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. A lot of it ends the same way. The spend runs for a quarter, the pipeline looks busy and closes nothing, and the leadership team decides the market was the problem.

The market was rarely the problem. It had money, and the size of that budget was the entire case for going in.

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 proves one thing: these companies can buy. It leaves open whether they will, and whether you are the fiftieth version of a pitch they have already learned to hang up on.

This is my opinion, and I have earned it the expensive way. The “they have money” case leaves out a few things.

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 ready to change. Usually it isn’t. Budget and appetite for change have almost nothing to do with each other, and confusing them is the most reliable way to turn a promising segment into a graveyard.

Some of the largest, best-funded organisations I have seen run their core on spreadsheets, and not as a stopgap - as the actual system of record. No automation, no dashboard anyone trusts, just a workbook on a shared drive and one person who knows where everything is and dreads the day they leave.

None of that is 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, and they don’t, because the people who would have to use the new thing do not want to change how they work, and no budget line overrides that.

Adoption comes down to mindset, and no purchase order buys it. A company can buy your software and never touch it, which is worse than a lost deal: it churns without a word 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 adopted is a 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 hardened them. 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 probably the fiftieth rep through the door, and the forty-nine before you salted the earth.

A tight cluster looks great when you are sketching territory on a map. Up close, it usually means a group of companies that have all built the same immune response, 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, and it doesn’t. 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, but the pattern underneath it. The past deals where the same problem showed up and the same approach solved it, two or three times over, are the repeatability that counts as evidence. That is what separates “this segment reminds us of a good one” from “we have closed this exact shape of problem before, and we know how we did it and what it took.”

To borrow from Bob Ross, none of this is a happy little accident. A happy accident is a deal you closed and cannot explain, worth nothing the moment you need to do it again on purpose. Repeatable evidence is the only kind worth betting a budget on, and it is the same reason a forecast built on hope keeps missing: hope is not a data source.

There is a catch underneath all of this. You can only find that pattern if the team uses the CRM, historically the 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 selling; the rest disappears into admin and the data entry they resent. So the system that holds the evidence for which game you can win is the same system the people with the evidence refuse to feed. No logged activity, no pattern - and without the 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 what turns a very confident guess into an actual strategy.

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

A guess with conviction does not stay small, which is where it starts to get expensive. 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 hoping people who have never heard of you will fill - and, somehow, leave ready to sign.

You ran ads for the event. Warming the market first was the step nobody took - no months of content that landed with these people, no reason for anyone in that segment to care about your name before the invitation showed up in an inbox they already associate with being sold to. So you pay premium rates to put a cold, over-pitched audience in a room, and then you read the empty seats as a market problem when the real problem was sequencing. A campaign you cannot tie to pipeline is a donation with a nice venue.

Strip away the venue and it is spray and pray with catering.

The money was never the question

None of this is an argument against spending. Done right, pay to play works. You spend to compete for a segment your own evidence points to, in a market you warmed for months before you ever asked for the meeting, and at that point the spend is amplifying something that already works.

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

The segment had money. It always does, and that was never the question.

The question was whether you had a game and whether you could prove it, and most of the time nobody bothered to check.