7 pricing lessons from my conversation with We Are Sales

I recently had a conversation with Dylan Mendes of We Are Sales about pricing strategy. Seven things came up that I see repeated across almost every scaling company I work with.

1. Underpricing costs you deals

This is counterintuitive. Most founders think lower prices make it easier to sell. But in enterprise B2B, the opposite is often true.

I have seen situations where pricing 10x higher actually improved sales performance. Enterprise clients want vendors they believe will remain solvent. If your product is critical to their operations, a price that is too low signals risk. They start wondering: can this company actually sustain this?

Pricing is not just about affordability. It is about confidence.

2. Strategic packaging reduces sales cycles

One of my clients had a product with 50 technical features. Impressive, but impossible to sell efficiently. Every deal required a custom demo walking through everything, and prospects still could not figure out what they needed.

We reorganized those 50 features into 9 targeted pricing tiers, segmented by customer type and use case. The result: sales cycles dropped from 12 to 18 months down to 6 to 9 months. Not because the product changed, but because the packaging made it easier to qualify and decide.

Good packaging is a sales accelerator.

3. Establish value before discussing price

Too many sales conversations start with the price page. “Here is what we charge” followed by a features list.

The better approach is to demonstrate business outcomes first. What does the customer actually achieve with your product? Then position pricing based on where they are in their journey. A customer just starting out has different willingness to pay than one who has been using you for two years and depends on you for core operations.

Value first, price second. Always.

4. Do not mirror competitor pricing

This is one of the most common traps. You look at what competitors charge and match it, maybe with a small discount.

The problem: your competitors have different cost structures, different go-to-market strategies, and different business objectives. Their pricing reflects their context, not yours.

By all means, analyze their tier structure. It tells you something about how they think about segmentation. But copying their price points misses the opportunity to differentiate. Your pricing should reflect your value, not theirs.

5. Market reality beats theory

I had a client who developed a new pricing model that was objectively better for their customers. Mathematically, it offered 30% savings compared to the old model.

Their legacy customers rejected it. The reason had nothing to do with the numbers. These customers had built their annual budgets around predictable pricing. They preferred the certainty of what they knew over the theoretical savings of something new.

Pricing changes do not happen in a vacuum. They happen in the context of real organizations with real budgets, real procurement processes, and real human resistance to change.

6. Discount with structure, not with hesitation

Discounting is not inherently bad. Bad discounting is bad. The difference is whether you are discounting from a position of confidence and structure, or from a position of uncertainty and desperation.

Good discounting looks like this: structured programs available to every customer equally. Upgrade to premium this year, get 15% off. Volume commitment of three years, get a better rate. Clear, predictable, fair.

Bad discounting looks like this: the sales rep nervously offers 20% off because the deal is stalling, then adds another 10% when the prospect hesitates, then asks their manager for a special approval. No structure, no consistency, no integrity.

7. Include product leadership in pricing decisions

Pricing is not a sales-only conversation. It is not a finance-only conversation. It requires cross-functional alignment between sales, marketing, and product.

Product owners are accountable for value delivery. If they are not involved in pricing decisions, you get a disconnect between what the product does and what the price reflects. Sales starts discounting features that product spent months building. Marketing positions the product differently from how it is priced.

The best pricing decisions happen when product leadership is at the table.

These are not abstract principles. They come up in nearly every engagement I do. If you want to explore how they apply to your situation, book a conversation.