Transaction based monitoring service for rails

I am looking for a service for my rails application to monitor and alert/notify based on transaction based tests. I already looked at pingdom but it doesn't support uploading files and that's crucial to my use case. what other services i can use to test and monitor my transaction. My use case is as follows:

1. User logs in to their iTunesConnect account via our login form
2. User selects multiple image(s) to upload to iTunesConnect
3. The images get uploaded locally
4. User see the preview screen to preview the images and pass validations
5. Final upload which is through a background service where the images get uploaded to users' iTunesConnect account.