Company galleries can be frustrating, I know!! Once you do one thing, though, you'll be a pro.
Our company galleries are fueled by keywords. So, for High Hopes, you'd enter this in the keyword field when you upload (or click Edit and add the keyword):
highhopes
That will make sure that the gallery finds your card when someone clicks on the High Hopes listing on the Companies page. How do you know what keyword to use? Hover your mouse over a company name, and you'll see the keywords we use there.
It's not hard once you know what to do, and we know it's not all that easy, either. Hopefully that'll change some day soon.