Pricing problems are rarely about the price.
They’re about not knowing what you’re worth to the customers you already have. These are three versions of that problem and its solution. If any of these resonate:
[Case Study] What Are Real Estate Brokers Actually Buying?
A PE-backed real estate software company had 10 acquired products, each with its own pricing logic and little overlap. After five years without a comprehensive pricing review, they knew something was wrong. Discounts were becoming standard. Average contract values were stalling as the real estate market got tougher. Brokerages were getting smaller and facing their own margin pressures.
There was no way to look at pricing comprehensively across the 10 products and 3 distinct customer segments.
The Discovery
Through customer research and sales data analysis, we found brokers weren’t buying software features or product suites. They were buying transaction efficiency and agent retention.
Average transaction volume varied widely by brokerage size and agent ambitions. The existing pricing model had large firms low-volume firms paying substantially more than smaller high-volume firms. Plus, there was no pricing guidance for brokerages above a certain size, resulting in leaving $393,000 on the table for just one product.
The Breakthrough
Once we understood what brokers were actually buying, the architecture became straightforward. Instead of 10 disconnected pricing models, we built one unified structure around transaction volume. Aligning the brokerages’ business incentives to the software pricing.
One architecture. All 10 products. Three distinct customer segments spanning 2 to 15,000 agents.
The Result
The gap closed. Not from new customers, not from raising prices arbitrarily, but from pricing that finally matched the customers business.
Sales teams had a clear story connecting price to broker growth. Cross-sell and upsell became logical progressions. Deal-by-deal negotiation stopped. Discounting stopped being the default.
The Lesson
Optimizing price points without knowing what customers are buying produces marginal improvements at best. Knowing what they’re actually paying for first produces step-function growth opportunities.
[Case Study] When a Segmentation Problem Appears as a Pricing Problem.
A premium B2B SaaS company wanted to expand into smaller customers in their target segment, but their pricing was blocking them. Small prospects would choose “nothing” over committing to the premium price point.
The incoming CEO asked us to “make pricing more approachable at the low end.”
But that wasn’t the real problem.
The Discovery
Through value-to-price analysis and customer research, we found that small and large customers were buying fundamentally different outcomes:
Small customers were buying:
- Core functionality
- Well-known integrations
- Straight-forward analysis
Large customers were buying:
- Collaboration and coordination
- Complex integration with enterprise systems
- Comprehensive support and partnership
They were selling ONE product to two different customer types who valued completely different things. Priced it as if everyone had the same complex needs.
The Solution
We didn’t lower pricing. We unbundled based on what each segment was actually buying:
- Small customers: Streamlined core outcomes they valued, removing features they didn’t need, want, or use.
- Large customers: Premium pricing maintained for comprehensive enterprise capabilities
- Clear upgrade path: As small customers grew, expansion was driven by their own growth and adoption of more sophisticated systems,
The new pricing model stayed within the recommended value-to-price range from smallest to largest customer—but now reflected actual value delivered to each segment.
The Result
- More approachable for small customers without cheapening the premium brand
- Maintained high-end positioning for enterprise buyers
- Created upsell revenue opportunities by unbundling previously included features
- Expanded addressable market across a larger customer base while preserving margins
The Lesson
“Make it cheaper” is rarely the answer. Understanding different customers needs and designing appropriate packaging creates growth without cannabalization.
[Case Study] They Were About to Underprice a $2M Deal Again
A B2B AgTech SaaS company was winning deals but losing money. Thin margins and operational challenges were dragging down growth. Now they faced a high-stakes enterprise opportunity—and the CRO knew their standard playbook would lead to dramatic underpricing and potentially long-term operational problems.
They reached out asking us to help price this specific deal. We asked: “What is this customer actually buying?”
The Discovery
Through discovery sessions with all key stakeholders at the prospect’s company, we found the customer wasn’t buying software. They were buying five distinct business outcomes:
- Millions in incremental revenue from operational improvements.
- Hundreds of thousands in operational cost savings.
- Risk mitigation avoiding costly compliance exposure.
- Competitive advantage through better data and faster decisions.
- Organizational efficiency reducing manual processes across teams.
Every one of those outcomes was quantifiable. The CRO had been pricing implementation costs and usage. The customer was buying business outcomes worth ten times what the proposal would have said.
All value can be quantified. This company hadn’t done that work yet.
The Breakthrough
We built a pricing framework around the five distinct customer benefits. Each quantified to a recommended price range. The conversation shifted from software cost to value delivered.
Providing the CRO with the confidence to hold a number reflecting the customers’ comprehensive value.
The Result
- The deal closed at a dramatically higher price point than any previous engagement.
- The framework became the primary tool for pricing all subsequent enterprise opportunities.
- They were worth more than they were charging. They just hadn’t quantified it yet.
The Lesson
If you don’t know what the customer is actually buying, you’ll price what you’re selling. Enterprise customers aren’t buying software. They’re buying outcomes. And outcomes, every one of them, can be quantified.
If any of these felt familiar, the next step is a 75-minute Value Blindspot Session. $1,500. If we work together, it applies toward the engagement.