I must say this is a really crazy aspect of the job market: everyone knows the market is tight, that most philosophers are, in one sense or another, "under-employed" in their first position [even when it is tenure-stream!], and that multiple searches over multiple years are the norm--yet still there is a tendency to draw unfavorable inferences when the job seeker has a PhD that is several years old, and no tenure-stream job.
If this is so, there are far too many people in the philosophy profession who are not taking the trouble to apply basic reasoning and critical thinking skills; and that is indeed sad, given that, if there's any profession that prides itself on reasoning critical thinking, it's philosophy.