The thing that comes to mind every time I think of artists sending their CVs out is a clip from one of my favorite tv shows, Arrested Development. This clip shows one of Tobias' attempts to nail an acting job...
(I couldn't find the clip so this will have to do)
Tobias Fünke: So fill each one of these bags with some glitter, my photo resume, some candy, and a note.
Mae 'Maebe' Funke: "I know where you live, ha ha!" Casting directors hate this!
Narrator: They really do.
Casting Director: [cut to casting director's office] The glitter queen struck again. Never hire Tobias Funke....
I hope for your sake that you haven't gone to extreme lengths - regardless how "creative" you think you are being. If you're gonna go all out you better make damn sure it blows people out of the water. If this is the case then you probably don't need any of this advice.
TO WHOM IT MAY CONCERN
Sending an Email or Letter?
A Westchester dealer says, "I am not to whom it may concern. If you don't know whom to address, you haven't done your homework."
"Sir or Madam" salutation needs to be retired, too. There's nothing more off-putting than being addressed as "Dear Sir" if you're not a sir. I am a woman, and my name is Dylan. This has happened to me many many times. Good thing I am not in a position where I held the future of your art career in my hands - depending on the morning I'm having I might not be too forgiving.
Sending a Package?
First make sure the gallery is accepting physical packages. Many don't want to deal with the administrative responsibilities and will tell you they prefer electronic submissions.
If the contents peak their interest they will get back to you.
I attended a Studio Visits lecture at the Dallas Contemporary a couple years back. The Director Peter Doroshenko had a lot to say on the matter. He is very proactive and likes that artists take the initiative to send him resumes or packages. But he also said that most galleries and museums like to visit the artist's studio. Even when a collector contacts a museum to donate or loan pieces the curator needs to see the collection before making a decision. Pictures don't always cut it.
When it comes to the pictures you send, in either a package or electronically, make sure the quality of those photos are top notch. These galleries know you are probably poor and struggling to find work, and they expect that, but they also consider this as a job interview. You may not be there personally to hand over your work dressed in a suit or tie, but your packaging or electronic portfolio needs to act as an indication of your professionalism.
Visiting the Gallery? Don't Interrupt
I was talking to this art consultant in New York - we were sitting the gallery proper, and an artist came in with a portfolio. She was hovering even though she was in the background. She was waiting for a break in the conversation, and when it didn't come quickly enough for her, she cleared her throat and said to the dealer, "Hey, I'm here to show my work. Are you the dealer?"
"Did we have an appointment today?"
"No, but you said you'd be willing to look at my work."
"I am willing to look at your work, but you need to make an appointment."
"But I'm here now."
"But I'm busy."
"You're just talking," she persisted, holding her ground.
"Yes, I sure am."
It was literally the most awkward situation I have ever been in, and I wasn't even a part of the conversation. The artist eventually turned her heel and left.
Don't Waste the Dealer's Time
Hundreds of galleries face this issue on a regular basis. Do your homework, peeps. Make sure you know the gallery's name, and again, the gallerist's name. Make sure your work is appropriate or you will be wasting your time as well as the dealer's. Granted, I know its hard to research galleries, especially out-of-state galleries. Their websites are usually minimalistic and vague. That's their appeal.
There is a book I bought a couple years ago when I was still interested in becoming an artist. They come out with annual artist market listings and tips to get your stuff out in the art world. Super useful.
2013 Artist's and Graphic Designer's Market - check it out. It lists almost every known gallery from all over the world. Even the successful small galleries if its the first time showing your work.

