The cadence

Day -90 — Health check

For B2B accounts. CSM-driven, not automated. Reviews usage data, identifies any concerns, schedules a 30-minute “how’s it going” call if needed. The earliest signal of renewal risk shows up here.

Day -60 — Value summary

Email summarizing the year’s usage. Numbers that matter to the buyer — minutes saved, jobs scheduled, reports run. The data is real, pulled from the account, not generic. Sets the renewal conversation up to be about value delivered.

Day -30 — Renewal terms

If pricing changes are coming, this is where they’re communicated. If they’re not, this email confirms the renewal is set and asks whether they want to talk about adding seats or changing tier. Direct, scannable, no ambiguity.

Day -7 — Final notice

Confirms the auto-renewal date and amount. The legal-compliance email for jurisdictions that require it, and a courtesy for the rest. Includes the cancel path inside one click — burying it is short-term math that hurts long-term trust.