Pricing & Packaging: How to Get It Right
Enterprise SaaS companies often underestimate how much influence pricing and packaging have on their ability to grow. Leaders typically acknowledge their importance but often treat them as financial details or late-stage decisions tied to a release. In reality, pricing and packaging shape almost every aspect of go-to-market success. They influence how buyers understand value, how sales teams position the product, how customers expand, and how predictable revenue ultimately becomes.
I’ve learned this the hard way over the years. Pricing has a way of exposing gaps that are already sitting inside the business: unclear segmentation, inconsistent positioning, packaging that no longer reflects product strategy, or simply a lack of alignment on what creates value. When pricing feels complicated, it’s almost never because the “number” is wrong — it’s because something upstream needs clarity. Strong pricing is built on insight, alignment, and shared understanding. It is not a spreadsheet exercise. It is an operating system for scale.
I wrote this guide because I’m currently working through a complex pricing and packaging initiative, and I found myself documenting the patterns, lessons, and signals I rely on over and over again. What follows is the same framework I use with SaaS teams navigating pricing resets: where to begin, what information to gather, how to evaluate willingness to pay, how to price new and existing products, how to simplify SKUs, how to sunset offerings responsibly, and how to build governance that keeps pricing from falling behind again.
Why Pricing and Packaging Matter More Than Most Realize
Pricing in enterprise software is one of the most strategic decisions a company makes. Unfortunately, it is often shaped by the wrong inputs, such as competitor price points, gut feelings, or fear that a higher price will slow deals. Pricing is fundamentally about alignment. It needs to align with the value created, the outcomes delivered, and the customers that the business intends to serve.
McKinsey’s research shows shows that pricing improvements have a larger impact on profitability than almost any other lever. In many cases, pricing has 2–4x the impact of improving acquisition or reducing churn. In my experience, the most visible benefit inside an organization isn’t just margin lift; it’s how much smoother conversations become between Sales, Product, and Finance once the model actually makes sense to everyone.
Pricing is also receiving closer scrutiny inside enterprise organizations. Finance and procurement teams now play a far more active role in software evaluation as organizations place greater emphasis on measurable value, predictability, and cost discipline. I rarely see large opportunities close now without someone asking, “How will this scale? What does year three look like?”
Enterprise deals must withstand internal review by a broader group of stakeholders. Champions and users are no longer the only decision makers. Pricing must make sense financially, operationally, and strategically. It must support a clear narrative that buyers can carry forward into their internal approval process.
Pricing and packaging influence whether:
Buyers perceive the solution as strategic
They understand the differences between tiers
They can justify the investment to internal stakeholders
Expansion happens naturally or feels forced
Procurement views the model as predictable and fair
When pricing friction appears, it usually has little to do with the number itself. Instead, it reflects issues with how value, packaging, and outcomes are communicated.
Where to Begin: Establish the Foundation Before You Price Anything
Effective pricing work begins by clarifying the problem you are trying to solve. Pricing is almost always a response to an underlying business challenge, not the challenge itself. Without this clarity, even well-structured pricing models will struggle. One of the first questions I ask is, “What exactly broke that made you say, ‘We need to revisit pricing’?”
Common triggers for pricing work include:
A new product or capability is being introduced
The current model no longer reflects how customers realize value
The portfolio has accumulated complexity that no longer makes sense
Sales relies heavily on custom deals or exceptions
Expansion is inconsistent or difficult to predict
Buyers struggle to understand tier differences
Value metrics no longer reflect usage patterns or outcomes
Once you understand why pricing is being revisited, the next step is to assess the value metric. The value metric determines how price scales with usage or outcomes. Good value metrics create transparency, predictability, and fairness for both the buyer and the provider. User-based pricing works in some contexts, but many enterprise SaaS products benefit from models based on consumption, volume, workflows, data, environments, or measurable outcomes. I’ve seen more than one company unlock expansion simply by aligning the metric to how customers already measure success internally.
Pricing initiatives that start with clarity about the ICP, the segmentation framework, and the correct value metric tend to produce durable, scalable models. The ones that skip straight to “What should the new price be?” almost never do.
What Information You Must Collect Before Evaluating Pricing Options
Pricing decisions require more than financial modeling. They require insight. Strong pricing work is grounded in four categories of inputs: internal data, external signals, customer insight, and product context. When any of these are missing, debate tends to fill the gap.
