Hey apspencer!
I just checked myfonts cause i have a webfont there too.
When im using the "webfont kit builder" then I'm getting these files:
Screen Shot 2016-09-14 at 08.56.58.png
I then rename the .woff file to myfont.woff cause lay theme doesnt support fontfiles that start with a number in their filename.
Then I upload the font and it works.
If you are doing the same and it does not work for you, please send me your webfontkit to armin.unruh@gmail.com along with a link to this topic