Robin Landy , a leading expert in software pricing strategy, delivered an insightful talk at BoS Europe 2025 focused on moving beyond simple price points to create sophisticated pricing structures based on customer value and segmentation.
He highlighted that many successful software companies still rely on outdated pricing structures (sometimes the same ones set by founders on day one), which are often suboptimal and fail to capture the increasing value delivered by continuous product development.
Robin introduced the concept of “The Monolith,” a metaphor coined by Danish pricing expert Ulrik Lehrskov-Schmidt, which describes bad pricing structures that absorb all new features without raising prices or diversifying the model.
The consequence of maintaining a Monolith is delivering ever more value for ever less money.
He shared a compelling case study about a client whose product feature was so fundamentally misaligned with customer interests that they likely would have paid to disable it (a “Job Not to be Done”), emphasizing the danger of prioritizing features customers actively dislike,. This particular problematic feature was a pretty bulletproof audit trail that could expose non-quality/non-price related contract awards in turbine maintenance.
The core message is clear: businesses must prioritize pricing for their customers, not just pricing their product.
Key Takeaways for Pricing Strategy and Feature Validation
1. Price for Segmentation, Not Just Price Point
Price point should be the last decision made in the pricing process,. Pricing strategy must be built from the top down, following this structure:
- Proposition: What value are you delivering?
- Customer Segments: Identify groups with differing requirements and willingness to pay.
- Packaging: Define what features or access levels are included for these segments (e.g., unlimited access vs. restricted resolution/screens),.
- Pricing Model: Choose how customers pay (e.g., recurring subscription, setup fees, prepaid credits, units of work).
- Price Point: Finally, set the monetary cost.
2. Recognize the Pitfalls of Simple Pricing
While simple pricing is instinctively attractive, it can be detrimental. Overly simple pricing prevents segmentation by value, meaning high-value customers pay the same as low-value ones. Furthermore, it gives sophisticated enterprise customers and procurement managers a single target number to negotiate against, making it harder to protect margins.
Introducing a more complex structure provides levers (like platform fees, support add-ons, or segmented tiers) for negotiation.
3. Use Points Allocation to Benchmark Feature Value
Points allocation is a “boring sounding tool” that is criminally underused but incredibly effective for identifying which features customers value most highly, and especially relative to existing features they already pay for.
• Execution: Ask customers (current, potential, or ex-) to allocate a fixed number of points (e.g., 200) across a list of features (current, roadmapped, potential) based on perceived usefulness within their organization,,.
• Running Commentary: Crucially, require customers to give a running commentary as they allocate points. This qualitative feedback helps uncover the true context behind why a feature is valued (e.g., saving time, driving revenue, hitting specific KPIs),.
• Segmentation Insight: This exercise often reveals emerging customer segments that place exceptionally high value on a particular new feature, indicating an opportunity for a premium tier.
4. Employ the Van Westendorp Price Sensitivity Meter (VWPSM)
To translate perceived value into concrete pricing indicators, the VWPSM is a useful, albeit cumbersome-sounding, tool. Directly asking customers “how much would you pay?” is rarely useful as answers may be biased (trying to be nice or anticipating negotiation).
The VWPSM instead uses four key questions to establish a zone of acceptable pricing:
- At what price is the product expensive (but still considerable)?
- At what price is the product so expensive you wouldn’t buy it?
- At what price is the product so cheap that you’d question the quality?
- At what price would you consider the product a bargain?
5. Avoid Developing “Jobs Not to Be Done”
A “Job Not to Be Done” is a feature that is so severely misaligned with customer interest that they would pay to have it removed.
The risk is creating something that actively undermines the core proposition, as illustrated by the client whose bulletproof audit trail feature was a “deal killer” because it threatened transparency in a corruption-prone market.
Rigorous feature prioritization and continuous customer development interviews (like points allocation) are essential to prevent resources from being wasted on features customers may actively despise.
Landy’s talk implies that if you are not running value validation exercises, you risk building features your customers would happily pay you to remove.
Don’t miss it. Watch now: https://businessofsoftware.org/talks/finding-features-customers-will-pay-more-for/?utm_medium=social&utm_campaign=BoSEU26promo&utm_source=LinkedIn