Automate trial user outreach by responding to what a trial user did, not to the day they signed up.

Choose a signal that deserves a message.

A user who invited a teammate, completed a setup step, or returned to the product has a different question from someone who never reached the first meaningful action. Start by defining the signals that your team believes are useful, not merely available.

Ask Strawberry to group accounts by those signals and state the evidence for each suggested touch. This prevents a full trial cohort from becoming an undifferentiated email list.

Bring the relevant context into the draft.

A useful message might point to the feature a user just tried, answer a support question, offer a setup tip, or ask whether the team is blocked. It should not pretend the sender watched every click or know facts outside the product relationship.

Prepare a short draft with the account’s relevant activity, prior conversation, and a clear reason for reaching out. Review it for accuracy and tone before it goes anywhere.

Route friction to help rather than another sequence.

Some trial users need a tutorial.

Others have a billing question, a bug, a security review, or a request that belongs with sales. A good workflow labels the likely next owner instead of escalating every issue through marketing copy.

Save the routing rules as a customer-success skill once the team agrees them. A routine can surface the queue, while account owners decide which message, meeting, or support handoff is appropriate.

Measure whether the message helped the next action.

Open rate is not the full outcome.

Track whether the user completed the relevant activation step, received a useful answer, booked help, or told you the outreach was not relevant.

Use those results to remove weak triggers and improve the next queue. The goal is fewer better-timed conversations, not a longer automated cadence.

Frequently asked questions