Renewals should be a moment of celebration, a chance to validate customer value and strengthen the partnership. But too often, they feel chaotic: last-minute surprises, rushed executive escalations, and deals slipping through cracks.
The truth? Predictable revenue starts with predictable renewals.
Here’s a 90-day renewal playbook your Customer Success team can adopt to move from fire drills to a repeatable process that drives retention and expansion.
Also one note before we jump in: Renewals really do start at Onboarding and I’ll talk more about that in a future episode.
Why Renewals Go Off the Rails
Most renewal chaos stems from:
Late detection of churn risk: waiting until 30 days out to address adoption gaps.
No executive alignment: economic buyers only show up when a signature is due.
CSMs flying solo: without structured support from Product, Finance, or Exec sponsors.
Unclear value proof: customers don’t see ROI in black-and-white before the invoice lands.
The antidote: start at least 90 days out with a structured, three-phase process. Depending on the size of customer you sell to you might want to start this more around 120 days out.
The 90-Day Renewal Playbook
Day 90–61: Detect & Diagnose
This is your “discovery phase.” The goal is to eliminate blind spots.
Key Actions:
Run a health check: Pull product usage, support tickets, NPS/CSAT scores, and survey results. Flag early risks.
Conduct a renewal risk review: CSM + manager identify accounts “at risk” vs. “green.” How multi-threaded are you within the account? Any changes/challenges going on in the business?
Revisit Success Plan: Ensure progress on the customer’s top 3 business outcomes is documented.
Engage champions early: Schedule a checkpoint call to review value delivered and align expectations. This also shouldn’t only be your 1 key champion. Look for good NPS feedback and engage with end-users who are champions, this feedback can be essential ammo you can utilize later on in the renewal with leadership.
Deliverables:
Renewal Risk Scorecard
Updated Success Plan
Day 60–31: Align & Elevate
Now it’s about engagement and proof.
Key Actions:
Create an Executive Value Brief: One-pager showing business outcomes, ROI metrics, and key wins.
Engage the economic buyer: Get on their calendar. Don’t wait until signature time. Make sure to gather details around their budget process and procurement process.
Map stakeholders: Identify changes in org structure, champions leaving, or new budget holders.
Socialize expansion options: If usage is strong, introduce relevant upsell/cross-sell opportunities.
Deliverables:
Executive Value Brief
Stakeholder Map
Expansion Hypotheses
Day 30–0: Negotiate & Secure
This is your closing phase. It should feel more like formalizing agreements than rescuing deals.
Key Actions:
Confirm legal/procurement timelines: Eliminate surprises around redlines or security reviews.
Engage internal sponsors: Have your VP/Exec sponsor send a note reinforcing partnership.
Enable your champion: Arm them with ROI slides and talking points for internal conversations.
Support commercial negotiation: CS, AE, and Finance work as one team, clear roles, no overlap.
Deliverables:
Renewal Proposal Packet (pricing, term, expansion options)
Executive Sponsor Note
Signed Renewal (before contract date!)
Pro Tips for Operationalizing the Playbook
Automate reminders: Use your CS platform or CRM to trigger 90/60/30-day workflows.
Build dashboards: Execs should see upcoming renewals, risk scores, and prep status at a glance.
Debrief post-renewal: Win or lose, capture lessons learned for continuous improvement.
The Payoff: Predictable Revenue
With a structured 90-day cadence, renewals shift from reactive to proactive. Customers feel valued, executives stay aligned, and your team transforms churn chaos into a predictable revenue engine.
And here’s the kicker: when done well, this playbook doesn’t just save renewals, it seeds expansion. By the time the renewal comes due, customers are already thinking about what’s next.
Action for this week: Audit your top 10 renewals coming up this quarter. Where are you today: 90, 60, or 30 days out? What actions are missing? Start putting the playbook into motion now.
