Trial-to-Paid Conversion

Define trial success criteria in a spreadsheet: 3-5 activation milestones that predict paid conversion (e.g., completed setup, invited team, used core feature 3x, integrated with tool, achieved first outcome).

Track 10 active trial users in Attio; for each, monitor which activation milestones they hit and when; identify patterns in users who convert vs those who don't.

Set pass threshold: >=40% of trial users convert to paid within trial period (typically 14 days), and users who hit >=3 activation milestones convert at >=2x rate vs users who hit <3.

Send manual check-in emails at days 3, 7, and 12 of trial: offer help, share tips for hitting activation milestones, schedule calls with users stuck on setup.

For users who hit activation milestones, send success confirmation: "Congrats on [milestone]! You're getting great value—here's what to try next." For users who don't, send targeted help: "Noticed you haven't [action]—here's a 2-minute guide."

Log trial activity in PostHog: track trial_started, activation_milestone_hit, trial_engaged, trial_converted, trial_expired events with properties for milestone completion and engagement level.

Call high-intent trial users (hit >=2 milestones) at day 10 to discuss upgrade: "You've been getting great results—let's talk about moving to paid so you can [unlock benefit]."

Create urgency as trial end approaches: "Your trial expires in 2 days—upgrade now to keep your data and momentum" with clear upgrade CTA.

After 1-2 weeks, analyze conversion rate overall and by activation milestone completion; if >=40% convert and milestone completion predicts conversion, you have a working trial-to-paid motion.

If threshold met, document activation milestones and touchpoint cadence, then proceed to Baseline; otherwise refine activation criteria or improve trial experience.