Renewal should never be a surprise conversation. The best CS teams treat the renewal conversation as the natural conclusion of a 90-day proof-of-value process that started the moment the customer signed. If you're scrambling to build a case for renewal in the week before the contract ends, the conversation is already starting from a position of weakness.
This playbook starts 60 days out and walks through exactly what to do — and what to say — at each stage.
Day 60: The renewal health check
Pull the full account history. Review: usage trends (improving, stable, or declining?), milestone completions vs. the success criteria set at kickoff, open blockers or outstanding issues, last CS touchpoint date, current health score. If usage is declining or the last CS touchpoint was more than 30 days ago, this account is at risk. Act now, not at Day 30.
Day 60 buyer re-engagement email:
Hi [Buyer name],
We're about 60 days from your renewal date, and I wanted to give you a genuine picture of where things stand before that conversation happens.
Here's what we've accomplished together this year: [3 specific wins with metrics].
Here's what I think we can do better in year two: [1–2 honest areas for improvement].
I'd like 30 minutes with you in the next two weeks to review this together and talk about what year two should look like. Would [date] or [date] work?
[Your name]
Day 45: The stakeholder alignment call
Get the buyer, at least one end user champion, and your own CS leadership on a call. The goal: confirm that the product is delivering value, address any concerns proactively, and begin discussing what year two could include. This is not a renewal pitch — it's a delivery review. The renewal emerges naturally from a positive delivery review. See our check-in templates for how to run this call.
Day 30: The renewal proposal
Send the formal renewal proposal. It should include: a summary of value delivered (your win log from onboarding and throughout the year), a comparison of the success criteria set at kickoff vs. where they are now, proposed terms for year two, and an early renewal incentive if applicable. The proposal should feel like a logical next step after the Day 45 call — not a cold ask.
Day 14: The follow-up and close
If the proposal hasn't been signed, send a follow-up that addresses the most likely objection directly. Common objections and responses:
- "We need to review the budget" → "Understood. Can we schedule a call with finance so I can answer their questions directly and make it easy for them to approve?"
- "We're evaluating other options" → "That makes sense. What specific needs are driving the evaluation? I want to make sure you have the full picture of what we can offer before making a decision."
- "We need more time" → "Of course. Would it help to extend the current contract by 30 days while you finalize the decision? That gives you flexibility without any service interruption."