This blog is authored by Jenn Harvey of Jennifer Harvey Consulting, and Jeff Saenger, VP of Customer Success at Terret.
A typical Monday morning executive meeting: The CRO asks why Q1 retention is projected at 82% when last week it was 85%. The renewal leader hesitates, mentions "changing customer signals," but struggles to explain which specific deals shifted and why. Sound familiar?
For most SaaS companies, renewal forecasting remains frustratingly imprecise. Many organizations struggle with significant gaps between what they forecast and what actually closes—a variance that translates into misallocated resources and missed opportunities. When renewal forecasts are off, companies may over- or under-staff, make poor investment decisions, or face uncomfortable conversations with investors and board members.
The problem isn't your team's experience—it's that traditional forecasting relies on subjective assessments without a structured framework. When a rep places a deal in "Commit" versus "Best Case," what objective criteria are they using? And do those criteria mean the same thing across your entire team?
Milestone-Based Forecasting transforms renewal forecasting from intuitive art to data-driven science by anchoring forecast categories to specific, observable customer actions. This approach dramatically improves accuracy while creating organizational alignment.
This article explores how to define critical milestones, map them to forecast categories, and embed them into your operational rhythms.
"This deal is definitely going to close."
Every renewal leader has heard this confident prediction – and has felt the pain when that deal slips at the last minute. The traditional forecasting categories (Pipeline, Upside. Best Case, Commit) provide basic structure – but without clear and objective criteria for categorization, inconsistencies and bias inevitably seep in:
Without standardized criteria, deals with similar characteristics might be classified differently depending on who's doing the forecasting. This doesn't just create forecasting headaches—it undermines leadership trust and complicates resource allocation.
Often, slipped deals share a common pattern: customers expressed satisfaction but never explicitly confirmed renewal plans or budget.
The organizational cost extends beyond missed forecasts. When forecasting lacks rigor, leadership questions all numbers, creating a culture of second-guessing and constant explanations that distracts from actual customer work.
In our experience working with numerous renewal processes, four milestones consistently emerge as the most predictive, concrete indicators:
This milestone is achieved when the customer explicitly states they will recommend renewal. Not just general satisfaction, but a clear affirmation in response to a direct question.
How to secure it:
This milestone confirms that budget has been allocated for the renewal.
How to secure it:
This milestone establishes a clear, agreed-upon schedule for completing the renewal process.
How to secure it:
This milestone confirms all parties understand exactly what needs to happen to finalize the renewal, with clear ownership and timing.
How to secure it:
Each milestone represents an objective, observable event—not a feeling or interpretation. This objectivity is what transforms forecasting from guesswork to science. When every team member uses these same milestones to assess deals, forecast consistency improves dramatically.
Once you've defined your critical milestones, the next step is mapping them to your forecast categories. This creates a clear, objective framework that anyone in your organization can apply consistently.
Below is a sample mapping framework that connects milestone achievement to specific forecast categories:
| Forecast Category |
Customer Recommendation |
Budget Approved |
Mutual Timeline |
Closing Plan |
| Won |
✓ |
✓ |
✓ |
✓ (Executed) |
| Commit |
✓ |
✓ |
✓ |
✓ |
| Best Case |
✓ |
✗ |
✗ |
✓ |
| Upside |
✗ |
✗ |
✗ |
✓ |
| Pipeline |
✗ |
✗ |
✗ |
✗ |
Create clear guidelines for ambiguous situations:
Remember, the goal isn't perfect prediction but consistent, objective assessment. This framework won't guarantee that every "Commit" deal closes, but it ensures that all deals labeled "Commit" share the same objective characteristics, dramatically improving your ability to forecast accurately.
Even the best framework won’t reach its full potential without consistent application. To successfully implement milestone-based forecasting in your organization, focus on two key areas: technology enablement and operational cadence.
CRM Setup
Configure your CRM to track milestones explicitly:
Pipeline Meetings
Transform review meetings to focus on milestone achievement:
A milestone-focused pipeline review might include questions like:
This milestone-centric approach creates natural alignment between forecast categories and concrete next steps. Rather than general direction to "move the deal forward," teams focus on securing specific milestones with clear actions.
Milestone-Based Forecasting transforms renewal forecasting from subjective guesswork to a structured, data-driven process. By tying forecast categories to specific customer actions, companies can improve forecast accuracy, strengthen sales accountability, and provide leadership with reliable revenue insights.
The Benefits are clear:
✔ Higher forecast accuracy
✔ More predictable revenue outcomes
✔ Improved sales team accountability
✔ Increased confidence from finance and leadership
Transitioning to milestone-based forecasting requires alignment and operational rigor—but the payoff in forecast accuracy and business stability makes it worth the effort. Now is the time to implement this framework and take your renewal forecasting to the next level.