10M in sales... is he a channel person? partner person? direct face to face guy? Is he expected to close or just get the lead qualified and through the first level calls...
What is your financial model and compensation ability , What can you afford now?
What skill sets do you want added to the team to complement you... For example many times good sales guys are way more experienced than the founders in a startup... Hence they can add value in funding efforts, product development, production/product roll out guidance and so on. What additional skills is your firm short on.. One of the classic mistakes that founders make is trying to hire sales guys in their own image... "get me a young smart guy 3 years out of college like me" when they would be better off with a 40 year old who has sold in the market and has contacts or connections who can at least commit to take prototypes of be early adoptors... and again this is dependent on the rest of the team... ( Perhaps because I am senior, I preach that every entrepreneurial team should have at least one grey hair around )
hope that helps