Internal Data
Internal data often reveals the most actionable signals. Discounting patterns can highlight where buyers perceive gaps. Heavy discounting usually indicates unclear packaging or an uncertain value narrative rather than a price that is objectively “too high.”
Feature usage also plays a critical role. If customers consistently ignore certain features, those features may not belong in the tier. If customers frequently hit usage ceilings, expansion may be constrained by the pricing structure rather than product value. Win and loss analysis reveals which narratives are working and which need reinforcement. I pay particular attention to deals that almost closed but stalled late; they often tell you more than clean wins or clear losses.
Synthesizing this information helps shape both pricing and packaging decisions.
External Signals
Competitor pricing should never dictate your model, but understanding the competitive context is important because buyers compare solutions. Procurement, in particular, evaluates tools through a comparative lens. Analyst reports, competitive packaging patterns, and review-site commentary all shape buyer expectations.
Your goal is not to match the competitive landscape. It is to make sure your model fits within the expectations that buyers naturally carry into evaluations and to understand where you are intentionally different. I’ve seen teams talk themselves out of a better model simply because it didn’t look like everyone else’s on the surface.
Customer and Buyer Insights
Customer insight is at the center of pricing work. Enterprise SaaS deals involve multiple stakeholders with different motivations and concerns. Champions focus on capability and workflow value. Economic buyers focus on outcomes and ROI. Procurement focuses on predictability, fairness, and risk mitigation.
Willingness to pay is not discovered by asking “What would you pay?” Instead, it is uncovered by understanding what outcomes matter most, how buyers justify software spend internally, what alternative solutions exist, and what creates internal friction. I listen carefully for the language buyers use when they talk about risk, budget, and trade-offs; those phrases usually show up again in internal approvals.
Product and Roadmap Context
Pricing must reflect where the product is going, not only where it is today. Roadmaps evolve. Capabilities mature. New modules emerge. Legacy features become irrelevant. When packaging falls out of sync with product strategy, sales teams struggle, and customer confusion increases.
Pricing decisions must reinforce the direction of the platform and create natural adoption and expansion paths. A model that made sense three years ago will quietly work against you if the product has evolved and pricing has not.
Gathering Willingness-to-Pay Feedback in Enterprise SaaS
Enterprise pricing research combines qualitative and quantitative methods. Each tool adds clarity when used correctly, and each has blind spots if used alone.
Van Westendorp helps establish price perception boundaries. Gabor-Granger highlights price sensitivity across discrete levels. Conjoint analysis reveals how buyers make trade-offs between features, bundles, and price. These can be powerful tools, but only when they are grounded in a strong understanding of your segments and buying committee.
However, the most valuable insights come from well-structured customer interviews. These conversations uncover how different stakeholders evaluate ROI, what they consider predictable or fair, how they prefer to allocate budgets, and what outcomes truly matter. Interviews also reveal the narratives buyers use internally, which directly influence how pricing should be framed. I’ve lost count of how many times a single phrasing from a customer interview ended up becoming the backbone of the pricing story.
Willingness to pay is context-specific. The goal is not to identify a perfect number. It is to understand the reasoning behind investment decisions: what feels like a stretch, what feels reasonable, and what feels suspiciously cheap for the value you claim to provide.
Pricing and Packaging for New Products or Major Releases
Pricing new enterprise capabilities is complex because teams often rush to assign a price before the value narrative is clear. I see this most often when a new module has created a lot of internal excitement; it’s easy to assume customers will see it the same way.
Introducing a new product requires clarity on several topics: how the new capability creates value, which segments will adopt it first, what measurable outcomes it supports, where it fits within the platform, how champions and economic buyers will justify the investment, and whether it represents new value or an extension of existing value.
One of the biggest decisions is whether the new capability belongs inside an existing tier, requires a new tier, or should be sold as an add-on. This decision depends on how transformative the capability is. If it materially changes outcomes or the customer’s operational workflow, it may warrant dedicated packaging. If it enhances existing functionality, it may be better positioned as part of an established tier.
Successful pricing for new capabilities begins with clarity around customer value rather than internal assumptions. When in doubt, I lean toward testing with a small group of design partners before committing to a broad model.
