If your worker roles write each finished job's details to a table using a PK of something like (DateTime. MaxValue - DateTime. UtcNow).Ticks.
ToString("d19") you will have a sorted list of the latest jobs that have been processed. Set your web role to poll the table like so.
Depending on upload frequency, you may find queue messages to cause you unneeded updates. For instance, if you get a dozen uploads and process them in close time proximity, you'd now have a dozen queue messages, each telling your web role to update. It would make more sense to keep a single signal (maybe a table row or SQL Azure row).
You could simply set a row value to 1, signaling the need to update. When your web role detects this change, reset to 0 and start the update. Note: If using an Azure Table row, you'd need to poll for updates (and depending on traffic, you could start accumulating a large number of transactions).
You could use the AppFabric Cache for this signal as well.
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