Re-engage stalled HubSpot deals with GPT-5-mini, Gmail, and Slack

Who is this for

This workflow is designed for Customer Success Managers and Sales Teams who manage high-volume pipelines in HubSpot. If you have prospects who stop responding after the contract is sent, this automation helps you recover them without manual follow-up.

What it does

This template automatically identifies deals that have "stalled" in your pipeline (specifically in the Contract Sent stage) and initiates a personalized re-engagement sequence.

1. Monitors Pipeline: Runs on a schedule to find deals marked as stalled in HubSpot.
2. Smart Filtering: Identifies all associated contacts for a deal and selects the first available contact. This ensures the email goes to a real person involved in the deal.
3. Spam Prevention: Fetches the Last Contacted date from HubSpot. If there has been any activity (call, email, meeting) in the last 7 days, the workflow skips that contact. This safety gate prevents automation from interfering with active conversations.
4. AI Personalization: Uses GPT-5-mini (via OpenAI) to generate a helpful check-in email. The prompt is context-aware, using the contact's name and deal stage to sound personal rather than generic.
5. Multi-Channel Sync: Sends the approved email via Gmail, alerts the internal team in Slack, and logs the email body to the HubSpot Activity Timeline.

How to set up

1. Credentials: Connect your HubSpot, OpenAI, Slack, and Gmail accounts in n8n.
2. Configuration: Open the Config: Setup Variables node and enter your Sender Name, Company Name, and Calendar Link.
3. Slack Channel: Open the Slack: Notify CSM node and select the channel where you want your team to be alerted (e.g., #sales-alerts).
4. HubSpot Settings: By default, this targets the contractsent stage. Ensure your HubSpot pipeline matches this ID.

Requirements

• n8n (Cloud or Self-hosted)
• HubSpot account
• OpenAI API Key
• Gmail & Slack accounts

How to customize the workflow

• Target Different Stages: To re-engage leads in other phases (e.g., "Qualification" or "Onboarding"), open the HubSpot: Search Stalled Deals node and change the dealstage filter to your desired pipeline stage ID.
• Adjust the Safety Gate: The workflow blocks emails if there has been contact in the last 7 days. To change this window (e.g., to 30 days for cold leads), open the Filter: Last Activity Check node and edit the time value in the expression.
• Modify the AI Persona: Open the AI: Generate Email node to edit the System Prompt. You can adjust the tone (formal vs. casual), lengths constraints, or language to match your brand voice.