Selling.  It hurts, which is why sales people tend to get paid tons of money.  You’re subjected to near-constant rejection, have to deal with ambiguity on a regular basis, and have to be a master at overcoming sometimes ridiculous objections.

It’s just like looking for a new job.  How’s that for a pep talk?  Now on the plus side, when you’re job searching you have an advantage over most sales reps – you built the product, you know it better than anybody, and there are sites where potential buyers literally list what they’re looking to buy.

You should still approach it like a sales call – reps who know how to close deals, know that the sale is won or lost before they even stop foot into the prospects office.  The best ones know that this happens even before the first contact to set the appointment.  They do their homework, know the targets needs (pains, really) well, and know who the key people are.  How often have you just responded to job postings with a canned letter?  If you do this on a regular basis, stop right now.  It may seem time consuming to research a company just to target your cover letter to the right person, and to be able to tell that person why you skills will make their company better, but it’s worth it.  Compare the net amount of time you spend sending our that canned cover letter, over and over, and tracking where you sent it in a spreadsheet, following up with a call, etc, to investing some time on the front end that will actually get someone to pick up the phone and call you, and I think you’ll see that the front end stuff is a time saver.  As an analogy: my father was, among other things, a highly skilled carpenter.  He worked with some pretty expensive woods, and this made him conservative about simply hacking away.  He’d spend hours researching the design, planning the cuts, practicing on cast off wood, before he began his project – the cliche here is “measure twice, cut once”.  Getting a better job is -frankly – waaay more important that making a fancy wooden clock.  You should prep.

Once you’re in the house, as it were,  come prepared – as an example: bring copies of your resume.  It’s likely that the interviewers all already have them, but if they don’t you look prepared.  Fact is, even if no one needs one, not coming in with one makes you look like you miss important details, and that can be a strike against you (seriously – one of our managers just ruled out a candidate, and that was one of the reasons: he felt it spoke to the overall impression that the candidate wasn’t that serious, and/ or just didn’t get it).  

Anticipate objections.  You should arrive knowing a ton about the company, the position, and where your experience isn’t an exact match.  Expect to be challenged here, and practice your responses.  Don’t give long-winded, defensive sounding answers, but have a quick, friendly rejoinder that allows you to segue back into why you’re a good fit.  Come from a ginormous company, and now you want to join a 100 person, hip, cutting edge Web company?  No problem, because while you were there you were always putting your hand up for duties that fell outside of your box, and gained a reputation as somebody who was great at doing more with less – and you’d love to be somewhere that you didn’t get looked at like you had 3 heads for being scrappy and resourceful.  Somewhere like, say, ZoomInfo….

Probe – that means, ask questions that require answers beyond a simple yes or no.  Ask questions of everyone you see – never, ever say you don’t have any questions.

And finally – ask for the job.  Close people.  Show them some love.

There, now you’re a sales person.  Rock on.