This workflow turns SaaS trials into paid customers by guiding new users toward activation over WhatsApp, branching by product usage, and sending the upgrade prompt only when the account has seen enough value to convert.
At a glance
| |
|---|
| Trigger | Trial started |
| Channels | WhatsApp |
| Templates | 3 (welcome, activation nudges, upgrade Flow) |
| Typical cycle | 7 to 14 days |
| Platforms | HubSpot, Stripe |
What this workflow does
On day 0 the user gets a warm welcome and an offer of help. Over the trial, usage-based branching decides the messaging: activated users are nudged toward the upgrade, while stalled users get setup help and a rescue path. The upgrade Flow lets the user pick a plan and convert in chat through Stripe, with billing starting after the trial.
What you will need
- A trial-started signal from your product, synced to a HubSpot property
- WhatsApp templates for welcome, activation help, and an upgrade Flow
- Stripe connected for in-chat plan selection
- An activation property (for example, a key action completed)
Workflow steps
- Trigger trial started property set in HubSpot.
- Day 0 welcome confirm the trial length and offer help.
- Activation branch if the activation event has fired, proceed toward upgrade. If not, send setup help and offer a Customer Agent.
- Upgrade Flow (around day 10) send the plan picker, reassuring the user that their data and workflows are kept and billing starts after the trial.
- Convert on plan selection through Stripe, send a confirmation and set the account to paid. Exit the nudge track.
- Trial ending, no upgrade send a final value reminder before expiry, then move to a win-back cadence.
WhatsApp templates
tmpl_trial_welcome trial welcome with help options (Marketing category)- Activation nudge template
tmpl_trial_help upgrade Flow with plan picker (Utility category)
Tips and gotchas
Gate the upgrade prompt on a real activation signal, not just elapsed days. Asking an inactive trial to pay converts poorly and burns goodwill.
