Once a Casting Director has your headshot, unless you're submitting it for a certain role, you wouldn't send a headshot as follow up. Instead, you send a postcard or a note. Remember, there should be a purpose to your follow up; something special, unique, or a question. Just sending postcards every week to say "Hi" isn't as productive as creating a memorable campaign.
Question two, is regarding how many Casting Directors to send to. You want to target the shows you're right for. And when I say "right," I know many actors go into 'chameleon mode' where they can play any role, but if you're 35 and not a character actress, targeting a Disney show isn't as productive as targeting a show that features people your age, weekly.
Because I work with my clients to build strong relationships with people before asking for work, I suggest you start with 20 offices to get well acquainted with and then expand from there.
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