When most teams think about pricing, they jump to the headline question: Should we charge more?
Sometimes the answer is yes. But in many businesses — whether you're selling software, services, hardware, or anything in between — the bigger opportunity sits one layer deeper: How should we package value?
This is one of the most common — and highest-impact — use cases for the Digital Pricing Officer (DPO). Packaging strategy sits at the intersection of product, pricing, sales, and customer success. Done well, it helps customers self-select into the right offer, makes value easier to understand, creates a natural upgrade path, and improves expansion economics over time. Done poorly, it creates confusion, suppresses willingness to pay, and leaves growth on the table — even when the underlying product or service is strong.
What the Digital Pricing Officer Actually Looks For
The DPO doesn't just ask whether your prices are too high or too low. It evaluates whether the structure of your offer matches how customers buy, use, and grow.
That typically means diagnosing five things.
1. Segment-to-package fit
Are your packages built around how different customers derive value — or around your internal product architecture?
Many companies still bundle offerings based on how they built the product rather than how customers buy it. Strong packaging reflects real customer segments: company size, complexity, use case, usage intensity, number of locations, or operational maturity.
When very different customer types are forced into the same bundle structure, one of two things usually happens: lower-value buyers feel overcharged, or higher-value buyers are under-monetized. Often both.
2. Feature placement
Are your highest-value features in the right tiers?
A useful packaging lens is to classify capabilities into three buckets:
- Leaders — features that drive the purchase decision
- Fillers — features that support the experience
- Killers — features that add complexity without adding perceived value
This matters because many companies either overstuff lower tiers (weakening upgrade logic) or hide too much value in upper tiers (reducing adoption of retention-driving features). The DPO helps identify which features should anchor a tier, support a tier, be gated for upsell, or be offered as standalone modules.
3. Adoption vs. availability
If a feature exists but isn't being used, is that actually a product problem?
Often, it isn't. Low adoption can reflect poor onboarding, implementation friction, unclear value communication, bad feature placement, or missing commercial incentives — not product weakness.
In one restaurant technology engagement, a company's mid-tier plan was competitively priced and widely adopted, but two high-retention capabilities — kitchen display and payroll/tips — showed materially lower adoption than industry benchmarks. The product existed. The issue was that the packaging and onboarding model weren't making activation easy enough at that tier.
That kind of insight changes the conversation entirely. Instead of asking "Should we build more?" the business can ask: Should onboarding be bundled? Should implementation support be included at this tier? Should these capabilities be more prominently positioned in the offer?
4. Monetization model design
Are you relying too heavily on flat subscription fees?
Best-in-class SaaS pricing increasingly combines subscription tiers, usage-based elements, modular add-ons, volume commitments, and segment-specific terms — because different monetization levers serve different goals. Flat fees simplify buying. Usage-based pricing aligns cost with realized value. Add-ons monetize advanced needs without cluttering core tiers.
A DPO evaluates whether you're missing monetization levers that competitors or adjacent SaaS models already use effectively.
5. Economic impact
Will a packaging change improve revenue quality, not just price realization?
Good packaging strategy should support expansion, retention, sales efficiency, lower discounting, faster time to value, and stronger NRR. The best packaging work isn't just a pricing project — it's an operating model improvement.
A Pattern That Shows Up Repeatedly
Here's a scenario that's surprisingly common across industries:
The mid-tier plan becomes the default landing zone. Adoption concentrates there. The breadth of features or services expands over time. Pricing stays largely unchanged. Some premium offerings get under-activated. Sales starts making exceptions at the top end. And leadership senses that monetization is lagging behind the value being delivered — but can't quite pinpoint why.
This is exactly where a Digital Pricing Officer adds value.
A DPO can quickly evaluate whether the mid-tier is underpriced relative to market, whether customers are over-consuming value at current price points, whether the upgrade path is compelling enough, and what the likely ARR and NRR impact of a repackaging effort could be.
In the restaurant-tech example above, two signals stood out: a growth-tier package priced below market median despite strong customer usage, and high-retention features not activating at expected rates. The first points to under-monetization. The second points to packaging and enablement design — not price level. Both are solvable, but they require different interventions.
What the Output Typically Looks Like
A strong packaging evaluation usually results in a concrete set of recommendations:
Re-tier the offer. Clarify what belongs in Starter, Growth, Pro, and Enterprise so each plan reflects a distinct customer need and economic profile — not just a feature list.
Re-anchor the middle. If the mid-tier is where most customers land, it needs to do a lot of work: communicate differentiated value, support healthy margins, and create genuine room for upsell — without becoming an underpriced catch-all.
Promote retention-driving features earlier. If certain capabilities reduce churn or increase stickiness, they may deserve stronger placement, bundled onboarding, or activation support — not burial in a higher tier.
Add a monetization lever. Introduce usage-based components, add-ons, or segment-differentiated pricing where the product and market can support it.
Improve enterprise discipline. Replace ad hoc discounting with an explicit volume-tier structure or packaged enterprise terms.
Why This Matters Now
As companies add offerings, serve broader customer bases, and pursue efficient growth, the old "three plans and a price page" model often stops working. The challenge is no longer just creating value — it's organizing and communicating it.
A lot of companies think they have a pricing problem when they actually have a packaging problem. If your plans no longer reflect how customers buy, how they derive value, or how they grow, then even a well-calibrated headline price won't fix the underlying issue.
The job of a Digital Pricing Officer is to make that visible — and turn it into an actionable roadmap.
Because pricing isn't just about charging more. It's about designing better choices.
Sources: Flame & Fork Industry and Benchmark Report; Flame & Fork Company Summary; OpenView SaaS Pricing eBook 2019; EY SaaS Packaging Design; Bessemer The Startup Pricing Journey; PPS Pricing Advisor September 2024
