Fit vs. Readiness: A Worked Example

This is one operator's experience. Use it as a reference for what the analysis looks like, not as universal rules.

The situation

A SaaS company had a defined ICP based on industry, company size, and tech stack. Pipeline was over 100% of quota. But sales cycles were lengthening, win rates were flat, and the sales team was working harder for the same results. The VP of Sales said they needed "more at-bats."

What the win/loss/no-decision comparison revealed

When we compared a full year of opportunities against the ICP, the written ICP did not align with all the customers who were buying.

The opportunities that became customers did not just fit the ICP. Something was happening inside those companies that gave them a reason to change: urgency around the problem, dissatisfaction with the status quo, or multiple stakeholders aligned around solving it.

Other companies fit the ICP too. They engaged, took meetings, asked good questions, but ultimately did nothing. The status quo was tolerable. They had no forcing function, no internal champion pushing for change, and no event that made inaction feel riskier than action.

The questions that changed the outcome

We stopped treating fit as the final answer and started asking:

• Was there a motivating trigger?
• Was the problem creating enough friction to force action?
• Had they already tried something that wasn't working?
• Was there a reason to make a change now instead of six months from now?
• What had disrupted the status quo enough to make change feel necessary?

The result

Over the next two quarters, average deal size increased from roughly $60,000 to $80,000. Win rates improved. Revenue grew 20%. Same product, same sales team. They got more selective about where they spent their time.

One signal increased buying probability by 400%

In another case, an enterprise SaaS company selling product management software found that when the CEO publicly used the word "innovation" across annual reports, investor calls, and interviews, those companies had a 400% higher probability of buying.

It did not mean they were shopping for product management software. It meant innovation had become a CEO-level priority, which suggested the status quo around product development was under pressure. That gave the team a reason to investigate what was changing inside the company.

The signal was specific to that company's motion. Your highest-value signals will be different. The method for finding them is the same: compare wins against no-decisions and identify what was observable before the deal started.