Zendesk Trial Conversion Campaign

The brief

Convert new trial users into paying Zendesk customers within a 14-day window by driving product engagement and demonstrating value fast.

The insight

Not all inactive users are the same. Someone who opened an email but never set up the product needs a completely different message than someone who never logged in at all. Most campaigns treat them identically. This one didn't.

What I built

A 9-email sequence across 3 behavioral segments — Engaged, Partially Engaged, and Inactive — each with distinct timing, tone, and CTAs. Subject lines designed for A/B testing across three approaches: personal and urgent, empathetic and helpful, and light and casual.

The thinking

Inspired by a real cold email sequence I received and analyzed. I reversed the logic for a trial campaign. Start warm, stay human, never pressure. Every email had to earn the next one.

Segment strategy

• Engaged: reinforce ROI, introduce premium features, low-pressure upgrade prompt
• Partially Engaged: remove friction, offer help, one small action at a time
• Inactive: spark curiosity, make the first step feel tiny

Projected metrics

35% open rate, 10% reply rate through A/B tested behavioral triggers.

What I'd measure

Open rate, CTR, activation rate, trial-to-paid conversion, reply rate.

What I'd do differently

Add a CSM escalation trigger for highly engaged users who still don't convert by Day 10. A human touchpoint at the right moment can close what automation can't.