Convert more trials by reaching out at the perfect moment. This workflow monitors trial user behavior in Segment, uses AI to identify buying signals and engagement patterns, and sends instant Slack alerts when users show high intent so your team can offer help before the trial ends.
Receive user event from Segment
The workflow triggers when trial users complete significant actions tracked in Segment. It captures the event details along with the user's full activity history, company information, and trial timeline to provide context for analysis.
Analyze user behavior patterns with OpenAI
Using OpenAI, the workflow analyzes the user's behavior patterns to calculate a conversion likelihood score. The AI looks for buying signals like pricing page visits, team invites, integration setup, power feature usage, and high engagement velocity. It also flags churn risks like declining activity.
Generate personalized outreach suggestions
For high-intent users, the AI generates personalized outreach suggestions based on their usage patterns. It identifies which features they're getting value from, what they might be struggling with, and suggests relevant case studies or resources to share in the conversation.
Send conversion alert to Slack
An alert is sent to Slack with the user details, conversion score, key buying signals observed, personalized outreach suggestions, and days remaining in trial. Sales can immediately reach out with relevant, helpful context instead of generic check-in messages.
Why automate trial conversion signals?
Timing is everything in trial conversion. Reach out too early and you're pushy. Too late and they've already decided. AI-powered signal detection tells you exactly when users are ready for a conversation.
Reach out when users are most receptive
Users who just hit an aha moment are primed to talk about upgrading. The workflow catches these moments in real-time so you can strike while the iron is hot instead of following up on arbitrary schedules.
Focus sales time on high-intent trials
Not every trial deserves the same attention. With conversion scoring, your team focuses on users showing real buying signals instead of spreading thin across every trial. Work smarter, not harder.
Personalize outreach with usage context
Generic "How's your trial going?" emails get ignored. When you know exactly which features a user loves and what they're trying to accomplish, you can offer genuinely helpful guidance that builds trust and drives conversion.
How to set up trial conversion alerts
Setting up this trial monitoring workflow takes about 20 minutes. You'll configure your event tracking, define buying signals, and set up alert routing.
What you need to get started
- Segment account tracking trial user events
- Key events defined (activation, feature usage, etc.)
- OpenAI API key for behavior analysis
- Slack workspace for sales alerts
Defining your buying signals
- Identify actions that correlate with conversion (pricing page views, team invites, etc.)
- Define your activation milestone events
- Set thresholds for engagement velocity (actions per day/week)
- Identify features that indicate serious evaluation
- Configure churn risk signals (declining activity, support tickets)
Configuring alert routing
- Set conversion score thresholds for different alert types
- Route enterprise trials to different channels
- Configure alert frequency to avoid spam
- Set up escalation for trials ending soon with high scores
Frequently asked questions about trial conversion alerts
What events should I track for buying signals?
Key signals vary by product, but common ones include: pricing page visits, team member invitations, integration connections, export or API usage, billing page views, and usage of advanced features. Start with what you have and refine based on conversion data.
How accurate is the AI conversion scoring?
Accuracy improves as you provide feedback. Initial scores are based on common patterns. As you mark which alerts led to conversions, the AI learns your specific signals. Most teams see meaningful correlation within a few weeks of data.
What if I don't use Segment?
You can adapt this workflow for Mixpanel, Amplitude, or any event tracking system with webhook or API capabilities. The AI analysis works with event data from any source.
Should I automate the outreach too?
We recommend keeping outreach human for trial conversion. The workflow provides context and timing, but personal, relevant outreach from a real person converts better than automated emails. Use the AI suggestions as a starting point for human follow-up.