Pricing and Packaging for Existing Products
Repricing existing offerings is more challenging because customers have expectations, contractual rights, and workflows built around the current model. Yet, this is often where the greatest gains occur. Companies usually realize they need to reevaluate existing pricing when buyers show confusion, expansion slows, SKUs accumulate, or usage patterns no longer match the value metric.
The purpose of updating existing pricing is alignment. Realignment strengthens the connection between the product’s value and how revenue grows. In practice, this often looks like simplifying tiers, clarifying entitlements, and removing legacy decisions that seemed harmless at the time but accumulated into real friction.
Because existing customers have invested in your product, pricing changes in this area require transparency, thoughtful migration paths, and real empathy for how the change will land. When handled well, repricing can actually deepen trust by making the product easier to understand and the path to value more obvious.
SKU Rationalization
Enterprise SaaS companies often accumulate SKUs to solve short-term issues. Over time, this creates a portfolio that is difficult for customers and sales teams to navigate. I’ve seen sales teams with so many SKUs that they keep their own private cheat sheets just to quote accurately — which is usually a sign that something has gone too far.
SKU rationalization restores clarity by removing offerings that no longer support the strategic direction of the product or no longer reflect the value drivers customers rely on. The goal of SKU rationalization is coherence, not reduction for its own sake. A rationalized portfolio makes it easier to understand tiers, assign entitlements, and guide customers into the right package.
The side benefit is that internal teams breathe a little easier. RevOps, billing, support, and Product all move faster when they’re not carrying the weight of a decade’s worth of one-off decisions.
Sunsetting Products and Features
Sunsetting is one of the most sensitive parts of pricing work. Enterprise customers rely on stability. Abrupt changes undermine trust. I’ve watched relationships suffer not because a feature was removed, but because the way it was communicated felt rushed or dismissive of how customers depended on it.
Successful sunsetting requires transparency, early communication, logical migration paths, and a narrative that ties the decision to long-term customer benefit. Customers need to see that you’re not just cutting cost, you’re making room for a product that will be healthier and more focused.
When handled well, sunsetting strengthens trust rather than eroding it. It signals that you are willing to make hard decisions in service of building a better product over the long term.
Realigning Pricing with Modern Value Metrics
Value metrics that once worked may become misaligned as the product evolves. Moving from user-based pricing to consumption, workflows, data, or outcomes can unlock better expansion and reduce procurement friction. Buyers respond positively to pricing models that match how they measure success.
Modern enterprise products often require more nuanced metrics that reflect actual value creation. Pricing evolves as products mature. I’ve seen teams hold on to a legacy metric long after everyone agrees it no longer fits, simply because changing it feels daunting. The irony is that every month they wait, the technical and commercial debt gets a little bigger.
Operationalizing Pricing and Packaging Changes
Pricing changes require significant cross-functional coordination. Strategy is only the beginning. Execution determines whether the new model works in practice.
Operationalizing pricing requires updating CRM records, quoting tools, billing systems, compensation logic, legal templates, customer communication paths, documentation, and internal training. Customer-facing teams need clear narratives and confident understanding of why the change matters. If Sales and Customer Success are still “testing” how to explain the new model six weeks after launch, something was missed.
Pricing becomes real only when the entire revenue engine can execute it consistently. In my experience, teams almost always underestimate this part of the work the first time they do it.
Pricing Governance: Frequency, Planning, and Resourcing
Pricing is not a one-time decision. It is an ongoing discipline that must evolve as the product, market, and customer behavior evolve. The companies that do this well treat pricing like a product: it has owners, a roadmap, and regular checkpoints.
How Frequently Pricing and Packaging Should Be Evaluated
In practice, three layers of frequency work well.
An annual strategic review looks at value metrics, tier performance, competitive positioning, and product alignment. That review doesn’t automatically mean pricing changes every year, but it keeps the model anchored in reality rather than legacy assumptions. Your organization, your customers, and your competitive landscape are all evolving faster than ever. Where 18-month or even two-year reviews once felt acceptable, today you simply can’t afford to let pricing drift that long without a deliberate check-in.
Quarterly signal monitoring focuses on discount trends, win and loss patterns, feature usage, expansion behavior, and buyer objections. These indicators reveal whether friction is beginning to emerge before it shows up in churn.
