Mastering Willingness to Pay

The most valuable conversations you'll ever have

Foreword from Gaurav Vohra

I navigated willingness to pay for Superhuman many years ago.

We did something remarkable. We established a premium price point for a product that had always been free. But getting there wasn’t easy.

I studied Van Westendorp. I read conjoint papers. I stumbled through conversations.

I wished for a simple guide.

This essay is that. What follows is the clearest explanation of willingness to pay I’ve seen. Every founder should internalize it.

This is a guest post from Fynn Glover, Founder & CEO of Schematic, from his pricing & packaging book: You’re Leaving Money on the Table.

To get the full book, click here (online) or click here (print).

Mastering Willingness to Pay
from You’re Leaving Money on the Table
by fynn glover

After selling my first company — where, for full disclosure, I’d botched pricing and packaging — I was charged with leading pricing at a high-growth cyber company.

This gave me the opportunity to meet James Wood, who ran Insight’s Center of Excellence on pricing.

I learned a lot, but most importantly, I learned different approaches to conducting primary research on customer willingness to pay.

I believe that being able to talk to customers about willingness to pay is arguably the single most important tool in a founder’s toolbelt for finding PMF.

I also believe that conducting these conversations should never stop.

They should occur when you’re pre-product, after you’ve won initial customers, and then on an ongoing basis as you extend and deepen your PMF.

Before leaving the cyber company to start Schematic, I did dozens of WTP interviews to prove to myself the market would pay for the solution we envisioned.

When enough people confirmed WTP, I felt confident enough to go out and raise money and leave the good gig.

Over the years, I’ve done countless WTP interviews with customers.

But I’ve also trained hundreds of founders on WTP so that they are armed with the vocabulary of pricing and packaging and are therefore confident in their ability to position and sell their pricing.

This has evolved into daily Pricing Therapy: live, 30-minute conversations where I help founders learn the vocabulary of willingness to pay and, just as importantly, pressure-test their confidence in their own pricing narrative.

What I often find with early-stage founders is that a lack of confidence is the default state.

As Xano founder & CEO Prakash Chandran puts it,

“almost 100% of founders undervalue themselves... especially initially. You’re like, ‘please, will you pay me money for this? Like any money, like, can you give me $5 for it, please?’”

He’s right.

We so often set our first price from a place of desperation, and then, as he says, we’re “so scared” that “everyone is going to leave” that we never touch it again.

My “therapy” sessions with early-stage founders attempt to work through this fear.

It’s part therapy, part Socratic method, and part design exercise. What happens in those calls says more about a founder’s confidence in their value than any other exercise I’ve seen.

A Real Session

(The following story is drawn from an anonymized Pricing Therapy session with a company we’ll call “AdOptics” — a fast-growing ad-tech platform in the DTC e-commerce space.)

AdOptics had built something powerful: software that automatically stops brands from wasting ad dollars on non-incremental audiences.

It was delivering 30–40 percent improvements in customer-acquisition cost. On paper, an easy sell.

In practice, their founder — Alex — was frustrated. He’d gone through three pricing models and none felt right.

He told me:

“In ad tech, we look expensive to SaaS buyers and cheap to performance marketers.

We started at five to ten percent of saved ad spend — ROI-based and fair — but it was impossible to explain.

Then we went with one percent of ad spend — too unpredictable for CFOs.

Now we’ve landed on static tiers.

It works, but it’s finger-in-the-wind.”

He looked tired.

Pricing fatigue is real.

I asked him to role-play.

“Pretend I’m your dream customer. I ask, ‘Hey Alex, can you explain your pricing?’ Walk me through exactly what you’d say.”

He delivered his pitch — a clear explanation of tiered pricing tied to ad spend — then paused.

“Grade yourself,” I said. “How’d that feel?”

“B minus,” he answered.

“I know it should be shorter and more about value, but the math is hard to explain.”

“Okay,” I asked, “now put yourself in your customer’s seat. How do they feel hearing that?”

“Sticker shock. They’ve never seen a SaaS tool at six or seven grand a month. Even if it’s positive ROI, it feels foreign.”

We talked about what would make a customer excited to pay more next year.

Alex didn’t hesitate:

“If they cut acquisition cost forty percent and lift profit sixty, they’d happily pay ten grand.”

He knew the value; he just hadn’t built the story around it.

From there, the conversation shifted from price level to value.

I asked about value metrics:

“Is CAC your customers’ single north-star metric when they purchase your product, or are there others?”

“Mostly CAC,” he said. “Sometimes NCAC — new customer acquisition cost — but same idea.”

That’s when we got to the heart of it:

“You have a clear value metric — ad spend reduced, or CAC improved — but you’re forcing that value through a single lens: percent of ad spend.

What if you built a hybrid model? A base platform fee plus a performance-linked variable? Predictable for the CFO, scalable for you.”

His eyes lit up.

“That would actually calm the sticker shock. Two thousand base, plus usage or performance on top. Makes sense.”

Exactly. The session wasn’t about discovering the “perfect” price.

