Hi Sam,
Thank you for your question! At this time, you are only able to post one On-Demand Video to a single session, as the functionality is truly to be a recording of the session. If you'd like to host multiple On-Demand videos, we recommend our Events+ option which is a library of curated content that your attendees can browse through. You can find more information at the link below and if you'd like a demo of this product, you can always reach out to your Account Manager who can help coordinate this!
https://support.cvent.com/s/communityarticle/Setting-Up-a-Video-Center?is_article=true&lang=en_US&searchFor=events%20&page=1
Thank you!
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Erica Kennedy
Senior Client Success Manager
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