Pricing strategy is one of the most frequently debated parts of building a business — and for good reason. No matter what you're selling or which industry you’re in, deciding what to charge can quickly become one of the toughest and most critical choices you'll make. 

And even though there’s no shortage of content and opinions about pricing, that abundance can actually make it harder. Many businesses still fall into the same traps while searching for the ideal price point that can effectively boost their profits.  

So, how can you tell if your pricing strategy is off-track? Here are a few signs to look out for: 

You’re Not Losing Deals Because of Price 

Sounds like a win, right? It’s not. 

If every potential customer is saying yes without pushback, it usually means one thing: you’re priced too low. Great products with real value usually get some resistance. In fact, 10-15% price objections are healthy. It means you’re sitting near the top of your perceived value band — exactly where you want to be. 

You’re Selling to the Wrong Persona — and Don’t Realize It 

One of the most under-discussed pricing issues isn’t the number — it’s who you’re selling to. 

We’ve seen founders build amazing tools for senior operators… and then price them like they’re selling to interns. Or worse, position a premium SaaS product for budget-conscious small businesses when it’s actually built for mid-market teams drowning in inefficiencies. 

Hard-to-Google insight: In a 2023 founder roundtable we attended, a founder of a B2B healthtech product tripled their ACV (Annual Contract Value) by doing one thing: they moved their pitch up the org chart. Same product. Higher-stakes buyer. Better pricing power. 

If your price feels too high to your current audience, maybe you’re not overpriced — maybe you’re talking to the wrong crowd. 

You’re Pricing Based on Cost, Not Transformation 

You’ve probably heard this before. But let’s go deeper. 

Cost-plus pricing (taking your cost and adding a margin) is not just outdated — it’s dangerous. Because it ignores your customer's reality. 

What transformation does your product create — and what is that worth? 

If you’re building a tool that saves a COO 10 hours a week, that’s not worth $49/month. That’s worth a decision-maker’s peace of mind. Price for that. 

Founder insight: One early-stage productivity startup we work with tried 3 price points: $15, $39, and $89. The $89 tier — with just one extra premium feature — outsold the rest by 40%. Why? Because it spoke directly to “time-starved execs” instead of individual freelancers. 

Your Prospects Keep Asking Questions Like “So What Exactly Do I Get?” 

Confusion kills conversions. 

If customers keep circling back to understand what they’re paying for, it’s not a product problem. It’s a messaging and pricing alignment problem. 

Your pricing should instantly tell a story — not just of what they get, but what they’ll achieve. Features are the “what.” Outcomes are the “why.” Lead with the why. 

You Haven’t Changed Your Pricing in Over 6 Months 

Early-stage pricing is like code. If it’s not being updated, it’s probably broken. 

Big companies can go a year without a pricing change. Startups? Not a chance. You’re still learning who your customer really is, what they’re willing to pay, and how your product fits into their day. 

If you’ve never run a pricing experiment — like testing a higher anchor price, bundling features differently, or A/B testing value-based messaging — you’re flying blind. 

Types of Pricing Strategies 

Now that we’ve discussed how to identify whether your pricing strategy is working, let’s explore different pricing strategies to consider, each with its own advantages and applications. 

1. Penetration Pricing 
This strategy involves setting a low initial price to quickly attract customers and gain market share. It’s especially effective for new entrants looking to establish themselves in the market. 

Example: Streaming platforms offering discounted subscription rates for the first few months to quickly grow their user base. 

2. Price Skimming 
With price skimming, you start with a high price and gradually lower it over time. This works best for products that are innovative or in high demand early on. 

Example: New smartphones are often launched at a high price, with gradual discounts over time as newer models are released. 

3. Value-Based Pricing 
In this approach, you set prices based on the perceived value to the customer, rather than on production costs. This is perfect for unique products or services that deliver significant value. 

Example: Luxury brands like Rolex or Louis Vuitton set their prices based on their prestige and the perceived value of their products. 

4. Competitive Pricing 
Here, you set your prices in relation to competitors' rates. This strategy is common in industries where products are similar and highly competitive. 

Example: Supermarkets pricing staple items like milk or bread to stay competitive with other stores in the area. 

5. Premium Pricing 
Premium pricing involves charging a higher price to reflect a product’s superior quality or exclusivity. It’s ideal for high-end products that target customers willing to pay more for the best. 

Example: Brands like Apple or Tesla use premium pricing to signal their products’ high quality and innovation. 

6. Economy Pricing 
This strategy offers basic, no-frills products at a low price, making them accessible to a budget-conscious audience. It’s commonly used in mass-market industries. 

Example: Budget airlines like Ryanair focus on low-cost, no-frills services to attract price-sensitive travelers. 

7. Bundle Pricing 
Bundle pricing involves grouping several products together and selling them at a discounted rate. This strategy can increase sales volume by offering more value to customers. 

Example: Cable providers offering bundled packages that include TV, internet, and phone services at a discount. 

8. Price Leadership 
Price leadership occurs when a dominant company in an industry sets the price for products or services, and competitors follow suit. 

Example: OPEC, by adjusting oil production levels, influences global oil prices, and other countries follow suit. 

9. Preemptive Pricing 
Preemptive pricing is designed to prevent competitors from entering the market or to push them out by offering products at lower-than-market prices temporarily. 

Example: When Amazon first launched the Kindle, it priced the e-books below typical hardcover book prices to dominate the market early on. 

Pricing Is Not a Math Problem — It’s a Perception Game 

Most pricing mistakes don’t come from bad math — they come from bad assumptions. About your audience. Your value. And yourself. 

If you’re still in the early days of building, launching, or growing your startup, now is the time to rethink your pricing like it’s a strategic asset — not just a number you have to settle on. 

Listen closely. Test often.  
And never forget that the right price doesn’t just close deals — it tells the world how seriously to take you.