Renewal Play Timing
💡TL;DR
Renewal play timing ensures you're never surprised by expiring contracts. Standard cadence: (1) 90 days—health check, value review, identify risks, (2) 60 days—expansion discussion, pricing preview, stakeholder alignment, (3) 30 days—formal renewal proposal, negotiation, signature push. Key insight: renewals are won or lost before the renewal conversation—90-day health determines 30-day outcome. Start early, intervene on risk signals, don't wait for expiration to engage.
Definition
The strategic scheduling of renewal-related outreach and activities at specific intervals before contract expiration. Typical cadence includes 90-day, 60-day, and 30-day touchpoints, each with different objectives (value reinforcement, negotiation, close).
🏢What This Means for SMB Teams
SMB SaaS often discovers renewal dates too late—scrambling at 2 weeks out. With high customer volumes and small CS teams, automated renewal scheduling is essential. Set calendar triggers at 90/60/30 days; let the system initiate outreach while CS focuses on at-risk accounts.
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📋Practical Example
A 45-person vertical SaaS ($8M ARR) had 85% gross retention but renewal conversations started at 30 days out—too late to influence churn decisions. They implemented 90/60/30 cadence: (1) 90 days: automated health score email + CSM review of at-risk, (2) 60 days: value summary + expansion opportunity call, (3) 30 days: formal proposal + signature request. Result: retention improved to 91% (saved $480K ARR), and 23% of renewals included expansion (vs. 8% before).
🔧Implementation Steps
- 1
Map renewal dates: export all contract end dates. Identify concentration risks (too many renewals in one month).
- 2
Define play cadence: what happens at 90, 60, 30 days? Who owns each touchpoint? What's the objective?
- 3
Create trigger automation: calendar reminders or CRM workflows that initiate tasks at each interval.
- 4
Build renewal collateral: value summary template, ROI recap, expansion options, pricing renewal terms.
- 5
Segment by risk: high-health accounts get lighter touch (automated email), at-risk accounts get heavy touch (CSM call, executive involvement).
❓Frequently Asked Questions
When should renewal conversations actually start?
90 days minimum for annual contracts. For multi-year or enterprise deals, start 120-180 days out. The conversation at 90 days isn't "will you renew?"—it's "how's value delivery going?" If you discover problems at 90 days, you have time to fix them. Problems discovered at 30 days become churn.
Should we auto-renew or require active renewal?
Auto-renew is better for retention metrics but can mask problems (customers forget, then churn later with resentment). Best practice: auto-renew with clear communication. Send 60-day and 30-day notices of upcoming auto-renewal with easy opt-out. This captures passive renewals while respecting customer choice.
⚡How Optifai Uses This
Optifai automatically schedules renewal plays at 90, 60, and 30 days before contract expiration. The system integrates health signals to determine touch intensity—high-health accounts receive automated outreach while at-risk accounts trigger CSM tasks and escalations. ROI Ledger tracks renewal outcomes by play timing, showing which interventions most impact retention.
📚References
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Related Terms
Customer Retention
The ability of a company to keep its customers over time, measured as retention rate (percentage of customers who continue doing business over a period).
Churn Risk Signals
Behavioral indicators that predict customer churn before it happens. Common signals include: declining login frequency, reduced feature usage, support ticket spikes, NPS score drops, billing page visits, and engagement with competitor content. Early detection enables proactive intervention.
Expansion Playbooks
Documented, repeatable sequences for upselling existing customers to higher tiers or cross-selling additional products. Includes trigger conditions, talk tracks, objection handling, and success metrics. Expansion playbooks systematize what top performers do naturally.
Sales Playbook Automation
The use of AI and workflow tools to automatically execute sales playbooks—predefined sequences of actions for specific scenarios (e.g., lost deal re-engagement, pricing page follow-up). Transforms static documentation into living, self-executing processes.