Daily Slack digest of stalled Docusign envelopes

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.

Additional information

What does this prompt do?

Scans your Docusign account every weekday morning for envelopes that have been sent but not signed in the last two weeks.
Figures out who has not signed each one and how long it has been since they last opened the document.
Drafts a short, contextual nudge for each stalled deal, gentler at three days and firmer past a week.
Sends every deal owner a single Slack DM that groups all their stalled envelopes together with copy they can send in one click.
For deals older than ten days, can also send the nudge straight to the signer by email when the owner has opted in.

What do I need to use this?

A Docusign account with permission to view envelopes across your team
A connected Slack workspace where deal owners can receive direct messages
Optional: a Gmail account if you want the agent to send follow-ups directly to signers

How can I customize it?

Change the run time or days. The default is 9am Eastern on weekdays, but you can move it to any cadence that fits your team.
Tune the staleness thresholds. The default is a soft nudge at 3 days and a firmer one at 7+ days; bump those up or down to match your sales cycle.
Decide who can email signers directly. Keep it Slack-only for everyone, or let specific reps opt in to having the agent send Gmail follow-ups for envelopes older than ten days.
Adjust the look-back window. Two weeks is a sensible default; shorten it for fast deals or extend it for procurement-heavy contracts.

Frequently asked questions

Will this spam my customers?

No. By default the agent only sends drafts to your reps in Slack. The rep decides whether to send each one. Direct emails to signers only happen if a rep explicitly opts in, and only for envelopes older than ten days.

How is this different from Docusign's built-in reminders?

Docusign's reminders are a fixed cadence with generic copy. This agent reads the audit trail, sees how stale each envelope is, and writes a tailored nudge for that specific deal so the message lands more like a real follow-up than an automated reminder.

Does each rep get one ping per envelope?

No. The agent groups every stalled envelope by deal owner and sends each rep a single digest, so a rep with five stuck deals gets one Slack message, not five.

What if an envelope is already close to closing?

The agent uses the audit trail to see when each signer last viewed the document. Envelopes that are actively being worked on get a softer nudge; ones that have gone fully quiet get a firmer one.

Can I run this for just one team or region?

Yes. You can scope it to a specific Docusign user, group, or folder, or filter to envelopes from certain templates so it only covers the contracts you care about.