ZenSync tool helps move photos from your computer to Zenfolio. It is run from a command-line and syncronizes your photo collection each time it is run. Zensync goes through an entire directory and uploads only those photos that are not already on Zenfolio. It doesn't matter how you organize your photos -- they just need to be in a single directory tree.
If you were hosting your own photos using Gallery or Coppermine, this would be a great way to transition to Zenfolio.
Dan Richardson is the author of this tool available for download directly from his Web site: www.plymptonia.com
Photo Guru Backup and Restore is a standalone application for Windows. It provides a complete solution for keeping photos on your computer synchronized with a Zenfolio account. You can use this tool to upload photos directly from your PC or download the photos back as you need them.
CMP-Soft is the authoring company of this tool which is available for download directly from their Web site.
Express Send for Zenfolio is an easy to use upload application for Windows.
This handy tool gives you the ability to right-click on any image or folder within Windows and send it directly to your Zenfolio account. Express Send will search through the entire folder structures and upload all the images from the selected folder. Even nested folders will be found and sent. If you store all your images in one directory, right clicking and selecting "Send to Zenfolio" will upload every image from that directory! One click, many uploads.
Text Connects is the author of this tool, which is available for downloading directly from their web site.