How to Automate Email Workflows from Your CRM
How to Automate Email Workflows from Your CRM
The Email Bottleneck
Your SDRs spend 3-4 hours every day on email: pulling prospect data from HubSpot, researching the company, drafting personalized messages, copying everything into Gmail, and logging the activity back to the CRM. By the time they finish 20 emails, half the workday is gone.
The math is brutal: if each email takes 10 minutes to research, write, and send, an SDR can only contact 48 prospects per day. Meanwhile, competitors with better automation are reaching 200+ prospects with the same team size.
Your reps aren't slow—your process is manual. Every copy-paste between HubSpot and Gmail is wasted time. Every "let me pull up their company info" is friction. Every "did I log that email?" is lost data.
The Solution: Automated Email Workflows
Build email automation that generates personalized messages from your CRM data and creates ready-to-send Gmail drafts. With Replit Agent, HubSpot, and Gmail Connectors, automate outreach while maintaining quality.
What You'll Build
- Context-aware email generation using CRM data like company, title, recent activity, and pain points
- One-click Gmail integration that opens pre-filled compose windows ready to send
- Template library for different scenarios: cold outreach, demo follow-up, contract renewal, etc.
- Personalization tokens automatically filled from HubSpot properties
- Activity logging back to HubSpot so every email is tracked
Watch the Full Tutorial
See this automation built live in our webinar, where we create an end-to-end email workflow that goes from CRM contact to Gmail draft in seconds.
Key timestamps:
- 28:32–29:23: Email generation and personalization setup
- 29:40–30:22: Gmail integration and one-click draft creation
How It Works: Step-by-Step
Step 1: Connect Gmail and HubSpot
Use Replit's pre-built Connectors to authenticate both platforms. No API key management, no OAuth configuration headaches—just click to connect and you're ready.
Step 2: Define Your Email Templates
Create templates for different outreach scenarios. Example prompt to Agent:
"Build an email template for cold outreach to director-level prospects at companies with 100-500 employees. The email should reference their company name, their role, mention a pain point relevant to their industry, introduce our solution briefly, and request a 15-minute call. Keep it under 150 words."
Agent creates the template structure with placeholders for dynamic content.
Step 3: Set Up Personalization Logic
Tell Agent what data to pull for each email:
"For each contact, get: company name, contact's full name and title, company size and industry, any recent activity (website visits, email opens, content downloads), notes from previous conversations, and deal stage if they're in an opportunity."
Agent builds the data fetching logic that pulls this context before generating each email.
Step 4: Create Your One-Click Interface
Build a simple interface:
"Create a button next to each contact in my list labeled 'Generate Email.' When clicked, fetch the contact data, generate a personalized email using the appropriate template based on their deal stage, and open a Gmail draft addressed to them with the email pre-filled and ready to review."
Now your reps have a one-button solution: find a prospect, click, review the generated email, and send.
Step 5: Log Activity Back to HubSpot
Close the loop:
"After an email draft is created, immediately log an email activity to the contact's timeline in HubSpot with the subject line and a note that it was auto-generated. When the rep sends the email from Gmail, update the activity to 'Sent' with the timestamp."
Your CRM stays perfectly updated without any manual logging.
Personalization Best Practices
Level 1 - Basic: Name, company, title
"Hi {{firstName}}, I noticed you're the {{title}} at {{companyName}}..."
Level 2 - Firmographic: Add company size, industry, location
"As a {{employeeCount}} person {{industry}} company in {{city}}, you're probably dealing with..."
Level 3 - Behavioral: Reference recent activity
"I saw you downloaded our guide on {{contentTopic}} and visited our pricing page..."
Level 4 - Contextual: Use news, funding, hiring signals
"Congrats on the Series B announcement last week. With your expansion into {{newMarket}}, you might be interested in..."
Level 5 - Relationship: Mention mutual connections or past interactions
"{{mutualConnection}} mentioned you're looking for solutions to {{specificPainPoint}}. When we spoke at {{eventName}} last month..."
Higher levels require more data but generate better response rates. Start with Level 2-3 and add complexity as you gather more signals.
Email Generation Logic
Replit Agent generates emails by pulling contact data, company information, and recent activity from HubSpot. It selects the appropriate template, fills personalization tokens, and creates a Gmail draft for review. The system flags any missing personalization data before presenting the email.
Advanced Capabilities
A/B Testing: Generate two variants of each email. Track which versions get better response rates. Automatically optimize templates over time.
Send-Time Optimization: Analyze when each prospect typically opens emails. Schedule sends for their highest-engagement window.
Multi-Channel Sequences: Combine email with LinkedIn messages and phone calls. Generate cadences across channels.
Reply Detection: When a prospect replies, automatically pause the sequence, notify the rep, and suggest next steps based on sentiment analysis.
Signature Automation: Use each rep's personal Gmail signature automatically. Maintain brand consistency while keeping personal touches.
Metrics to Track
Track key metrics: response rate by template, time saved per email, and personalization success rate. Monitor manual edit frequency—high rates indicate templates need improvement.
Get Started with Email Automation
Build automated email workflows that generate personalized outreach in seconds.
See how to build the complete workflow from CRM trigger to Gmail draft, with real emails being generated and sent.
Common Questions
Can I review emails before they send?
Yes. The default workflow creates Gmail drafts for review. You can also configure fully automated sending for specific scenarios.
What if personalization data is missing?
You set fallback rules. Use generic language, flag for manual review, or skip that email entirely.
Can I use my own email templates?
Yes. Import existing templates and Agent will adapt them to work with dynamic personalization.
Does this work with Outlook?
Not yet, but Outlook connector support is in development. The same concepts apply.
How do I prevent emails from sounding robotic?
Use AI to generate, but keep templates conversational. The best approach is AI-assisted, human-reviewed.
Can I A/B test subject lines?
Yes. Generate multiple variants and track performance. Agent can auto-optimize based on results.
Is there a sending limit?
Gmail's standard limits apply (500/day for Google Workspace). Use multiple sending addresses or email infrastructure for higher volume.
Start Building Today
Your reps should be talking to prospects, not copying data between systems. Build email automation that scales your outreach while maintaining quality.
Build email workflows that generate personalized outreach using your CRM data and create ready-to-send Gmail drafts in seconds. Connect HubSpot and Gmail to eliminate manual copy-paste and scale high-quality outbound.
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