The problem in numbers
Answer two questions from your CRM, without opening a spreadsheet. Which contracts renew in the next ninety days, and what is their combined value. If Pipedrive cannot answer, your renewals are unmanaged, whatever the spreadsheet says. The spreadsheet does not chase anyone, does not escalate, and does not appear in the Monday review.
The cost hides in asymmetry. Winning a new customer takes months of pipeline work. Losing one takes a single missed renewal conversation, and research on retention economics agrees on the direction: keeping a customer costs a fraction of replacing one. Yet most CRMs we audit give new business ten stages of structure and renewals none. The revenue you defend deserves the machinery you give the revenue you chase.
The design
Create a dedicated Renewals pipeline. The process differs from new business, and differing process is the one legitimate reason to add a pipeline, as pipeline design lays out. Four stages carry most renewal motions: Upcoming, for deals surfaced inside the ninety-day window. Health check held, after the conversation that surfaces risk and expansion signals. In negotiation, for terms, pricing and paperwork. Committed, when the customer confirmed and only signature remains. Won is the renewal signed. Lost is churn, with a reason, and those reasons become your churn analysis for free.
Two custom fields make it run: Contract end date on the deal or organisation, and MRR or annual contract value if you track recurring value separately from deal value. The creation rule: when a new business deal is won, a renewal deal is born immediately, value set to the recurring amount, owner set to whoever holds year two, expected close set to the contract end date. A workflow automation on deal won creates and copies most of this. Pipedrive's automations do not do date arithmetic well, so either the rep sets the contract end date as part of the won checklist, or a small middleware step calculates it. Never let the date default to blank.
The early warning is a filter, not a feeling: renewal deals whose contract end date falls inside ninety days and which still sit in Upcoming. That filter is the renewal owner's working list and the manager's escalation view. Add rotting on the active stages, with generous thresholds, so a renewal that stalls mid-negotiation turns visibly red weeks before the deadline.
Implementation steps
Step one: backfill. Create renewal deals for every live contract, from the contract list, before wiring any automation. The pipeline must be complete on day one or nobody trusts its totals. Step two: add the fields and build the creation automation for future wins. Step three: build the ninety-day filter and put it in the weekly review agenda. Step four: define the health check as a real activity type with an owner, so stage two means something happened. Step five: agree the escalation rule, for example any renewal not in Committed thirty days before end date goes to management. SaaS teams will recognise this as the renewal half of the setup described in Pipedrive for SaaS.
How you measure that it works
Gross renewal rate by count and by value, quarterly, straight from won versus lost in this pipeline. Average days between renewal won and contract end: rising is good, because early closes mean the ninety-day machine works. Share of renewals still in Upcoming inside thirty days of end date: should trend to zero. And churn reasons from the lost deals, reviewed quarterly, because three churns citing the same product gap are a roadmap signal wearing a sales costume. Renewal value also stops contaminating your new business forecast, which improves both numbers at once.
Common failure modes
The optimistic default: renewal deals created at one hundred percent assumed, worked by nobody, then lost in bulk. The health check stage exists to force real contact into every cycle. The date desert: contract end dates missing or wrong, so the ninety-day filter lies. Make the date a required field at renewal deal creation and audit it in your hygiene routine. The upsell blur: expansion stuffed into renewal deals until nobody knows what renewal rate means. Separate deals, separate pipelines, honest numbers. And the ownership vacuum between sales and customer success, where each assumes the other is handling year two. The deal owner field decides it per contract, visibly, which is the entire point of running renewals as deals.