I agree. It sounds like you are asking this because he seems like he's almost the perfect fit, but you know he isn't and you want us to tell you he is not so yo

I agree. It sounds like you are asking this because he seems like he's almost the perfect fit, but you know he isn't and you want us to tell you he is not so you can feel better about it. I've been there, having an almost perfect fit immediately available is the easy path, otherwise you have to hunt and do dirty work and it can take awhile and you want someone you know well and you want it now, that is understandable. It doesn't sound like the guy wants to do what you want him to do, and it doesn't matter if you think he'd be awesome at it if he'll never do it, or only do it half-assed and begrudgingly. You can't be a cofounder with one foot in the door and one foot out. He's gotta be all in. I've had promising startups that relied on co-founders with expertise, but they wouldn't take the leap and good advisors said the same to me, so I bailed and they never went anywhere. A cushy job is very addictive. You have a need so the best thing you can do is find someone who will specifically fill that need with a passion. You probably don't have money to pay them, so you are looking for another way to compensate, but that's the rub. Good sales people will want to get paid, unless they are insiders who know they can make it work and just want to suck the equity from you and try to make the startup theirs. You could almost make that work, but good luck with that scenario. It's hard to bring in a cofounder this late, especially if they won't go all in, you are looking at giving away at most 10-15% if they really are awesome, all-in, and stay for 3-4 years (and probably not getting paid). If they are bringing money with them to invest, then it changes a bit.