Every RevOps and sales leader knows the frustration of a pipeline full of promising deals that stall, shrink, or disappear for preventable reasons. This gap between the forecast and reality is precisely where a disciplined deal health assessment process becomes a GTM team’s most valuable asset.
To build a playbook for this, we turned to an expert with over two decades of GTM experience.
Rob Stanger, Sr Director Sales Business Partners at Twilio, is a seasoned RevOps executive who specializes in creating the support structures that empower sales teams to achieve their quotas. In a recent episode of The Go-to-Market Podcast, he broke down the essential components of deal health.
This guide distills his insights, covering everything from the unshakeable foundation of a strong ICP to the iterative frameworks and smart technology that separate winning teams from the rest.
The Unshakeable Foundation of Deal Health
Before you can assess a deal, you must know if you’re talking to the right customer. A poorly defined Ideal Customer Profile (ICP) is the number one cause of wasted sales cycles, poor customer fit, and downstream churn.
As our 2025 Benchmarks Report shows, well-qualified deals win over six times more often. A strong ICP isn’t just a filter; it’s the first and most critical stage of qualification.
Go Beyond Demographics
A truly effective ICP goes far beyond basic firmographics like company size or industry. As Stanger explained, the key is to identify the underlying operational DNA that makes a prospect a perfect fit.
He shared a powerful example from his time at a company selling a sales engagement platform. The initial ICP was simply “companies that sell software,” which was far too broad. The real breakthrough came when they pinpointed the core attribute they served: a “high velocity sales process.”
This wasn’t something you could find in a database. Instead, it was indicated by a structural signal: a high ratio of Sales Development Representatives (SDRs) to closers.
For RevOps leaders, the takeaway is clear: Dig deeper to identify the behaviors and structural attributes that signal a prospect can genuinely benefit from your solution. This transforms your ICP from a static description into a dynamic, actionable targeting tool.
What to Do When Sellers Go Rogue
It’s a common scenario: a seller, convinced they have a promising prospect, pursues a deal far outside the established ICP. Stanger’s approach is pragmatic. “Salespeople are in the trenches,” he noted. “They’re our front line… so it is important to listen.”
However, listening must be paired with coaching. While a seller might see a single commission check, the RevOps leader sees the long-term health of the business.
A deal closed with a bad-fit customer creates a chain of costly downstream issues, from implementation nightmares to inevitable churn. The role of RevOps is to support reps by aligning sales strategy with frontline execution. This means providing the data that shows why the ICP is defined the way it is, connecting it to higher lifetime value, lower churn rates, and faster implementation times.
How ICP Discipline Prevents Downstream Churn
The ultimate goal isn’t just to close a deal; it’s to create what Stanger calls a “lifelong happy customer.” The early days of HubSpot provide a classic example.
The company faced a staggering 30% churn rate by selling a narrow email marketing solution. When they realized customers were actually buying an all-in-one dashboard to manage their channels, they realigned their value proposition and saw churn plummet.
This illustrates a critical component of deal health: assessing whether the value proposition being sold can actually be delivered and valued by the customer post-sale. A disciplined ICP ensures that what you sell is what the customer truly needs, preventing the disconnect between “what we sold and what was delivered.”
Implementing a Continuous Deal Health Assessment Framework
A healthy deal doesn’t just start strong; it stays strong. Initial qualification is only the beginning. True deal health assessment is an iterative process that must be revisited throughout the sales cycle to de-risk the opportunity and ensure it continues to progress.
Expert Insight: “Deal qualification and deal health is throughout the sales process…it’s an iterative process. You go through a number of times of asking the same questions…to make sure that you understand who’s participating in the deal, why are they doing it, and what you expect the outcomes to be.” – Rob Stanger, on The Go-to-Market Podcast
1. Don’t Just Qualify Once
Using a structured qualification framework like MEDPIC (Metrics, Economic Buyer, Decision Criteria, Paper Process, Identify Pain, Champion) provides a common language for evaluating opportunities. Stanger is partial to this framework but stresses its most important aspect: it is not a one-time checklist.
