I know I'm missing something in the details here.
Despite Googling, trying examples, different formats, etc, the AJAX request that I send always is validated as having all fields empty, but not being null.
I think I'm not sending things in the proper format for the controller to recognize it as an object but I'm not sure what.
With some dummy data:

public class ContactUsMessage
{
    public string Email { get; set; }
    public string Name { get; set; }
    public string PhoneNumber { get; set; }
    public string Message { get; set; }
}
    [HttpPost]
    public HttpResponseMessage NewMessage(ContactUsMessage messageToSend)
    {
        if (messageToSend == null)
        {
            var sadResponse = Request.CreateResponse(HttpStatusCode.BadRequest, "Empty Request");
            return sadResponse;
        }
        var messageValidator = new ContactUsMessageValidator();
        var results = messageValidator.Validate(messageToSend);
        var failures = results.Errors;
        var sadString = "";
        if (!results.IsValid)
        {
            foreach (var error in failures)
            {
                sadString += " Problem: " + error.ErrorMessage;
            }
            var sadResponse = Request.CreateResponse(HttpStatusCode.NotAcceptable, "Model is invalid." + sadString);
            return sadResponse;
        }
        else
        {
            SendContactFormEmail(messageToSend.Email, messageToSend.Name, messageToSend.PhoneNumber, messageToSend.Message);
        }
function sendSubmissionForm() {
    var dataObject = JSON.stringify(
        {
            messageToSend: {
                'Email': $('#inpEmail').val(),
                'Name': $('#inpName').val(),
                'PhoneNumber': $('#inpPhone').val(),
                'Message': $('#inpMessage').val()
            }
        });
    $.ajax({
        url: '/api/contactus/newmessage',
        type: 'POST',
        done: submissionSucceeded,
        fail: submissionFailed,
        data: dataObject
    });
}
                When you JSON.stringifyied your data object you converted it to JSON. But you forgot to set the Content-Type request header and the Web API has no way of knowing whether you are sending JSON, XML or something else:
$.ajax({
    url: '/api/contactus/newmessage',
    type: 'POST',
    contentType: 'application/json',
    done: submissionSucceeded,
    fail: submissionFailed,
    data: dataObject
});
Also when building the JSON you don't need to wrap it in an additional property that matches your method argument name. The following should work as well:
var dataObject = JSON.stringify({
    'Email': $('#inpEmail').val(),
    'Name': $('#inpName').val(),
    'PhoneNumber': $('#inpPhone').val(),
    'Message': $('#inpMessage').val()
});
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