diff --git a/backend/app/db/models/uploaded_file.py b/backend/app/db/models/uploaded_file.py
index 8decfd1b..71763790 100644
--- a/backend/app/db/models/uploaded_file.py
+++ b/backend/app/db/models/uploaded_file.py
@@ -39,9 +39,21 @@ class UploadedFile(Base):
     hubspot_listing_id = Column(BigInteger, nullable=True)
 
     file_type = Column(
-        SqlEnum(FileTypeEnum, name="file_type", create_type=False), nullable=True
+        SqlEnum(
+            FileTypeEnum,
+            name="file_type",
+            create_type=False,
+            values_callable=lambda enum_cls: [e.value for e in enum_cls],
+        ),
+        nullable=True,
     )
 
     file_source = Column(
-        SqlEnum(FileSourceEnum, name="file_source", create_type=False), nullable=True
+        SqlEnum(
+            FileSourceEnum,
+            name="file_source",
+            create_type=False,
+            values_callable=lambda enum_cls: [e.value for e in enum_cls],
+        ),
+        nullable=True,
     )
diff --git a/backend/ecmk_fetcher/upload.py b/backend/ecmk_fetcher/upload.py
index 00e2ec32..0a744e53 100644
--- a/backend/ecmk_fetcher/upload.py
+++ b/backend/ecmk_fetcher/upload.py
@@ -31,7 +31,9 @@ def upload_file_to_sharepoint(
 def upload_file_to_s3_and_update_db(
     bucket: str, file_path: str, hubspot_listing_id: str, file_type: FileTypeEnum
 ) -> None:
-    key: str = f"documents/hubspot_listing_id/{hubspot_listing_id}"
+    filename: str = os.path.basename(file_path)
+    key: str = f"documents/hubspot_listing_id/{hubspot_listing_id}/{filename}"
+
     upload_file_to_s3(file_path, bucket, key)
 
     uploaded_file = UploadedFile(
@@ -40,7 +42,7 @@ def upload_file_to_s3_and_update_db(
         s3_upload_timestamp=datetime.now(timezone.utc),
         hubspot_listing_id=hubspot_listing_id,
         file_source=FileSourceEnum.ECMK.value,
-        file_type=file_type,
+        file_type=file_type.value,
     )
 
     with db_session() as session: