AI-Generated Emails
How OutSales uses AI to generate personalized follow-up emails based on your CRM data and conversation history.
AI-Generated Emails
OutSales uses AI to create personalized follow-up emails for each of your prospects. Every email is generated using real data from your Pipedrive CRM, previous email conversations, and your Knowledge Base documents.
How Email Generation Works
When a new activity is detected by your agent, the AI generation pipeline begins:
- Data Collection -- OutSales pulls all relevant data from Pipedrive: the deal details (title, value, currency, status), contact information (name, email, company), previous email threads, CRM notes, and organization data.
- Knowledge Enrichment -- If you have uploaded documents to the Knowledge Base, relevant information is retrieved and included as context for the AI.
- Email Generation -- The AI uses all collected data along with your configured prompt to write a personalized follow-up email with an appropriate subject line.
- Quality Check -- The generated email is evaluated for potential issues like banned phrases, generic subject lines, content that is too short, or language mismatches.
What the AI Considers
The email generation prompt receives a rich set of data points:
- Contact details -- The prospect's name, email, and company
- Sender details -- Your name and email address
- Deal context -- Deal title, value, currency, and current status
- Conversation history -- The full email thread with the prospect
- Follow-up count -- How many follow-ups have been sent so far
- CRM notes -- A summary of notes from the deal and contact records
- Closing probability -- The AI-calculated probability score and reasoning
- Organization knowledge -- Relevant information from your uploaded Knowledge Base documents
- Timing data -- Today's date, date of last follow-up, and days since last contact
Quality Warnings
After generation, OutSales checks the email for potential issues. If any are found, a yellow warning bar appears in the Activity Drawer with a quality score out of 100. Possible warnings include:
| Warning | Description |
|---|---|
| Banned phrases | The email contains phrases that should not appear in professional emails |
| Generic subject line | The subject line is too generic and may not grab attention |
| Content too short | The email body is shorter than expected for a follow-up |
| Language mismatch | The detected language does not match the expected language |
These warnings do not prevent you from sending the email -- they are informational flags to help you decide whether to edit or regenerate.
Email Formatting
Generated emails are created in HTML format with proper paragraph structure. When you view them in the Activity Drawer, they appear with full formatting including paragraphs, line breaks, and styling.
When you edit an email, OutSales converts the HTML to plain text for easy editing. Your edits are automatically converted back to properly formatted HTML when you save.
Signatures
Each generated email can include a signature below the body. The signature follows a priority system:
- Custom signature -- If you have set a per-activity custom signature, it appears first.
- Profile signature -- If the agent has "Append Email Signature" enabled and you have configured a signature in your Profile settings, it is used. This can include text and a logo image.
- First name fallback -- If neither of the above is set, your first name from your profile is used as a simple sign-off.
You can override the signature for any individual activity by editing it in the Activity Drawer.
Customizing Generation
You have full control over how emails are generated:
- Custom prompts -- Edit the system prompt and user template in the agent's Settings tab to control the AI's writing style, tone, and structure. See Custom Prompts.
- Knowledge Base -- Upload company documents, product information, or sales materials that the AI will reference when writing emails. See the Knowledge Base section in Settings.
- Model selection -- Choose between GPT-4o Mini (faster) and GPT-4o (more accurate) depending on your quality and speed preferences.
- Temperature -- Adjust the creativity slider to control how varied the AI output is.
Tips
- Review a sample first -- Before enabling automatic sending, review a batch of AI-generated emails with the approval flow to calibrate quality.
- Upload relevant documents -- The more context the AI has from your Knowledge Base, the more specific and relevant the generated emails will be.
- Watch the quality scores -- Pay attention to quality warnings and consider adjusting your prompts if warnings appear frequently.