This is the second in a two-part essay. The first part may be found here. 
--In the end -- and please know I hate this language as much as you do -- much of your preparation for the job market is about how best to sell yourself. You do need to take some time to read the letters from previous applicants in your department and figure out how to position yourself with respect to your chosen disciplinary field. Who is getting jobs? At what sorts of institutions are they getting them? What are they doing right that you can steal? Where do people seem to be going wrong?
If you're applying in English, for instance, at a minimum you need to be able to make the case that your project speaks to the concerns of a fairly traditional English curriculum, as nearly all the jobs that are available are in departments that are much more traditional and canon-focused than the work grad students are typically doing in their dissertations (especially at a place like Duke Lit).
You also need to show you bring something new to the table — secondary and even tertiary desirable specialties beyond what the job ad nominally requires. (If you have any remotely plausible case to claim your work is "digital humanities," do so.)
You also need to show you can teach across your field generally, not just in your chosen subfield. It was very common, even with postwar and contemporary literature jobs, that I’d be expected to teach introductory and survey classes, the terms of which are quite various. For some 20th-century American literature jobs, for instance, there is an expectation that you will be able to teach American literature surveys extending as far back as the Civil War, or further; at other
institutions, there is an assumption that any hire, regardless of specialty, will be able to teach generic English-literature surveys that include English, American, and world literature in translation, as well as all genres: poetry, fiction, and drama. Be ready to show you can do this. If you haven’t taught much yet, or have only taught comp, prep good syllabuses.
--As you can see, the proposed plan of action is hopelessly contradictory. You need to present yourself as having interests that are both wide-ranging and tightly focused, both innovative and traditional, in all your letters, every time. But hopeless or not, this is the needle any applicant must figure out how to thread; you need to have an application package that will speak to the unknown and unknowable true needs of the departments to which you are applying, whatever they happen to be.
Don’t assume you can know in advance where you will be competitive. There are so many different factors at work in these things that you can’t possibly predict in advance which departments will be interested in you and which won’t. You just have to apply everywhere.
--Networking really helps. My observations of the job market over the last year indicate that the recommendation letter is only the very beginning of the way networking functions in our profession. I would recommend you decide now to be as cynical as possible about this and exploit every advantage you have. With a market as brutal as ours, every little bit helps.
I saw the same thing happening over and over again: people were getting interviews and visits at places where they or their advisers and recommenders had connections. Again, the iron rule: the academic job market is emphatically not a meritocracy.
Keep your advisers, your department's job czar, and other professors in your department up-to-date on your job search, both where you’re applying and where you’re getting dossier requests, interviews, and visits. You never know who might have an unexpected connection someplace that helps grease the wheel.
--On being "elite." People in graduate programs that are perceived to be "elite" definitely still have trouble getting attention from search committee members at "non-elite" institutions and "teaching colleges," who assume either that we won’t actually come, or that we’ll be looking to move on as soon as we get there. In the post-2008-crash job environment, this really isn’t so, if it ever was — but personally I had no success in my attempts to convince anyone of that fact. Generally speaking, these institutions paid no attention to me at all, and I’m not sure what I really could have done differently to get more attention from them than I did. If you are in this situation, I hope you have better luck than I did.
--On being "political." The politics of my work, and of my grad department generally, didn’t seem to be a strike against me, despite my fears about this before the process started — though of course it’s impossible to ever know why you got an interview and why you didn’t. In any event this is more or less already baked into the cake; don’t try to hide who you are.
To this day I have no sense of whether my blog and my Twitter profile helped me or hurt me, much less at what specific institutions they did or didn't. They may have had no effect on my candidacy at all. I do know I spent a lot of time worrying about this for nothing — I can’t recall them even being mentioned at any stage of the search, aside from a very occasional, slightly conspiratorial, "You know, I’ve seen your blog."
--The Academic Jobs Wiki. Opinions differ here, but I found it absolutely indispensable. You need to read the Wiki carefully, and its notes and commentary with a very skeptical eye, but it didn’t seem to me that the information there was notably inaccurate. Given how little information applicants get about the opaque and totally mystified academic job market, combining resources and knowledge seems to me to make a lot of sense, and tends to make the process more, not less, transparent. The Wiki also serves as a very useful archive for when and how decisions have been made in the recent past: I read each year’s page in my subfield going back to before the 2008 crash. Just don’t let it drive you crazy, and don’t let its more paranoid members convince you that every search was written for an inside candidate who is already guaranteed the job. That last part just ain’t so.
--Warning: The process is significantly more expensive than you might anticipate. All told it will probably cost a person between $1,000 and $2,000 to go on the market for the first time. I spent several hundred dollars in postage and dossier send-outs (minimum $6 a pop, commonly $12 or more), including some last-minute FedExing when I didn’t have my act together in time. Some postdocs even have application fees. I had to buy some interview clothes, including new suits, ties, and shirts, as years of being a grad student had left me with nothing acceptably nice; these wound up being a birthday present from my father. My year, the Modern Language Association meeting was in Seattle, which for me meant a costly cross-continental flight and four nights in a hotel at my own expense; luckily, my dad came through again with airline miles to help me out with the flight, and I shared a hotel room with a friend in Seattle. Plan ahead for these expenses where you can.
--Know that you will be unhappy most of the time you’re on the market, but try not to be. I was stressed out continuously from August to February — first just trying to get the applications out, then while waiting for replies, then while prepping for the MLA interview, then while prepping for my campus visits, then for two weeks of waiting after the campus visits while they interviewed the other candidates. It obviously didn't help that I had reached the end of my funding, that I had made the decision not to apply for any new dissertation completion fellowships so as not to split my energy, and that my wife and I had a baby due in April.
Almost all of this stress was completely wasted emotional energy. It's incredibly difficult, but try to remember you can’t actually control any aspect of this very arbitrary process, and that nothing that happens reflects either on the quality of your work or on you personally.
--Lean on each other. A very nice thing about an interdisciplinary graduate department like mine is that generally speaking we’re not all competing for all the same jobs. I know that's not true everywhere — but even if it's not, try to live as if it were. I got a lot of help on my applications from other students in my department, and tried to reciprocate / pay it forward as best I could. Be excellent to each other, if only because the hiring committees won't.
--Really, good luck!
Gerry Canavan is an assistant professor in English department at Marquette University, teaching 20th- and 21st-century literature. He blogs at gerrycanavan.wordpress.com , and tweets @gerrycanavan.