Reported, not yet confirmed.
File weekly NDAs from Gmail into HubSpot and Drive
Sunnyvale's ChatGPT scheduled prompt finds executed NDAs in mail and reconciles them to the CRM company and the customer folder.
Sunnyvale shows a weekly ChatGPT scheduled prompt that searches Gmail for executed NDAs and MNDAs, then files each one on the HubSpot company record and in the matching Google Drive customer folder when it is missing. The opener says the example "runs on my ChatGPT account weekly." The claim is self-reported. We have not run it.
What it replaces#
Before: a person digs through the inbox for signed NDAs, opens HubSpot, opens Drive, and uploads by hand while trying not to double-file. After: one scheduled sweep re-reads live Gmail, HubSpot, and Drive, adds only what is missing, and leaves a short exceptions list for anything it cannot match with confidence.
Sunnyvale says the same pattern also covers insurance requirements in contracts, subprocessor legal notifications, HR paperwork filing, and customer contract filing.
How it works#
Sunnyvale's build pattern is four steps: ask the AI to write the prompt, review it, test it, then schedule it. The article says the example should take less than five minutes to build.
- Ask ChatGPT to draft the weekly sweep in plain language (starter below).
- Review the returned prompt. Keep the rules that drafts and redlines are not executed agreements, that ambiguous companies or folders become exceptions, and that the job never deletes or overwrites an existing agreement.
- Test on three cases: an executed NDA already in both places (no write), one missing from HubSpot only, and one with an ambiguous company name (exception, no attach).
- Schedule it weekly. Treat every run as stateless: re-derive state from the live systems, with a rolling 21-day Gmail lookback so prior finds may reappear and duplicate detection stays mandatory.
Our starter, adapted from the author's request (not their exact words):
Write me a prompt for a weekly scheduled sweep of my email box.
Look for NDA and MNDA agreements. Then look in HubSpot for the company
object and the customer folder, and find if the NDA is already there.
If it is not in either place, add it to both. Do not create duplicates.
The published prompt then requires: search broadly (NDA, MNDA, Non-Disclosure Agreement, Mutual NDA, Confidentiality Agreement, and close variants); inspect attachments, not only subjects; prioritize fully signed, DocuSign or Adobe Sign completed, or otherwise final PDFs; identify the counterparty from the agreement first; never create a HubSpot company; never guess a Drive folder from a similar name; compare more than filenames for duplicates; and finish with a reconciliation report (added to both, HubSpot only, Drive only, already reconciled, exceptions, totals).
What you need connected#
A ChatGPT account with Gmail, HubSpot, and Google Drive connected, per the author's article. HubSpot COMPANY records should already exist for the counterparties you care about. Prefer an explicit Drive customer-folder link on the HubSpot company record so the job does not guess folders by name.
Good to know#
- This is a filing job, not a legal review. It does not decide whether an NDA is a good deal. It only moves executed copies into the two systems of record when confidence is high.
- Ambiguous companies, missing folders, and version conflicts stay as exceptions. The published safety rules forbid attaching to an uncertain company, uploading to an uncertain folder, deleting, overwriting, or treating an unsigned draft as executed without evidence.
- Sunnyvale notes a possible next step: log every action to a Google Sheet, which they already use on most of their other scheduled actions.
- We did not reproduce the run on this box.
Same idea in Grok Bot#
Grok Bot can run the same weekly pass as a scheduled routine on one Bot, with the method saved as a skill first. Gmail and Google Workspace plugins cover mail and Drive. HubSpot is in the GTM connector set announced Sep 10. Keep create-company and delete actions off; this workflow is meant to attach and upload, not invent CRM records. Leave ambiguous matches for you.
