Zendesk Trial Conversion Campaign

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

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.

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

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

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

Projected metrics

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.