Bulk Upload : A Guide for Team Captains

Checkboxes appear on every Checklist Item row on the Checklist, visible only to Team Captains. You can select items individually or use cascade selection to grab an entire Milestone or Checklist Item Group in one click.

Selecting a Milestone selects every eligible Checklist Item under every Group beneath it, including items inside collapsed Groups. Selecting a Group selects every eligible Checklist Item under that Group. Deselecting a parent deselects all of its currently-selected children. The master checkbox in the Checklist header selects or deselects all Checklist Items currently visible under your active filter and search state.

When a parent has some but not all children selected, it displays an indeterminate state [See Below]. When all children are selected, it shows as checked.

📝 Note: Items that are ineligible for document upload (archived items, non-document items) are automatically skipped and surfaced in a separate notice.

Selection state is session-only navigating away or refreshing the page clears it.

When one or more Checklist Items are selected, the Bulk Actions bar replaces the Checklist Item column header. It shows the current count of selected items and a Bulk Actions dropdown.

Select Upload Documents from the dropdown to open the Bulk Upload modal. The modal loads with one row per selected Checklist Item, in the order they appear on the Checklist.

Each row displays the Checklist Item name, an Upload Documents button, a Team Version toggle, and a delete action.

1️⃣ Stage a document for each row

Click Upload to stage a file. Once staged, the cell displays a file icon, hover it to see the filename, or click it to View, Download, or Delete the staged file. Deleting a staged file returns the cell to the Upload button state.

Each committed row creates a new version on its Checklist Item, consistent with the single-document upload flow.

If you're uploading on behalf of the other Team, toggle to their Team name. An Authorized checkbox appears, check it to attest: "I agree and acknowledge that I am acting on behalf of the other Team and that I am authorized to do so."

⚠️ Important: The Authorized checkbox must be checked for every row where you're uploading on behalf of the other Team. It is never pre-checked and is not remembered between sessions. For Checklist Items in Stage 2, 3, or 4, the Team Version toggle is inactive and greyed out, the version is fixed at that stage.

2️⃣ Proceed to the next page

The Next button is enabled only when every row has a staged document and every row that requires the Authorized checkbox has it checked. Hover the disabled button for a reason tooltip.

To remove a row from the modal, click the trash icon. This only removes it from the current bulk upload, it does not deselect the item on the Checklist or modify the Checklist Item itself.

Add an optional comment to provide context. The comment is viewable to all Project users and is attached to every document uploaded in this batch.

⚠️ Important: A cover comment is required to use Upload + Email. It serves as the body of the email sent to the other Team.

Upload (No Email) uploads all staged documents immediately and is always enabled. Upload + Email is enabled only when the cover comment field contains text and advances to Page 3. Back returns you to Page 1 with all staged files and state preserved.

Page 3 presents the same email composition interface as the single-document upload flow, pre-populated with your cover comment as the body, [Project Name] - Documents Updated as the subject line, and all staged documents as attachments.

If the combined attachment payload exceeds 20 MB, all files are packaged into a single .zip before sending. An inline notice confirms when this applies.

Recipients follow the same logic as the single-document Upload + Email flow.

Upload and email are not atomic. dealhead processes them in sequence:

If any individual document upload fails, the modal stays open. Successful rows are committed; failed rows remain with a Retry option. You can retry failed rows without re-entering the cover comment or email.