Anime News Network has posted part 1 of a new series about how anime is licensed. Part is is quite long but it is very informative and here is an excerpt.
Producers cold-call or cold-e-mail companies that have released similar shows in their areas of the world before, and ask if they want to take a look at their shows. This is a big job, and requires pretty decent English skills. If a producer is too small to handle it themselves, they might hire a sales agent to handle this part of the process. They prepare screener copies, packets of flyers ("one-sheets") promoting new shows, and fancy catalogs of old stuff that might still be available. Some distributors like to license a bunch of TV shows or movies at once, so having a large amount of good, available content can be a real asset to getting a deal done.
And then there are trade shows, such as MIP-TV, American Film Market, TIFFCOM (attached to Tokyo International Film Festival), NATPE (National Association of Television Program Executives), and just for anime, Tokyo Anime Fair. These trade shows are huge affairs that are, by day, semi-formal meetings at booths (complete with info packets, screeners, and business cards), and at night turn into fun, casual grown-up talk.