Pay to play is only good if you know what your game is

A sales leader picks a niche. The reasoning is always the same, and it always sounds sharp in the room: this segment has money. They can afford us. Let’s go all in.

I have watched this decision get made more than once, by people more senior and more capable than a quick summary would suggest. And I have watched a lot of it end the same way - a quarter of spend, a pipeline that looks busy and closes nothing, and a leadership team quietly deciding the market was the problem.

The market was not the problem. The market had money. That was the entire case for going in, and it was never a case at all.

Pay to play - spending to enter a market and compete for its attention - is a real strategy. But it only pays if you already know what game you are playing, and you have the receipts to prove you can win it. Money in the segment tells you they can buy. It tells you nothing about whether they will, whether they are ready, or whether you are the fiftieth version of the same pitch they have already learned to hang up on.

This is my opinion, and I have earned it the expensive way. Here is what the “they have money” case leaves out.

Money buys nothing you can’t already run

The first thing hiding inside “they can afford us” is the assumption that a company with budget is a company ready to change. It is not. Budget and appetite for change are different things, and confusing them is the most reliable way to turn a promising segment into a graveyard.

Here is the part that still surprises people. Some of the largest, best-funded, most operationally heavy organisations I have seen run their core on spreadsheets. Not as a stopgap. As the actual system of record. No AI, no automation, no dashboard anyone trusts - a workbook, a shared drive, and one person who knows where everything is and is quietly terrified of the day they leave.

It is not a money problem. Surveys still put a large share of finance and operations teams on spreadsheets and little else. These are companies that could sign the cheque tomorrow. They don’t, because the people who would have to actually use the new thing do not want to change how they work - and no budget line overrides that.

Adoption is a mindset, not a purchase order. A company can buy your software and never adopt it, and that is worse than a lost deal: it is a won deal that quietly churns and then tells everyone in its network that you did not work. If the people who would use the tool were never going to change, the money in the account was always a mirage. Getting a system actually adopted is a different, harder job than getting it bought.

A cluster of prospects is a cluster of people already sick of the pitch

The second assumption is geography as destiny. There are forty companies in this one city, the thinking goes, all with the same profile - land a handful and the year is made.

Except a dense cluster of near-identical companies is the most heavily-worked list in the market. Every salesperson before you did exactly the same arithmetic. Those forty companies have not been sitting there waiting for you. They have sat through the pitch - your pitch, more or less - a dozen times already.

And that prior experience usually made them harder, not softer. Sales, done the way it is too often done, leaves a residue. Fewer than one in five buyers say they trust a salesperson at all, by HubSpot’s numbers. In a segment that has been pitched to exhaustion, you are not the first through the door. You may be the fiftieth, and the forty-nine before you salted the earth.

Density looks like opportunity on a map. On the ground it often means the whole cluster has already built the same immune response - and it is pointed at you before you open your mouth.

Without evidence, you are spraying and praying with a bigger budget

The third assumption is that instinct scales. It does not. In a saturated B2B-tech segment, cold outreach converts in the low single digits, and “we think this market is good” is not a number you can plan against.

So where is the evidence meant to come from? The same place it always does, and the same place nobody wants to look: your CRM. Not the pipeline report - the pattern underneath it. The past deals where the same problem showed up and the same approach solved it, twice, three times, five times. That repeatability is evidence. It is the difference between “this segment reminds us of a good one” and “we have closed this exact shape of problem before, here is how, here is who, here is what it took.”

That is evidence. It is not, to borrow from Bob Ross, a happy little accident. A happy accident is a deal you closed and cannot explain. Evidence is a deal you closed and can repeat on purpose - which is the only kind worth betting a budget on. It is the same reason a forecast built on hope keeps missing: hope is not a data source.

And here is the trap inside the trap. You can only mine that pattern if the team actually uses the CRM - historically the single most hated piece of software a sales rep will ever be handed. By Salesforce’s own State of Sales research, reps spend well under half their week actually selling; the rest disappears into admin, internal meetings and the data entry they resent. So the one system that holds the evidence for which game you can win is the one system the people with the evidence refuse to feed. No logged activity, no pattern - and no pattern, no strategy.

Poor data quality already costs organisations an average of 12.9 million dollars a year, on Gartner’s estimate, and a B2B database decays by roughly a fifth every twelve months. So even where the evidence exists, it rots the moment the team stops touching it. Evidence-based targeting is not a nice-to-have on top of the strategy. It is the difference between a strategy and a very confident guess.

Then you set the budget on fire, with a logo on it

Here is where the guess gets costly, because a guess with conviction does not stay small. Once leadership commits to the experiment, they hit the segment from every channel at once.

Digital ads, and then heavy remarketing to chase the people who ignored the first ad. PR in the local trade press. And the centrepiece: a glamorous event, in a nice venue, that you are quietly hoping people who have never heard of you will fill - and, somehow, leave ready to sign.

You ran ads for the event. What you did not do is warm the market. No months of content that actually resonated with these people. No reason for anyone in that segment to care about your name before the invitation landed in an inbox they already associate with being sold to. So you pay premium rates to put a cold, tired, over-pitched audience in a room, and then you read the empty seats as a market problem instead of a sequencing one. A campaign you cannot tie to pipeline is a donation with a nice venue.

That is not going to market. That is spray and pray with catering.

The money was never the question

None of this is an argument against spending. Pay to play, done right, is exactly right. You spend to compete in a game you have already proven you can win, against a segment your own evidence points to, in a market you warmed for months before you ever asked for the meeting. The spend amplifies something that already works.

Done wrong, it is a well-funded version of the thing junior reps get scolded for - spraying and praying, just with a bigger invoice and a better caterer.

The segment had money. It always does. That was never the question.

The question was whether you had a game, and whether you could prove it. Most of the time, nobody checked.