SaaS Pricing Optimization: The Price Setting Challenge | Krzysztof Szyszkiewicz S5:E11

Written by Mike J Midgley | Sep 30, 2025 8:31:32 AM

Welcome to Part 2 of our SaaS Pricing Optimization series on the Force & Friction Podcast, where we break down what really moves the needle in GTM, RevOps, AI, partnerships, and SaaS growth.

Today, we're tackling "The Price Setting Challenge" with Krzysztof Szyszkiewicz, founder of Valueships and one of the world's leading SaaS pricing consultants.

If you haven't watched Part 1: The Value Challenge, we recommend starting there as this series builds momentum across all three episodes.

This second installment focuses on why you're probably selling yourself short, a bold claim backed by shocking data from Krzysztof's consulting practice.

What makes this episode particularly eye-opening is Krzysztof's revelation that in 90-95% of their last 100 client engagements, they decided to increase the average price.

This isn't coincidence, it's systematic underpricing driven by two critical factors: founders who don't want price to be a barrier between customers and their product, and companies treating pricing as a one-off task rather than a strategic process.

We explore the Van Westendorp price sensitivity meter, the four-quadrant feature matrix that reveals why most SaaS companies are losing margin on premium buyers and conversion on budget buyers, and the car analogy that transforms how you think about feature packaging.

Krzysztof Szyszkiewicz

Krzysztof is a certified expert in price, revenue and margin management who specializes in empowering digital companies, including SaaS, e-commerce, and B2B to maximize their revenue through innovative pricing and strategy.

As Partner & Co-founder of Valueships, he's passionate about driving topline growth and unlocking full revenue potential for companies that know there's more money on the table.

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Here are the core areas we discuss in today's episode:

1. The 90-95% Problem: Why Most SaaS Companies Systematically Underprice

Krzysztof opens with a shocking statistic from his consulting practice that reveals the scope of the underpricing epidemic.

"For the last 100 client engagements we were in, in 90-95% of the cases, we decided to increase the average price... And what does it mean, there are two things behind it."

He identifies two root causes: founders who are so invested in their product that they don't want price to be a wall between customers and their solution, and companies treating pricing as an ad hoc financial fix rather than a value-driven process. This systematic underpricing costs companies millions in lost revenue.

2. From One-Off Task to Strategic Process: The Pricing Transformation

Krzysztof challenges the fundamental misconception about how pricing should be managed within SaaS organizations.

"That we treat pricing, as a one-off task that we should do every now and then, and most likely it will be unpleasant. What I would love to see about pricing is to put a price process as one of the inputs to your top line growth."

This shift from reactive pricing changes every 3-4 years to proactive annual pricing processes puts companies in the top one percentile of pricing advancement, unlocking the full power of pricing as a growth lever.

3. The Van Westendorp Price Sensitivity Meter: Research-Driven Pricing

Krzysztof introduces the scientific approach to understanding customer price sensitivity through four critical questions.

"So the first question goes,
1: At what price would you consider the product starting to get expensive?
2: At what price would you consider the product to be a bargain, great buy for money?

3: At what price would you consider the product to be so expensive that you would not consider buying it?

4: At what price would you consider the product to be priced so low that you would feel the quality couldn't be very good?"

This framework reveals that markets contain premium buyers, normal buyers, and budget-conscious buyers with different price sensitivities—and most companies are losing margin on premium buyers while losing conversion on budget buyers.

4. The Four-Quadrant Feature Matrix: Core, Differentiable, Add-On, and Trash Land

Krzysztof reveals the car analogy that transforms how SaaS companies should think about feature packaging and pricing.

"Think of it in terms of a car, think of it as an alarm in the car, so, the alarm in the car is the feature that everyone would like to have... Nevertheless, cars do not differentiate themselves through the alarms, they differentiate themselves through engines. An engine in a car is a type of a feature with high preference and high willingness to pay."

The framework categorizes features into core features
1: Alarm - everyone expects them

2: Differentiable features (engine - high preference and willingness to pay),
3: Add-on features (leather seats - low preference but high willingness to pay),
4: Trash land features (undercarriage - necessary but not promotional).

This reveals why 60-70% of clients have differentiable features in their cheapest plan, killing upsell potential.

5. The Testing and Migration Strategy: Solving the Over-Engineering Problem

Krzysztof addresses the critical challenge of companies that have over-engineered their basic plans and need to restructure without losing customers.

"Most people are falling into the trap of thinking about pricing as a one-off solution rather than a process. So, first step is to downsize your cheapest plan, if you think that you are giving too much, and then launch it only for the new users. If you see that for new users, it works, they are scoring on the higher RPO, then deciding on your financials, you can decide to increase the prices to currently existing users."

His systematic approach includes testing different migration strategies: grandfathering with time limits, paid upgrades to maintain features, or forced migrations to appropriate plans. The key is treating this as an ongoing process rather than a one-time fix.

Final Thoughts

Krzysztof leaves us with a simple diagnostic framework for identifying underpricing.

"IIt screams of underpricing, first of all, you haven't increased your price for a couple of years, more than a year, or, if most of your clients are just converting on the biggest plan, and they are not using all of the features, and for some reason they are not churning."

His final insight emphasizes the power of the car analogy exercise: take 10 features, categorize them using the car framework, and you'll discover that internal teams understand features very differently—the first step in a beautiful pricing journey that transforms pricing from a painful task into a strategic process.

About This Series

This is Part 2 of our comprehensive three-part SaaS Pricing Optimization series with Krzysztof Szyszkiewicz. Each episode tackles a specific pricing challenge that's costing SaaS companies millions in lost revenue:

Each episode tackles a specific pricing challenge that's costing SaaS companies millions in lost revenue:

• Part 1: The Value Challenge - Why companies hide their value and how to communicate profit effectively.

• Part 2: The Price Setting Challenge (This Episode) - How to set prices based on willingness to pay rather than guesswork.

• Part 3: The Discounting Challenge - Why discounting is killing margins and how to optimize realized prices.

Don't miss Part 3 where we'll reveal exactly how much revenue is leaking through discounting, including one particular statistic about how much more you need to sell to recover from specific discount levels that will fundamentally change how you think about pricing negotiations.

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Mike Midgley runs a portfolio career, a dynamic hands on digital entrepreneur, founder of the Scrubbing Squad, NXD, strategist, public speaker, Winning by Design certified Revenue Architect and Host at The Force & Friction Podcast.

Mike has achieved multiple exits over a 30+ year career, raised Venture Capital and franchised his businesses 68 times.

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