Hi @filipovitz
Can you clarify a bit more?
Do you want to upload the CAD files to ArcGIS Enterprise?
If yes, you should be able to use the ProjectWiseWSGConnector and the ArcGISOnlineConnector transformer to synchronize the CAD files.
If your solution or project workflow involved publishing data to ArcGIS Enterprise.
Technically it is possible but the workflow will be bit involved.
Step 1 Perform CAD TO GIS transformation
There are number of workflow and articles on this topic
How to Convert GIS to CAD while maintaining Data quality
CAD to GIS: Convert Parcel Lines and Text from DGN to Geodatabase
Working with CAD Data
NOTE: you can read file hosted on Projectwise directly using WebAsFileSystem as well.
Step 2 Publish GIS data to ArcGIS Enterprise
This can be achieved by different methods available from ArcGIS Online/Enterprise by by running schedule workspace to perform UPSERT or UPDATE or OVERWRITE.
Using UPSERT/UPDATE using Change Detector
Updating ArcGIS Online Feature Services using UPSERT
In case you want to perform operation such as
CAD → File Geodatabase → ArcGIS Online/ Enterprise
Using Append to Write Big Data to ArcGIS Online in FME
You can do this in a single workflow as well depending on the complication and number of different files and Feature Services that are required.