Consider two companies.
The first has strong product-market fit, brand recognition, inbound demand, good enablement, and customers already predisposed to buy.
The second is largely unknown, selling an unfamiliar product into a skeptical market where buyers need convincing that the problem matters.
In the first company, a mediocre or perhaps even bad salesperson may survive. Strong market conditions create momentum that can mask weak sales skills.
The second company offers nowhere to hide. Creating urgency, establishing credibility, overcoming uncertainty, and earning the right to move the buyer forward require the sharpest of sales skills just to stay afloat.
Product-market fit matters... as one factor in a much larger alignment calculus.
A company can have a good product, happy customers, strong retention, and real value in use while still making that product unnecessarily difficult to sell. Buyers may struggle to understand the company, encounter competitors first, or see the strongest customer proof only after the shortlist has formed. The product may deliver an obvious outcome after deployment while the company struggles to make that outcome believable before purchase.
Market alignment considers the degree to which what a company sells, how it expresses and proves that value, and how the market discovers, evaluates, believes, and buys its offering line up.
Product-market fit is one variable in an equation that also includes positioning, proof, discoverability, competitive differentiation, category clarity, buying friction, perceived risk, and customer evidence. Even the order in which the buyer encounters those things matters.
A product can fit the market while the company surrounding it remains badly misaligned with how the market buys.
Salespeople inherit the website and the category. They inherit the proof the company has made visible and the proof it has buried. They inherit the reputation, competitive position, buyer expectations, and friction created long before a prospect ever enters the pipeline.
Then we measure their performance as though they created the environment themselves.
Over 60+ assessments, the pattern is hard to ignore
Every Strategic Navigation Assessment tests market alignment from the outside in. While a couple have come fairly close, I have yet to find a company where what the company believes the market understands and what the market can see are fully aligned.
More telling, over half revealed severe disconnects between what the company expected the market to understand on its own and what the market was looking to hear.
I recently completed a Strategic Navigation Assessment for a SaaS media company. The assessment is designed to examine a company from the outside in, under the same conditions the market experiences it.
I had no executive interviews, internal data, CRM access, customer interviews, strategy presentations, or explanations of what the company intended the market to understand.
Instead, the assessment examined what the company said and could prove about itself, what its competitors said and proved, where buyers would encounter each of them, what evidence was available at those moments, and where claims and proof separated.
Then I presented the findings to a group that knew the company intimately.
As we moved through the assessment, the responses were variations of the same realization:
“So that is why...”
The unfortunate answer... “Yes, yes it is.”
The assessment could see the consequences without knowing the internal causes.
That experience reinforced something I have been thinking about for some time. Companies have far more information about themselves than outsiders do, but more information doesn't automatically produce a clearer view.
Inside the company, every decision has history. Every message has an explanation. Every category choice has a rationale. Everyone knows what was intended.
The market does not get the benefit of intention.
Buyers experience what they can find, understand, compare, verify, believe, and ultimately trust enough to buy. They rarely receive all the internal context behind it, and almost never in the neat sequence the company assumes.
That creates an important asymmetry.
The company experiences itself through everything it knows. The market experiences the company through everything it can see.
The market does not need to understand why a company is misaligned to experience the consequences of that misalignment. That is why the outside-in view is useful. Remove the company’s explanation, and it becomes much easier to see the conditions under which the market is being asked to make a decision.
Which brings us back to sales
When revenue underperforms, the instinct is understandable: “fix sales.”
Change leadership. Change process. Change methodology. Change territories. Change compensation. Hire better people. And maybe that needs to happen.
But if discovery should come before diagnosis, there is a question that should come first:
Has the company created an environment where a capable salesperson can sell effectively?
That question goes well beyond whether the product fits the market.
Can buyers understand the value? Can they find the company when the problem becomes important? Can they distinguish it from the alternatives? Does proof arrive before belief is required? Can they resolve the risks standing between interest and commitment? Does the buying experience reinforce the value or work against it?
When those conditions are broken, hiring a better salesperson may simply give the company a more expensive person to chew through the misalignment.
Before “fixing sales,” establish what sales inherited
Sales inherits whatever the market already believes about the company. It inherits whether the company can be found, whether its value can be understood, whether its claims can be proved, whether competitors are easier to trust, and how much uncertainty the buyer must overcome before saying yes.
Great selling can mitigate some of that misalignment. The question is how much of it should have to be “handled in the field”.
That is why I increasingly believe an outside-in assessment should precede the decision about what to fix.
Look at what the market receives before asking the company to explain itself. Pressure-test the diagnosis before accepting it. Determine whether the mandate is right before handing it to a CRO and spending the next two quarters executing against it.
Then put the outside view next to the inside view.
The differences are where things get interesting.
Sam’s original point was about what difficult selling conditions reveal about salespeople.
I think there is another question hiding inside it:
Before asking whether the salesperson is good enough, ask why the company made selling so damn hard in the first place.
Product-market fit is part of that answer.
Market alignment is the bigger question.