Its a question that was brought up at HighRankings Forum, "If most of the sites competing to be in the top 20 google listings for my keyword are directories, do I need bigger guns than if they were not directories?" The thread gets into PageRank, link building and normal optimization. But let's really think about it.
A directory is a "hub". Hubs are important, and search engines know that - and rank them well. Authorities are possibly more important then hubs and tend to rank above hubs, on many occasions. For this individual to rank above a hub (directory) for a search term that is very hub centric, he would have to become an authority. Becoming an authority can happen a dozen of ways, right now links are fairly important.
I question the search term this individual is trying to rank well for. If the first 20 results are all directories, maybe he is trying to rank well for the wrong keyword phrase. Just a hunch, without knowing the specific keyword or site in question.