I started selling technology when the dominant network management paradigm was “phone the engineer and hope.” I have sold root cause analysis software, network configuration management platforms, post-quantum cryptography advisory services, and data consultancy. I ran a hospitality business from one property to 21 across seven countries, which turns out to be a masterclass in commercial fundamentals when the product is a bed and a breakfast and the margin is tight.
What I am going to write here is not a framework for how to sell technology. There are plenty of those. What I want to describe is the small number of things that have been consistently true across 30 years, multiple product categories, multiple geographies, and multiple market conditions.
Some of these observations are uncomfortable. I will write them anyway.
The budget holder and the technical sponsor are solving different problems
This is the first lesson and the one most frequently forgotten.
The technical sponsor — the CTO, the head of engineering, the IT director — is solving a technical problem. They want the best solution to the specific challenge they have been tasked with addressing. They evaluate on functionality, architecture, support, and total cost of ownership. Getting the technical sponsor’s approval is a necessary condition for a sale. It is not a sufficient one.
The budget holder is solving a different problem. They are responsible for capital allocation decisions that they can defend to a board, a CEO, or a shareholder. They evaluate on risk-adjusted return, vendor credibility, implementation risk, and the story they would tell if the investment underperforms. They are not choosing the best technical solution. They are choosing the best investment case.
These are genuinely different evaluations, and the materials that win the first do not automatically win the second. I spent years at RiverSoft and SMARTS before I fully understood this. The companies that figured it out — who had separate materials, separate conversations, and separate relationship management strategies for the technical sponsor and the budget holder — were the companies that closed enterprise deals at velocity.
The companies that treated both conversations as technical conversations wondered why deals stalled in the final approval stage, consistently, in a way that no amount of product improvement resolved.
The best product rarely wins on product quality alone
RiverSoft had the best root cause analysis product in the market for a period. I know this because we beat the competition repeatedly in technical evaluations. We also lost deals we should have won, to products that were demonstrably inferior on the technical criteria the evaluation had been using.
The loss analysis was consistent. The deals we lost were lost on: vendor credibility in the specific sector, implementation risk perception, pricing structure, and the relationship the competitor had built at the board level — not the engineering level — before the evaluation began.
This is not a counsel of despair. It is a diagnosis of where the commercial effort needs to go. If your product is winning technical evaluations and losing commercial approvals, the problem is not the product. The problem is the commercial narrative, the relationship architecture, and the positioning at the budget holder level.
The best product needs a commercial effort that is proportionate to its quality. A technically excellent product with an average commercial effort will consistently lose to a technically adequate product with a sophisticated commercial effort. This is consistently true across markets and product categories. It is not a market failure. It is market dynamics.
Analogies close deals
I have watched this happen too many times to dismiss it as anecdote.
A technical explanation that is perfect in its precision and correct in every detail fails to move the budget holder. The same information, delivered through an analogy drawn from the budget holder’s own experience, lands immediately and produces a decision.
The reason is cognitive, not commercial: the budget holder cannot evaluate technical claims directly. They do not have the expertise. They evaluate the credibility of the person making the claims and the plausibility of the explanation. An analogy that maps the technical concept onto something the budget holder already understands is not a simplification — it is a bridge. The bridge lets them evaluate the idea rather than just the person asserting it.
I spent years at causal analysis companies before I developed reliable analogies for the technical concepts we were selling. Once I had them, close rates improved. Not because the product changed, but because the budget holder’s ability to evaluate what we were proposing improved.
The analogies have to be built carefully. A bad analogy — one that implies something the product cannot deliver, or that oversimplifies in a way that creates false expectations — is worse than no analogy. But a good one, used consistently and acknowledged as a simplification, is among the most powerful tools in a commercial conversation.
The fastest way to lose a deal is to win the wrong argument
The temptation in technology sales, particularly deep tech sales, is to win the argument. To demonstrate, conclusively, that the product is technically superior, the methodology is correct, the competitor’s claims are misleading, and the evaluation criteria that excluded you are misguided.
This temptation should almost always be resisted.
Winning an argument is a social transaction with a winner and a loser. The person you have just demonstrated to be wrong is now in the position of acknowledging their mistake or defending their original position. Most people, in a commercial evaluation, choose the second option. The result: you have won the technical argument and lost the relationship.
The faster path is to reframe rather than rebut. If the evaluation criteria do not favour your product, ask the budget holder what problem they are ultimately trying to solve and whether the current evaluation criteria are the most direct path to solving it. If the competitor has made a misleading claim, do not challenge it directly — demonstrate your product’s actual capability in a way that makes the comparison visible without the confrontation.
I done goofed, several times in my career, by winning the argument and losing the deal. I learned each time. The lesson was consistent: in commercial relationships, being right is less valuable than being useful.
Relationships built before the evaluation are worth ten times the relationships built during it
I had a colleague at SMARTS — I will not name him — who spent an uncomfortable proportion of his calendar having conversations that had nothing to do with any active deal. He was building relationships with budget holders and board members in companies that were not currently evaluating anything.
His close rate on formal evaluations was twice the team average. The reason: he was not unknown when evaluations began. He was a known quantity whose competence and judgement the budget holder already had an opinion about. The competitor who arrived for the evaluation without that pre-existing relationship was starting from zero.
This principle is more powerful now than it was twenty years ago, because LinkedIn has made pre-evaluation relationship-building accessible at a scale that was not possible when it required golf and dinners. A budget holder who has read three of your posts on the commercial implications of the EU AI Act before your first meeting is a materially different conversation than a budget holder who has never heard of you.
The commercial implication: the most valuable time investment in the sales cycle is the time before the sales cycle begins. Content, community, network visibility — all of these are commercial investments that pay returns during evaluations that have not yet started.
The business I built that had nothing to do with technology confirmed all of this
When I built Mad Monkey Hostels — starting with one property in Phnom Penh, Cambodia, in 2011 and growing to 21 properties across seven countries — there was no technology product to sell. The product was a bed, a bar, and an experience.
Everything I had learned about selling technology transferred directly. The budget holder (in hospitality, the traveller making a booking decision) is solving a different problem from the technical evaluator (the person who researched “best party hostel in Phnom Penh”). The best product does not win on quality alone — the property with better marketing and more user-generated reviews can outperform the objectively better property. Relationships built before the evaluation (reviews, social proof, word of mouth) are worth more than any last-minute pitch.
And the fastest way to lose a customer in hospitality is to win the argument with them when something goes wrong. I learned this specifically and painfully. You do not win the argument. You solve the problem and restore the relationship.
The universality of commercial principles across product categories is the thing I find most interesting after 30 years. The tools are different. The principles are the same.
For deep tech and AI founders building commercial approaches that work for non-technical buyers and budget holders, Steven works on commercial strategy engagements. Contact Steven directly to discuss your situation.