It was about aligning architecture, psychology, and confidence.

By the end, Alex said something every founder eventually says in these calls:

“I feel like I can finally explain it without tripping over myself.”

Why These Conversations Matter

One of the most important things to understand about pricing is that it is a communication discipline.

The way you talk about price — the language, metaphors, and structure — shapes how customers perceive value long before they ever see a proposal.

Try to surface three things:

1. Clarity: Do you understand what value you create and how to express it?

2. Confidence: Can you deliver your price narrative with confidence, poise, and persuasion?

3. Consistency: Does every team inside your company tell the same story?

If those aren’t aligned, the model doesn’t matter.

You’ll lose deals, underprice, or discount out of insecurity.

The Playbook: Eight Steps to Discover Willingness to Pay

Over time, I distilled these sessions into a repeatable flow.

It isn’t statistical; it’s conversational.

You can run it with customers, prospects, or design partners in under an hour.

1. Context & Framing: Explain your product’s promise. Get the buyer in the right mental model.

2. Perceived Value: Ask what problems they think it solves, and which features feel indispensable.

3. Relative Value: Compare your value to the tools they already pay for. If they spend $100K/yr on Salesforce and think your product is 50% as valuable, they’re indicating that they’d value your product at ~$50K/yr.

4. Price Metric: Explore which metric best maps to their perceived value — seats, usage, API calls, customers, etc.

5. Packaging Schema: Show draft tiers (Good/Better/Best). Ask what resonates and what feels off.

6. Maximum WTP: Either open-ended (“What’s the max you’d pay?”) or scenario-based (“At $X, what happens?”).

7. Influence Drivers: Uncover the real factors — budget, comparables, frequency, stakeholder buy-in.

8. Feedback & Emotion: End by asking how the conversation felt. You’re listening for discomfort, not just answers.

The power of this framework is its simplicity.

It requires curiosity and empathy.

You’re teaching customers and yourself to talk about value together without flinching.

Sidebar: When Van Westendorp or Conjoint Make Sense — And When They Don’t

I think Van Westendorp is a good tool when you’re selling a simple product with a single price point, and you want a quick read on perceived expensiveness.

It’s fast and directional.

But it doesn’t capture usage, value metrics, hybrid pricing, or real buyer psychology.

I think conjoint analysis is a good tool when you have a large statistical sample size, well-defined packaging options, and the time and budget to run a proper survey.

It can quantify tradeoffs across bundles — but only when your product and customer base are mature enough to support it.

For most founders and product leaders in high-growth companies, I’ve found this eight-question framework to be far more useful.

It helps you understand how customers think about the value you create relative to other tools, how they would intuitively think about & measure your value, how packaging would influence their decision, how sensitive they are to price, and what constraints — budget, internal politics, reputation — actually drive their willingness to pay.

This isn’t statistical.

It’s behavioral, practical, and grounded in real conversations with real buyers — which is what most startups need.

The Founder’s Psychology

What surprised me most after running hundreds of sessions is how much pricing anxiety mirrors founder psychology.

A founder who underprices often under-believes.

A founder who over-complexifies is usually compensating for insecurity.

As pricing expert Kris Szyszkiewicz puts it,

“I thought at the very beginning the pricing is 90% analytics... 10% confidence.

I wouldn’t stay by this statement anymore. It’s like more of a 50-50.”

And the best founders — the ones who can explain their price clearly, calmly, and consistently — project a kind of gravity that customers feel.

They aren’t guessing. They’re teaching.

In that sense, willingness to pay is reciprocal.

Customers mirror your confidence.

If you hesitate, they sense risk.

If you explain with conviction, they assume value.

Kent Keirsey, founder of Invoke.ai, framed this perfectly when he told me his philosophy:

“I want to earn every dollar that we make... as we earn the price increase over time, as we demonstrate the value... that is how we increase our prices.”

That’s what this chapter is about: building the evidence to earn your price, so you can broadcast that belief & confidence to the market.

Every founder eventually reaches the same moment Alex did.

They’ve proven value, won customers, but still feel awkward saying the number out loud.

That’s the sign you’re ready to do the real work: turning pricing from a source of anxiety into a source of conviction.

From Discovery to Design

Once you have this conviction, you’ve solved the first half of the problem.

You’ve used discovery to find the value.

The next step is to package that value.

This moves us from the “what” of WTP to the “how” of merchandising.

It’s time to take your newfound confidence in what your market will pay and build a GTM and packaging schema that captures it.

In the next chapter, we move from discovery to design. It’s time to talk about packaging.

Guest Perspective: Madhavan Ramanujam

“Price is more than just a dollar figure; it is an indication of what the customer wants — and how much they want it.

It is the single most critical factor in determining whether a product makes money.

Yet so often it is an afterthought, a last-minute consideration made after a product is developed.”

— Madhavan Ramanujam, Monetizing Innovation

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Thank you for reading.

As a reminder, to get your copy of You’re Leaving Money on the Table, click here (online) or click here (print).