The Proactive Chat Playbook: Message Visitors Before They Ask

Proactive chat — starting a conversation with a visitor before they message you — sounds intrusive. Done wrong, it is. Done right, it converts at 3x the rate of reactive support and catches problems before they become complaints.

The golden rule of proactive chat

Only trigger a proactive message when you have something genuinely useful to say, based on what the visitor is doing.

Bad: "Hi! Can I help you with anything today?" (on every page, immediately)

Good: "I noticed you've been on our pricing page for a few minutes — happy to answer any questions about which plan fits your team." (on /pricing, after 90 seconds)

The second message works because it's contextual and specific. The visitor knows you're paying attention, not running a script.

The 7 highest-converting proactive triggers

1. Pricing page dwellers

Trigger: Time on /pricing > 90 seconds

Message: "Still deciding on a plan? I'm happy to help you figure out which one fits your team size and budget."

Why it works: Anyone spending 90 seconds on a pricing page has a purchase intent question. Meeting them there closes deals.

2. Checkout abandonment

Trigger: Time on /checkout > 60 seconds without submitting

Message: "Looks like you might have a question before checking out. Any hesitations I can help with — shipping, returns, sizing?"

3. Repeat visitors (3+ sessions) who haven't converted

Trigger: Visit count ≥ 3, not a customer

Message: "Welcome back! You've visited a few times — is there anything holding you back that I can help clarify?"

4. Feature page for paid features

Trigger: Free-plan user lands on a paid feature page

Message: "This feature is available on the Pro plan. Want me to show you what else is included?"

5. Error page visitors

Trigger: URL contains /error or /404

Message: "Looks like something went wrong. Let me know what you were trying to do and I'll help you get there."

6. Long session, no action

Trigger: 10+ minutes on site, no form submission or purchase

Message: "You've been exploring for a while — finding everything okay? Happy to give you a quick tour of [relevant feature]."

7. Return from email campaign

Trigger: UTM source = email campaign

Message: "Welcome back! You came from our [campaign] email — anything from that I can help you with?"

Setting these up in Kerabie

Go to Campaigns → New campaign → Proactive message and set:

• Trigger type (page visit, time on page, visit count)
• Conditions (URL match, user attributes)
• Message text
• Delay (never trigger immediately — minimum 30 seconds)

A/B test your messages. The difference between a 2% and 8% engagement rate is usually the message copy, not the trigger.

Set up proactive campaigns →