Stakeholders change, budgets get reallocated, and new competitors emerge mid-cycle. A deal that looked healthy in Stage 2 can quickly become high-risk in Stage 4. Continuous process optimization means re-validating these critical elements at key stages of the deal, turning qualification into an ongoing diagnostic rather than a single event.
2. Diagnose Early
According to Stanger, when you analyze closed-lost reasons, the culprits are almost always the same simple and predictable issues. “Your biggest reasons are wrong time, no budget, and wrong stakeholder,” he stated.
This observation is a core diagnostic tool for any RevOps leader. These “Big 3” red flags are signs of poor initial qualification that often surface far too late.
- Wrong Timing: Is this an urgent, funded priority for them now?
- No Budget: Is there an allocated budget, or just interest?
- Wrong Stakeholder: Are you speaking with the economic buyer or just an influencer?
- Embed questions to screen for these at every stage.]
Selling Is a Team Sport
“Selling is not a single person sport, it’s a team sport,” Stanger emphasized, using a powerful Formula One analogy. A driver can’t win the race because of their pit crew, but they can absolutely lose it. The same is true in sales.
Sellers don’t win alone. They are supported by an entire ecosystem: Sales Engineers, Product Marketing, Customer Success, Legal, and Finance.
RevOps is your strategic partner for growth because it orchestrates this cross-functional team, ensuring every resource is deployed effectively to strengthen a deal and move it toward a successful close.
Using Technology to Enhance Deal Insight and Productivity
A solid framework and a strong team are essential, but modern RevOps teams amplify their effectiveness with technology.
From AI-powered research to intelligent forecasting, the right tools can provide deeper insights into deal health and free up reps to focus on high-value sales activities.
From Research to Outreach
Stanger shared a practical example of using generative AI to give sellers a massive advantage. His team had SDRs feed a company’s 10-K report into ChatGPT and ask it to synthesize the top three pain points mentioned. The AI-generated summary was then used to create hyper-personalized outreach. In one case, a prospect responded, “It’s like I wrote this myself.”
It turned out he had authored that section of the 10-K.
This positions AI not as a replacement for sellers, but as a productivity multiplier that gets them “90% of the way there.”
This level of top-of-funnel quality is a key driver for improving sales forecasting by ensuring the pipeline is filled with better-researched, higher-intent opportunities from the start.
Beyond Activity Scores
Stanger offered a crucial warning about the proliferation of “AI” deal scores. Many of these tools, he warned, are often just glorified activity trackers that count emails and meetings. While activity is an indicator, it doesn’t equate to progress.
A true deal health assessment platform goes beyond simple activity metrics to analyze the quality of interactions and alignment with qualification criteria.
Leaders should seek out platforms that provide genuine visibility into pipeline health and rep performance, like the pipeline visibility insights Zappi gained, to separate meaningful engagement from busywork.
The Educated Buyer
In a forward-thinking observation, Stanger noted that AI isn’t just a tool for sellers; it’s fundamentally changing how buyers educate themselves.
Before ever speaking to a rep, modern buyers use tools like Google’s AI search and ChatGPT to research solutions, compare vendors, and form opinions.
This shift requires a new approach from GTM teams. Sales and marketing content must be adapted to be “AI-consumable,” ensuring key differentiators are clear, concise, and easily surfaced by these new information brokers.
This strategic adaptation is essential for effective performance-to-plan tracking in a rapidly evolving market, a challenge that companies like Udemy have successfully navigated.
Final Thoughts
Transforming your pipeline from unpredictable to reliable depends on a robust deal health assessment playbook. As Rob Stanger’s insights reveal, this system rests on four core pillars. It begins with an unwavering commitment to a disciplined ICP defined by actionable attributes, not just surface-level demographics.
From there, it requires an iterative framework like MEDPIC, applied continuously to de-risk deals as they evolve. Success also depends on selling as a unified team, where the entire GTM “pit crew” supports every opportunity.
Finally, it involves embracing smart technology and using AI as a productivity multiplier for genuine insight.
Ultimately, high-performing RevOps isn’t about micromanaging deals; it’s about building a predictable, data-driven system that empowers sellers to win the right deals, faster. By implementing this systematic approach, leaders can build a revenue engine that is not just predictable, but resilient.
To begin building your own data-driven GTM plan, explore our guide to successful GTM planning and execution.
