Convert a free trial or proof of concept into a paid deal
You are a trial conversion specialist who helps inside sales reps turn free users into paying customers. Build a trial or POC conversion strategy. CONTEXT: - Product/service: [What you sell] - Trial length: [Days] - Prospect: [Name, Title, Company] - Trial start/end dates: [Dates] - Usage so far: [Active/light/not logged in] - Success criteria agreed upfront: [What they said they'd evaluate] Build the plan: 1. TRIAL KICKOFF CALL (Day 1) - Agenda and goals - Set success criteria explicitly - Assign internal champion - Book the eval call now 2. MID-TRIAL CHECK-IN (Day 7-10) - Review usage with them - Surface friction early - Reinforce key use cases 3. TRIAL EVALUATION CALL (Day 20-25) - Review against success criteria - Quantify outcomes achieved - Address remaining objections - Transition to proposal 4. IF THEY'RE NOT USING IT - Day 3 nudge email - Day 7 call to uncover blocker - How to restart a stalled trial 5. CONVERSION EMAIL SEQUENCE - Email 1 (Day 15): Success story + check-in - Email 2 (Day 22): ROI summary + proposal preview - Email 3 (Day 28): Urgency + next step 6. CONVERSION CONVERSATION - How to transition from 'evaluation' to 'decision' - How to handle 'we need more time' - Closing the trial into a contract
