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Send CRM lead outreach emails with Notion, Gmail, Google Drive and OpenAI

by Marc Soummeradapted from n8n official workflow galleryUpdated Aug 2026
RequiresCCodeGmailGmailGoogle DriveGoogle DriveNotionNotionOpenAITwilioTwilio
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When CRM Lead Added to NotionWhen CRM Lead A…IfCheck Valid Email FormatCheck Valid Ema…IfIf Previously EmailedIf Previously E…Send Personalized Email via GmailSend Personaliz…Update Notion for Emailed LeadUpdate Notion f…Fetch Sent Mail from AccountFetch Sent Mail…Download Specs PDF from Google DriveDownload Specs …Download Proposal PDF from DriveDownload Propos…CoConvert to Attachment BinariesConvert to Atta…MeMerge Attachment PDFsMerge Attachmen…Fetch Sent Mail from Account 3Fetch Sent Mail…IfDetermine Contact NameDetermine Conta…Send Generic Email via GmailSend Generic Em…WaWait for Bounce NotificationWait for Bounce…Fetch Bounce Emails in GmailFetch Bounce Em…IfIf Bounce DetectedIf Bounce Detec…Update Notion for Invalid EmailUpdate Notion f…IfProcess Already Emailed LeadProcess Already…Update Notion for Already EmailedUpdate Notion f…IfIf Can Update Lead StatusIf Can Update L…MeMerge Sent Emails ResultsMerge Sent Emai…CoFlag as Previously EmailedFlag as Previou…WaWait 7 SecondsIfCheck Draft Review DomainCheck Draft Rev…Create Gmail Draft for ApprovalCreate Gmail Dr…Notify Rep via TwilioNotify Rep via …When Gmail Bounce DetectedWhen Gmail Boun…IfIf Bounce Notification ExistsIf Bounce Notif…Extract Bounced Email AddressExtract Bounced…Fetch All CRM LeadsFetch All CRM L…Update Notion for Bounced LeadUpdate Notion f…IfFind Matching Bounced LeadFind Matching B…12345678910111213141516171819202122232425262728
1/5
FLOWS
STEPS · 28
Starts on a Notion event

Quick Overview This workflow watches a Notion CRM for leads ready to contact, checks Gmail to avoid duplicate outreach, then sends or drafts an email with Google Drive PDF attachments and updates the lead status in Notion, with bounce detection that marks invalid emails (using OpenAI to extract addresses). How it works Triggers when a lead page is updated in a selected Notion CRM database. Validates that the lead’s Email field looks like an email address and searches Gmail Sent for recent messages to that recipient to detect prior outreach. If the lead was already emailed and the current status is safe to overwrite, it updates the Notion lead status to “Emailed.” If the lead was not previously emailed, it downloads two PDF attachments from Google Drive, converts them to Gmail attachments, and either creates a Gmail draft for specific domains (optionally sending a Twilio SMS to a rep) or sends a generic vs personalized Gmail email based on whether a contact name exists.

Tags

n8nreference-onlygmailgoogle-drivenotionopen-aitwilio
Connects
CCodegmailGmailgoogledriveGoogle DrivenotionNotionOpenAItwilioTwilio
CategoryAI Automation
Triggermanual
Complexityadvanced
Nodes32
AddedJul 18, 2026

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