Sales & Conversion
Personas
SaaS & Startup
Time to ROI
Medium-term (3-6 months)
Last year, I watched a SaaS founder agonize over his pricing page for three weeks. Three weeks! He kept moving numbers around, adding features, removing features, creating a "Pro Plus Ultra" tier that nobody asked for.
Meanwhile, his competitor launched with dead simple pricing and started eating his lunch.
Here's the thing about pricing tiers that most founders get wrong: you're not building a menu at a fancy restaurant. You're not trying to showcase every possible feature combination. You're trying to make one thing crystal clear - which option gets your customer the result they want, fastest.
After working with dozens of SaaS clients on their pricing strategies, I've seen what actually converts versus what looks impressive in a deck. And spoiler alert: the "best practices" everyone preaches? They're often completely backwards.
Here's what you'll learn from my real-world experiments:
Why the "freemium trap" kills more startups than it helps
The psychological pricing anchors that actually work (not the textbook ones)
How I helped clients 2x revenue by removing features, not adding them
The pricing page structure that converts cold traffic
When to use 2 tiers vs 3 tiers (and why 4+ is usually a mistake)
This isn't theory from a pricing consultant who's never run a business. This is what I learned helping real companies fix their broken pricing - including the failures that taught me more than the successes.
Industry Reality
What everyone tells you about pricing tiers
Walk into any SaaS conference or scroll through any "growth hack" thread, and you'll hear the same pricing gospel repeated like scripture:
"Use the Rule of Three" - Always have exactly three tiers because of psychological anchoring. Make the middle one look like the obvious choice. Price the top tier high to make the middle look reasonable.
"Load up the Premium" - Stuff your highest tier with every feature you can think of. The more value you pack in, the better the deal looks.
"Start with Freemium" - Give away your core product for free to build a user base, then upsell them later. It worked for Slack and Zoom, so it'll work for you.
"Test Everything" - A/B test different price points until you find the magic number. Run multivariate tests on feature combinations. Optimize, optimize, optimize.
"Follow the Leaders" - Look at what successful companies in your space are charging and price accordingly. If they're doing it, it must work.
This advice exists because it's easy to measure, sounds sophisticated, and gives founders a framework to follow when they're drowning in decisions. Plus, there are enough success stories to make each approach seem validated.
The problem? Most founders who follow this playbook end up with pricing pages that convert like landing pages for tax software - technically correct but completely soulless. They optimize for metrics that don't matter while ignoring the psychology that actually drives purchasing decisions.
Here's what the "experts" don't tell you: your pricing strategy isn't about your tiers. It's about your customers' relationship with value and their tolerance for risk. Get that wrong, and no amount of A/B testing will save you.
Consider me as your business complice.
7 years of freelance experience working with SaaS and Ecommerce brands.
Let me tell you about the client that taught me everything I know about pricing psychology - by doing almost everything wrong first.
I was working with a B2B SaaS that helped restaurants manage inventory. Smart founder, solid product, but they were bleeding money on customer acquisition. Their free trial was converting at maybe 2%, and most paying customers churned after three months.
When I audited their setup, I found a pricing page that looked like it was designed by committee. Four tiers, ranging from "Starter" at $29/month to "Enterprise" at $299/month. Each tier had a laundry list of features, with checkmarks scattered across a comparison table that required a PhD to decode.
The founder was convinced they needed all four tiers to "serve different market segments." The free trial was positioned as the entry point to build trust. Everything looked textbook perfect.
But here's what was actually happening: prospects were landing on the pricing page, getting overwhelmed by choices, and leaving to "think about it." The few who did sign up for the free trial barely used the product because they couldn't figure out which features they actually needed.
The first experiment I suggested nearly gave him a heart attack.
I wanted to kill the free trial entirely and offer just two paid options: "Standard" at $97/month and "Pro" at $197/month. No free tier. No "Starter" option. No "Enterprise" with features nobody used.
"You're going to kill our conversion rate," he said. "People won't pay without trying it first."
That's when I explained something that most SaaS founders don't understand: the people who won't pay upfront are usually the people who won't pay later either. Free trials often attract tire-kickers, not serious buyers.
The real problem wasn't the price point - it was that we were optimizing for the wrong conversion event. Instead of optimizing for trial signups, we needed to optimize for qualified leads who were ready to solve a real problem.
Here's my playbook
What I ended up doing and the results.
Here's the systematic approach I developed after fixing pricing for dozens of SaaS companies. This isn't theory - it's the exact process that helped my restaurant client increase their average deal size by 180% while improving trial-to-paid conversion.
Step 1: Start with Customer Jobs, Not Features
Forget about your feature list for a minute. Instead, identify the 2-3 core "jobs" your customers are hiring your product to do. For the restaurant client, it wasn't "inventory management" - it was "stop losing money on waste" and "never run out of popular items."
I spent two weeks interviewing their best customers. The breakthrough question: "What would happen to your business if you stopped using our product tomorrow?" The answers revealed the real value drivers, not the features they used most.