Finally, event-based triggers matter. Pricing should be reassessed when major events occur, including roadmap shifts, new ICP definitions, platform rearchitecture, competitive moves, or significant changes in procurement expectations.
How to Structure a Pricing Project Plan
My experience with pricing project plans is that the tactical elements can quickly surpass 150 individual tasks—far more than most teams expect at the outset. Despite that level of detail, the work almost always unfolds within six core phases:
Discovery and alignment
Data collection and research
Modeling and scenario development
Cross-functional validation
Operational readiness and enablement
Rollout and monitoring
Each phase builds toward clarity and predictable execution. When teams try to jump straight from “We should change pricing” to “Let’s update the website,” they inevitably find themselves circling back to the steps they skipped—usually under more pressure, with less time, and with far higher stakes.
How Much Time to Allocate
A comprehensive enterprise pricing initiative typically spans 12 to 18 weeks:
Discovery and research: 3 to 4 weeks
Modeling and recommendations: 3 to 4 weeks
Cross-functional validation: 2 to 3 weeks
Operational readiness: 4 to 6 weeks
Shortened timelines often result in misalignment and long-term pricing debt. I’ve yet to see a rushed pricing project that didn’t create cleanup work down the road.
Where Pricing Should Live
Pricing should be cross-functional. Finance contributes essential financial perspective, but Product Marketing is often the best function to lead because pricing is ultimately a value narrative that connects product, market, and customer outcomes. Revenue operations, product, sales leadership, customer success, and legal all play key roles.
The important part is not which department owns pricing on an org chart; it’s that someone is clearly accountable, and the right voices are consistently involved.
Rollout: Controlled, Phased, and Measured
Pricing changes should not be introduced universally at once. Phased rollouts, early-adopter cohorts, and controlled experiments reduce the risk of major disruption. Testing the new model with a subset of customers or a specific segment allows time to refine messaging, operations, and customer guidance.
I’ve found that even one carefully chosen pilot segment can surface operational edge cases and language issues that would have become much bigger problems if the change had gone live everywhere at once.
Measuring Whether Your Pricing Strategy Is Working
Pricing impact appears through both leading and lagging indicators. Early signs include improved deal velocity, reduced discounting, clearer customer comprehension, and stronger internal confidence. Longer-term indicators include higher expansion revenue, stronger net revenue retention, improved profitability, and reduced negotiation friction.
If nothing changes — if the same discount habits remain, if conversations still stall in the same places, if expansion continues to be ad hoc — then the pricing model didn’t solve the real problem. In that situation, I go back to the foundation: segmentation, value metric, and narrative.
Avoiding Common Pricing Mistakes
I’ve made some of these mistakes myself, and I’ve watched dozens of teams repeat them. The biggest ones:
Treating pricing as a one-time project guarantees misalignment within a year. It turns pricing into a fire drill instead of a managed capability.
Adding SKUs without a strategy solves a short-term problem but creates long-term chaos. It’s one of the fastest ways to confuse both your customers and your own team.
Underpricing strategic capabilities sends the wrong signal about value. If you treat your differentiators like add-ons, buyers will too.
Using the wrong value metric is one of the fastest paths to churn and unpredictable expansion. When the metric fights how customers work, they eventually push back.
Rushing rollout without operational readiness undermines even the best strategy. If your systems and teams are not ready, your customers will feel that instability immediately.
Basing decisions on internal opinions instead of customer insight is the quiet killer of pricing work. It often feels efficient in the moment, but it rarely holds up once the model hits real deals.
Avoiding these requires discipline, honesty, and ongoing governance. There is no shortcut around that.
The Path Forward
Pricing and packaging should create clarity for your team and for your customers. They should reflect how value is created and how customers grow. They should support expansion, guide customers into the right tier, and reinforce the direction of the product.
Most SaaS companies have the insight they need. What they lack is a structure for turning that insight into a durable, trusted pricing system.
If you’re working through pricing and packaging in preparation for 2026, I hope these lessons help you avoid friction and build something that truly supports long-term growth.
BlindSpot helps SaaS companies build pricing systems designed for scale, grounded in customer value, informed by insight, and executable across every function.
If you’re ready to get pricing and packaging right, let’s talk.
