Go-to-market strategy and pricing are more connected than most founders realize — and leaving commercial questions until late in the build is one of the most common and costly mistakes in the startup journey. In this episode, I’m joined by Adrijana Daragon, founder of GTM Advantage, who works with technical founders to bring commercial thinking into the process earlier, before pricing becomes a guessing game anchored to competitors instead of value.

We get into the practical and structural side of what goes wrong — and what changes when founders start asking the right questions earlier.

In this episode:

• Why “too expensive” and “not right now” are rarely the signals founders think they are
• How discounting to close a deal quietly erodes trust with the very client you’re trying to win
• What a clear GTM strategy actually looks like — and the tell-tale signs it isn’t there yet

Press play and take a listen.

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A QUICK NOTE: If this is showing up in your business right now, it’s often a sign that pricing needs structure — not another tweak. Here’s how I work with clients to give them clarity.

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Episode Summary

There’s a pattern that shows up repeatedly in founder-led tech companies. The product gets years of focused attention. The technology is refined, the features are built, and the team grows around delivery. And then, at some point, the commercial question arrives — often later than it should. What do we charge? How do we go to market? Who’s actually buying this?

Adrijana Daragon, founder of GTM Advantage, has spent her career working with exactly these companies. Her observation is direct: the founders who struggle most with pricing are usually the ones who treated it as a downstream decision. Something to figure out once the product was ready. The problem is that by the time they get there, the commercial structure is already being shaped by habit and reaction — not by intention.

Why external benchmarks only take you so far

When founders do start thinking about pricing, the first instinct is usually to look outward. What are competitors charging? What does the market expect? Those questions aren’t useless, but they tell you what others have decided — not what’s right for your offer, your customer and the value you deliver.

Adrijana describes her own journey with this when she moved from selling on behalf of companies to pricing her own fractional CMO services. The emotional weight of pricing something that’s closely tied to your identity is different. Benchmarks gave her a starting point, but the real anchor only came later — once she had enough client experience to understand what her work actually produced. The number stopped being external and started being grounded.

That progression — from external reference to internal clarity — is not a shortcut. It requires doing the work of understanding your customers well enough to articulate the value before they ask.

Go-to-market strategy and pricing are interconnected

The episode highlights a point that often gets missed: go-to-market strategy and pricing aren’t independent decisions. They’re deeply interconnected, with each shaping the effectiveness of the other.

GTM covers how you show up in the market, how customers find you, how deals get made, and how delivery is experienced. Pricing sits at the center of all of it — because it signals value, shapes expectations and affects whether the right customers say yes. When the two are out of alignment, no amount of sales effort or discounting fixes the underlying problem.

Adrijana’s marker for a GTM strategy that isn’t working is simple: can the leadership team say with confidence where the next significant chunk of revenue is coming from, and do they have a repeatable system to get it? If not, the GTM work isn’t done — and the pricing probably isn’t either.

What “too expensive” usually means

One of the more useful reframes in this conversation is around how to interpret pricing objections. When a prospect says the price is too high, or that the timing isn’t right, the natural response is to look at the price. Lower it, soften it, add something in to sweeten the deal.

But that’s usually the wrong move. The objection is more often a signal about priority, fit, or urgency — not about the number itself. The prospect might be interested. They might even be the right client. But they’re not yet at the stage where this is the most important thing on their list. Discounting to push through that resistance doesn’t resolve the misalignment. It papers over it — and creates a different problem.

When you lower your price in response to hesitation, you signal that the original price wasn’t really defensible. That lands differently than you might expect. Instead of building trust, it quietly raises a question: if they dropped it that easily, was it ever worth what they said?

The trust dimension founders tend to underestimate

Adrijana is direct on this point: discounting to hit short-term sales targets damages trust. Not dramatically, not immediately — but over time, it shapes how clients perceive the business and the value of what’s being offered.

Trust in a B2B context is built through credibility, consistency, and demonstrated results. It takes time to establish and can be eroded faster than it was built. Price is part of that signal. A price that holds communicates that the business knows what it’s worth and can back it up. A price that moves under pressure communicates something else.

The deeper work — understanding who the real decision-makers are in a buying committee, what their actual objections are, and whether this is a real priority for them right now — is uncomfortable and takes time. But it’s what separates founders who are building durable client relationships from those who are constantly chasing the next deal.

What changes when commercial thinking comes earlier

The argument running through this conversation is not that pricing is the first thing founders should think about. It’s that commercial questions — who is this for, what do they actually need, what does success look like for them, and what is that worth — should be part of the product conversation from the beginning.

When those questions are asked early, they shape the technology in useful ways. They create early traction. They give pricing a grounded starting point instead of a guessing game. And they make the sales conversation easier because the founder already knows how to speak to the customer’s reality — not just the product’s capabilities.

Adrijana describes the kind of company that starts to grow with real momentum as one where the team can explain the customer’s problems and the value of their solution in plain language — so clearly that the customer says, “you really get this.” Getting there requires listening. It requires the discipline to stay close to the market and bring what you hear back into how the product and the offer are shaped.

The full conversation is in the episode. It’s worth the listen if you’re working through any part of this.

Favorite quotes from this episode

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Episode Links:

• Get access to the Pricing Toolkit
• Ever wonder Why Pricing Feels So Hard? Check out this page.

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Episode FAQ

1) What is go-to-market strategy and why does it matter for pricing?
Go-to-market strategy covers how a business shows up in the market, attracts customers, and delivers on its promise. Pricing is embedded in that — it signals value, shapes who says yes, and affects whether the business is building the right relationships. When GTM and pricing aren’t developed together, the gaps tend to show up in stalled deals and pricing that doesn’t hold under pressure.

2) When should a startup start thinking seriously about pricing?
Earlier than most do. Many technical founders treat pricing as a downstream decision — something to sort out once the product is ready. But the conversations that shape pricing well happen during the customer discovery process, not after. The earlier a founder understands what their customer values and what they’re trying to achieve, the more grounded the pricing will be.

3) What does it mean when a prospect says the price is too expensive?
It’s rarely just about the number. More often it signals a misalignment in timing, priority, or fit. The prospect may be interested, but this might not be their most urgent problem right now, or the decision involves stakeholders who haven’t been part of the conversation. Discounting in response to this objection usually doesn’t resolve the real issue — it just changes the number.