Pipedrive Email Automation:
Sequences That Actually Convert

How Pipedrive Email Automation Works

Pipedrive offers two levels of email automation:

• Workflow Automations (built-in): Trigger emails when deal events happen — stage changes, deal creation, activity completion. Available on Advanced plan ($28/user/mo) and above.
• Campaigns by Pipedrive: Pipedrive's email marketing add-on for bulk email campaigns, newsletters, and drip sequences to segmented lists. Starts at $13/mo for up to 1,000 contacts.

For most sales teams, workflow automations handle the heavy lifting. Campaigns is useful for marketing-style email blasts.

5 Email Sequences Every Pipedrive User Needs

1. New Lead Welcome Sequence (3 emails)

Trigger: New deal created from web form

• Email 1 (Immediate): "Thanks for reaching out! Here's what happens next..." — Sets expectations, provides booking link, establishes credibility with a brief case study mention.
• Email 2 (Day 2): Value-first email — share a relevant resource (guide, checklist, video) that helps the lead even if they never buy.
• Email 3 (Day 5): Social proof email — "Here's how [similar company] solved the exact problem you have" + CTA to book a call.

2. Post-Demo Follow-Up (4 emails)

Trigger: Deal moves to "Demo Completed" stage

• Email 1 (Same day): Recap of the demo — key points discussed, answers to their questions, recording link.
• Email 2 (Day 2): Send proposal/pricing — keep it clean and simple.
• Email 3 (Day 5): Objection-handling email — address the top 3 concerns prospects have after demos.
• Email 4 (Day 10): Soft deadline — "I want to make sure I'm not wasting your time. Shall I close this out or is there something I can help with?"

3. Proposal Follow-Up (3 emails)

Trigger: Deal moves to "Proposal Sent"

• Email 1 (Day 3): "Just checking in — any questions about the proposal?"
• Email 2 (Day 7): Add urgency — limited-time pricing, upcoming availability changes, or a bonus.
• Email 3 (Day 14): Final follow-up — "I'll close this out on my end, but happy to revisit anytime."

4. Lost Deal Re-Engagement (3 emails)

Trigger: Deal marked as Lost

• Email 1 (Day 30): "No hard feelings — here's a free resource that might help."
• Email 2 (Day 60): Share a relevant case study from a similar company.
• Email 3 (Day 90): "Things change — are you still happy with your current solution?"

5. Customer Upsell/Cross-Sell (2 emails)

Trigger: 90 days after deal won

• Email 1 (Day 90): Check-in — "How's everything going?" + satisfaction survey.
• Email 2 (Day 100): Introduce complementary service or upgrade option.

Pipedrive Email Automation Best Practices

Write Like a Human, Not a Robot

The best automated emails don't feel automated. Use the prospect's first name, reference their company, and write in a conversational tone. Short paragraphs. No corporate jargon.

Use Plain Text (Mostly)

HTML-heavy emails with images and buttons scream "marketing email" and get lower reply rates. For sales sequences, use plain text with a simple signature. Save the fancy designs for newsletters.

Set Proper Stop Conditions

Stop the sequence when the prospect replies, books a meeting, or the deal moves to the next stage. Nothing kills trust faster than getting an automated follow-up after you've already replied.

Space Your Emails Properly

Don't send 3 emails in 3 days. Space them out: Day 0, Day 3, Day 7, Day 14. Give prospects time to read, think, and respond.

Track and Optimize

Monitor open rates (aim for 50%+), reply rates (aim for 10%+), and meeting booked rates. If Email 2 has a 5% open rate, the subject line needs work. If Email 3 gets replies but not meetings, the CTA needs work.

Pipedrive Email Templates That Convert

Sequence Type	Avg Open Rate	Avg Reply Rate	Key Success Factor
Welcome / New Lead	65-80%	15-25%	Speed (send within 1 min)
Post-Demo Follow-Up	55-70%	20-30%	Personalized recap
Proposal Follow-Up	50-65%	10-20%	Adding urgency
Lost Deal Re-Engagement	30-45%	5-10%	Value-first approach
Customer Upsell	45-60%	10-15%	Timing (after success)