Daily nudge for stalled Docusign envelopes

By General Input

Every weekday at 9am ET, find Docusign envelopes that have gone quiet and send each deal owner a Slack digest with ready-to-send follow-up notes.

Integrations

  • Docusign
  • Slack
  • Gmail

Type

Agentic Task

Categories

  • Sales
  • Operations

Build me an agent workflow that chases down stalled Docusign envelopes every weekday morning so deals don't die in someone's inbox.

Trigger: cron, every weekday (Monday through Friday) at 9:00am America/New_York.

What the agent should do on each run:

1. Call Docusign List Envelopes filtered to status 'sent' or 'delivered' with from_date set to roughly 14 days ago, so I get the active envelopes that have not yet been signed or completed.

2. For each envelope returned, call Docusign Get Envelope, List Recipients, and Get Envelope Audit Events to figure out: which signer(s) have not yet signed, when each non-signed recipient last viewed the document (if ever), how many days ago the envelope was sent, and who the envelope owner / sender is.

3. Decide which envelopes count as 'stalled' and bucket them by staleness. A reasonable default: 3+ days since sent or last view = soft nudge, 7+ days = firm nudge, 10+ days = candidate for direct email to the signer if the owner has opted in. Skip envelopes that are clearly progressing (e.g. another signer in the routing order just signed today).

4. For every stalled envelope, draft a short, specific follow-up note tailored to: the contract type (use the envelope subject / template name as a hint), how stale it is, and which signer is the blocker. Tone should be gentle at 3 days and progressively firmer past a week. Keep each draft to 2-4 sentences and write it in the owner's voice as if they were sending it themselves.

5. Group the stalled envelopes by envelope owner. For each owner, post one Slack Send a Message to that owner's DM containing a single digest: a short summary line ('You have 4 stalled envelopes'), then for each envelope a block with the counterparty name, contract title, days stalled, who is blocking, the drafted nudge in a code block (so it's one-click copyable), and a Docusign link. One Slack message per owner, not one per envelope.

6. For envelopes 10+ days stale where the owner has opted in (treat this as a configurable list of owner emails for now), the agent should additionally call Gmail Send a Message to the blocking signer with the drafted nudge, sent from the owner's Gmail account. Include the owner on the message so they have a record. Note this in the Slack digest so the rep knows the email already went out.

Resolving owner -> Slack DM: look up the Slack user by the envelope sender's email. If no Slack user matches, skip Slack for that owner and log it. Resolving owner -> Gmail account: only the owner's own Gmail connection should be used to send to signers; if it's not connected, skip the email step for that owner.

Edge cases to handle: envelopes with multiple unsigned recipients (mention all blockers), envelopes that have been voided or completed since the list call (re-check Get Envelope before drafting), envelopes where the owner has no stalled deals today (don't send an empty digest), and rate limiting on Docusign (paginate List Envelopes if needed). If there are zero stalled envelopes across the org, do nothing.

Make the staleness thresholds (3 / 7 / 10 days), the lookback window (14 days), the run time, and the list of owners opted in for direct email easy to edit at the top of the agent's instructions so I can tune them later.

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