Build trial-risk scoring from first-session engagement signals
Use time-to-first-action and template interaction data to flag at-risk trials for sales outreach within 24 hours — catching activation friction before users churn, and giving sales actionable risk data in admin.
Definition of done
Show a contextual prompt with workflow templates after workspace creation, track template_selected events, and reduce the workspace-to-first-action drop-off rate.
I scanned the repo — Rails API with a React SPA, Stripe billing via a webhooks/ controller, and a multi-step invite flow in app/services/onboarding/. The Segment integration has event gaps across the trial activation path.
Before I set goals: is the immediate priority improving trial-to-paid conversion, or expansion revenue from existing accounts?
01:02 PM
Trial conversion — we are losing people between invite accept and first workflow run. Sales also needs usage snapshots in admin, they keep pinging engineering for one-off queries.
01:05 PM
Got it. Two goals:
Reduce trial-to-paid activation friction inside first session
strategicinstrument the full invite-to-first-action funnel, isolate the biggest drop-off, and ship targeted fixes.
Give sales a reliable workspace-usage snapshot in admin
strategicsurface health scores, seat utilization, and MRR on account cards so sales stops needing ad-hoc queries.
Starting with the onboarding funnel instrumentation for goal 1 — that is the diagnostic work the activation friction fixes depend on. I'll work on the admin snapshot in parallel since it's independent.
01:08 PM
Finished instrumenting the onboarding funnel — first milestone for the activation friction goal is done. Here is what the data shows after 48 hours of collection:
- Invite accept → workspace created: 89% completion, healthy
- Workspace created → first workflow run: only 38% completion — this is the cliff
- Of the 62% who drop off, 81% never return after their first session
- Median time-to-first-action for users who convert: 4m 12s vs 11m+ for those who don't
The gap is not invite friction — it is the dead air between creating a workspace and knowing what to do next. Users who hit a workflow template within 3 minutes convert at 2.4× the rate of those who don't.
Meanwhile, the admin snapshot goal is progressing — workspace health scores and seat utilization are already live on account cards. Sales has the usage data they were requesting.
03:30 PM
Based on those numbers, two milestones to keep pushing on the activation friction goal:
Add a guided first-action prompt after workspace creation
Surface the three most relevant workflow templates right after setup, targeting the 62% drop-off window before users bounce. This is the highest-leverage fix for reducing trial-to-paid friction.
Build trial-risk scoring from first-session engagement signals
Use time-to-first-action and template interaction data to flag at-risk trials for sales outreach within 24 hours. This also feeds the admin snapshot goal — trial risk scores will surface alongside the health scores sales already has.
The second depends on the first — we need the template interaction events wired up before the scoring model has useful signal.
03:31 PM