Step 2: Design Around Decision Psychology
Most pricing pages are designed around features. I design around customer psychology. Here's the framework:
• The "Safe Choice" - One tier positioned as the obvious, no-brainer option for your core audience
• The "Ambitious Choice" - A higher tier for customers who want more growth/scale/capability
• That's it. Two tiers maximum for most businesses
For the restaurant client, "Standard" solved the waste problem for single locations. "Pro" was for multi-location owners who needed centralized reporting. Clean, simple, no confusion about which tier to choose.
Step 3: Price for Commitment, Not Affordability
Here's the counterintuitive part: I often recommend raising prices, not lowering them. Why? Because the right customers will pay more for a solution they're committed to using.
We moved the restaurant client from $29-299 pricing to $97-197. Revenue per customer nearly doubled, but more importantly, customers who paid $97 were infinitely more engaged than customers who paid $29. They showed up to onboarding calls. They used the product daily. They renewed.
Step 4: The "Anti-Freemium" Strategy
Instead of a free trial, we implemented what I call "qualified demos." Prospects could book a 30-minute session where we'd customize the product with their actual data and show real ROI calculations based on their business.
This did two things: it filtered out unqualified leads who weren't ready to pay, and it demonstrated value using their specific context. No more generic demos or tire-kickers.
Step 5: Test the Whole Experience, Not Just Price
Rather than A/B testing price points, we tested entire customer journeys. Different landing pages, different discovery processes, different ways of presenting value. The pricing page was just one piece of a larger conversion system.
The winning combination: a problem-focused landing page that led to a qualification survey, followed by a custom demo, then a simple two-tier pricing choice. Total conversion from visitor to paying customer: 12% (up from 2%).
Value Alignment
Matching tiers to customer psychology not features
Customer Psychology,Understanding what drives purchase decisions beyond features
ROI Calculation
Building pricing around measurable business outcomes
Qualification Process,Filtering for committed customers before they see pricing
Testing Framework
Optimizing the entire journey not just price points
The results spoke for themselves, but not in the way most people expect from a "pricing optimization" case study.
Conversion Metrics:
• Visitor-to-trial conversion dropped from 8% to 4% (we were attracting fewer but better prospects)
• Trial-to-paid conversion jumped from 2% to 12%
• Overall visitor-to-customer conversion increased by 180%
Revenue Impact:
• Average deal size increased from $47/month to $134/month
• Customer lifetime value improved by 240% due to lower churn
• Monthly recurring revenue grew 320% within six months
But here's what really mattered: customer satisfaction scores went up, not down. When people pay more for something they're committed to using, they actually get better results and stay longer.
The qualification process meant we were only talking to restaurant owners who had real pain around inventory waste. The higher price point meant they were invested in making the product work. The simplified tiers meant they could make decisions quickly without analysis paralysis.
Six months later, the founder told me it was the best business decision he'd ever made. Not because of the revenue increase, but because he finally had customers who wanted to be there.
What I've learned and the mistakes I've made.
Sharing so you don't make them.
1. Confusion kills more deals than price
I've never seen a pricing page fail because it was too expensive. I've seen hundreds fail because prospects couldn't figure out which option was right for them. Clarity beats optimization every time.
2. Free trials attract the wrong customers
People who won't pay $97 upfront usually won't pay $97 after a trial either. Free trials often just delay the "no" while wasting your onboarding resources on unqualified prospects.
3. Features don't sell, outcomes do
Nobody cares about your "advanced analytics dashboard." They care about "never running out of their best-selling item again." Price your tiers around the outcomes customers actually want.
4. Higher prices create better customers
Customers who pay more are more engaged, provide better feedback, and stay longer. They're also more willing to refer others. Don't race to the bottom on price.
5. The pricing page is the last place to optimize
Fix your targeting, your messaging, and your qualification process first. If you're attracting the wrong prospects, no pricing strategy will save you.
6. Test journeys, not just prices
A/B testing price points in isolation is like optimizing the color of a button on a broken page. Test the entire customer experience from first touch to purchase decision.
7. Two tiers beat three tiers for most businesses
The "rule of three" works for restaurants, not SaaS. Give customers a clear "good" and "better" choice, then make the recommendation obvious based on their situation.
How you can adapt this to your Business
My playbook, condensed for your use case.
For your SaaS / Startup
For SaaS startups, focus on these key areas:
Start with just 2 tiers - Avoid the complexity trap
Price around customer jobs - Not feature lists
Qualify before pricing - Use discovery calls or surveys
Test the whole journey - Landing page to purchase
For your Ecommerce store
For ecommerce businesses, adapt these principles:
Bundle by customer intent - "Starter kit" vs "Complete solution"
Use outcome-based naming - "Get started" vs "Scale faster"
Offer consultation tiers - Basic vs premium support levels
Test with qualified traffic - Don't optimize for bargain hunters