Beyond “Pricing”
A Strategic Guide for Sales Leaders to Decode Why You’re Losing Deals
You’ve heard it a hundred times: “We lost on price.”
It’s a neat, tidy explanation—easy to say, hard to dispute. But if you’re in the business of driving revenue, you know that answer doesn’t hold water for long.
As sales leaders, we’re under constant pressure to deliver results—quarter after quarter. Yet too often, the real reasons deals slip away are left in the dark. Relying on “price” as a scapegoat can be fatal to growth because it blinds us to the systemic issues we need to fix.
At Thirdside, we’ve spent years conducting thousands of win-loss interviews across industries. What we’ve seen time and time again: price is rarely the real reason for lost deals—it’s just the convenient excuse.
Let’s unpack why this myth persists, what’s actually going on behind the scenes, and how senior sales leaders can harness these insights to sharpen their entire go-to-market motion.
The “Price” Excuse: A Convenient Myth That Hides Deeper Issues
When deals don’t close, the easiest explanation is to blame the price. It’s the one factor that’s obvious and doesn’t require uncomfortable conversations about sales performance, product fit, or go-to-market alignment.
But here’s the truth:
Most of the time, “price” is a proxy for something else.
What it usually hides:
- Confusion: Buyers couldn’t understand how your pricing model actually worked.
- Value Misalignment: They didn’t see enough value to justify the spend.
- Implementation Anxiety: They worried your solution wouldn’t work in their environment.
- Competitive Fit: Another vendor felt like a better match—even at a higher price.
When price is the stated reason, it often means buyers don’t see the ROI—or can’t connect the dots. That’s not a pricing issue—it’s a value communication issue.
Why CRM Data Misses the Mark (and How That Hurts Your Strategy)
Here’s the uncomfortable reality: CRM loss reasons are wrong 75% of the time.
We see this in our work every day. Reps need to move on to the next opportunity—understandable. But that also means the data they log is typically:
- Vague (“Pricing,” “Competition,” “Timing”)
- Incomplete (no nuance or customer-side detail)
- Politically safe (no one wants to log “We didn’t understand their needs”)
For senior leaders, this poses a dangerous trap. If you’re making pipeline decisions, forecasting, or coaching based on that data—you’re building your growth strategy on shaky ground.
Why Leadership-Level Insights Require Third-Party Conversations
Here’s the challenge:
Your reps can’t—and shouldn’t—do this level of discovery themselves. Even the best reps have biases. They’re too close to the deal. And let’s be honest—no buyer wants to say, “Your team dropped the ball” to the person who was on the call.
This is why win-loss interviews by an independent third party are so critical.
What sets these conversations apart?
- Buyers open up. There’s no risk of hurting feelings or getting pitched again.
- Deeper truths emerge. Buyers reveal fears, concerns, and perceptions they never shared during the sales cycle.
- Quotes that resonate. Leadership hears the real voice of the buyer—not a sanitized bullet point in a CRM.
For sales leaders, these aren’t just “nice-to-know” insights. They’re the foundation for better strategic decisions—across every part of your go-to-market motion.
What Senior Sales Leaders Can Do With These Insights
Armed with these candid conversations, senior sales leaders have the clarity to take action where it matters most—beyond just coaching individual reps.
Here’s how these insights can shift your strategy:
Validate (or Refine) Your ICP
- Are you consistently losing to the same types of competitors?
- Are you pursuing segments where your value prop doesn’t resonate?
- Win-loss insights show if your ideal customer profile is truly ideal—or just convenient.
Fix Misaligned Messaging
- If buyers don’t see how your solution addresses their unique challenges, you’re stuck in price wars.
- Win-loss interviews reveal what really matters to buyers—and what’s just noise.
Bridge the Gap Between Product and Sales
- Leadership can use these insights to bring product teams into the revenue conversation.
- If deals stall because of feature gaps or integration fears, product needs to hear that directly.
Sharpen Forecasting and Pipeline Reviews
- Instead of relying on shaky CRM data, you can bring real buyer perceptions into deal reviews.
- This improves forecast accuracy and confidence.
Build a Culture of Curiosity
—Not Blame
- When your team sees that lost deals are rarely one rep’s fault, but often about systemic misalignment, you create a culture of continuous improvement.
Real-World Examples of “Price” Masking Deeper Problems
Here’s what we’ve heard in interviews—direct from buyers:
“The price was high—but honestly, we couldn’t see how it would work with our existing systems.”
— Mid-market CIO
“The demos were too generic. We never felt they understood our use case.”
— Head of Operations, SaaS company
“The features sounded great, but our team was confused about how it would fit with our workflows. Another vendor nailed that.”
— IT Director, Healthcare
In each case, price wasn’t the real blocker.
It was value clarity, alignment, and trust.
From our own research:
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- Pricing Complexity as the Real Barrier
A mobile app development platform came to us, convinced they were losing deals because of high prices. Our interviews revealed the real issue wasn’t the amount—it was the confusion. Prospects didn’t understand how to calculate costs beyond year one. This complexity scared them away, handing wins to competitors who could paint a clearer picture of long-term value. - Wrong Messaging, Wrong Buyers
Another client—a big data analytics company—thought their pitch was rock-solid. But win-loss interviews revealed they were targeting data visualization teams instead of data stewardship teams who cared more about accuracy than flashy dashboards. They weren’t losing on price—they were fighting the wrong battle altogether. - Relationship Risk Overlooked
For one SaaS vendor, they believed churn was about feature gaps. But interviews showed that when a key champion left the customer organization, their solution lost momentum—no matter how robust the product was. This was a “relationship risk,” not a “price risk,” and it needed a different kind of sales enablement focus.
- Pricing Complexity as the Real Barrier
answers
FAQ’s
Leadership-Level Insights
Why is “price” so often blamed, even if it’s not the real reason?
Price is the most convenient scapegoat. It doesn’t challenge your sales process, your product roadmap, or your positioning. But real growth only happens when you’re brave enough to look beyond the easy answers.
How can we separate “price” from “value mismatch”?
Independent win-loss interviews ask questions your reps can’t—and reveal whether buyers saw a clear ROI story. If they didn’t, that’s a strategic gap, not a budget issue.
We already have post-sale surveys—why isn’t that enough?
Surveys skim the surface. Real conversations pull out the nuance. Buyers don’t hold back in a live conversation with a neutral interviewer—and that’s where the gold is.
How quickly can we expect to see real improvements from this?
Most leaders start seeing actionable trends within a quarter. Once these insights inform your coaching, product conversations, and messaging alignment, win rates typically rise within 6-12 months.
How does this align with expansion and customer success efforts?
The same reasons you lose new deals often show up in expansions and churn. Fixing these blind spots doesn’t just help you close new logos—it helps you keep and grow existing ones.
Is there an ideal cadence for these interviews?
We recommend a quarterly cadence. This keeps your insights current and ensures you’re adapting as buyer needs evolve.
Should we try to do this internally?
While it’s possible, it’s hard for internal teams to overcome biases—and buyers are far more candid with a third party. For leadership teams, independent insights are more credible and easier to act on.
How should we introduce this process internally?
Set the tone that this isn’t about blame—it’s about truth. Share with your team that it’s an opportunity to fix what’s really costing revenue, not to point fingers.