How Easy Is It to Buy From You?

How easy is it to buy something from your company? It sounds like a question about Sales, but the longer I have worked around complex enterprise deals, the less convinced I am that Sales is where the answer sits. From the customer's side, the proposition can look relatively straightforward: there is a problem, an outcome they want, something we believe can help and eventually a conversation about what it will cost. Behind the salesperson, however, sits an organisation trying to reconcile a much larger set of considerations. Finance is thinking about margin, cash flow, conversion, financial sustainability and risk. Operations is asking whether the business can actually deliver what has been financially modelled, at the cost and scale assumed. Legal has its concerns, implementation needs a credible timeline, technology may introduce dependencies, and somebody will eventually have to live with all the assumptions that made the business case work.

None of those perspectives is unreasonable. In fact, most of the controls surrounding a complex sale exist because somebody learned the hard way what happens when they are absent. A salesperson who can promise anything they like is dangerous, just as an organisation that refuses to take any commercial risk can make itself almost impossible to buy from. What interests me is the cumulative effect of all those individually sensible decisions, because the customer does not experience Finance, Operations, Legal and Sales separately. They experience one company, usually through a salesperson who is trying to make the whole thing coherent enough to buy.

Anyone who has sold complex enterprise solutions will recognise that there are often two negotiations happening at once. One is with the customer, where the seller is trying to understand what the organisation wants to achieve, align stakeholders, establish value and get to a decision. The other happens internally, where that same seller may be negotiating margin with Finance, feasibility with Operations, scope with Product, terms with Legal and implementation assumptions with people who may not meet the customer until months later. Some tension is healthy because the alternative is bad business, but there comes a point where the seller spends so much effort reconciling the organisation behind the offer that selling to the customer almost becomes the simpler part. That is where I start wondering whether we are still looking at a sales problem, or whether the organisation has pushed too much unresolved complexity towards the person standing in front of the customer.

What exactly have we won?

The ambiguity becomes even more interesting at signature. Closed Won has enormous psychological significance in a sales organisation: the contract is signed, the forecast converts, the booking appears and everyone quite reasonably celebrates. In a complex services deal, though, the company may still be six months or more from implementation and then face another period of commercial ramp-up before volumes, productivity, revenue and margin resemble the assumptions on which the deal was approved. During that time the organisation is spending money, allocating people and carrying delivery risk while waiting to discover whether the economics behave as expected. I have come to recognise this period as the zone of anxiety, because the customer has bought and Sales has sold, but the commercial outcome has not yet properly settled.

The understandable response is to make Sales care about what happens next, and I have experienced commission structures designed to do exactly that. Part of the commission was linked to closure, with a later true-up once implementation had progressed and the commercial reality became clearer. I understand the logic: the business wants quality of revenue rather than signatures at any cost, and nobody wants to pay a large commission on a deal that eventually turns out to be economically poor. The problem is that control over the outcome begins moving away from the salesperson almost immediately after the contract is signed. Implementation might slip, the customer may not reach projected volumes, operational productivity may take longer than expected, hiring could become more expensive or technology could create delays. Some of that may trace back to assumptions made during the sale, but much of it increasingly depends on decisions and execution elsewhere.

That is where commission clawbacks become difficult. Sales should absolutely be accountable for the commitments, assumptions and commercial concessions it helped create, but taking money back months later because the economics have changed is a different proposition when the seller no longer controls the variables driving those economics. There is also an awkward practical wrinkle: what if the salesperson has already left the organisation by the time the true commercial position becomes visible? The deal has not changed, but the organisation's ability to impose the consequence may have changed considerably. It makes me wonder whether compensation plans are sometimes being asked to solve an organisational accountability problem that should really be addressed elsewhere, because understanding the downstream economics of a deal is not the same thing as remaining personally responsible for everything that happens after it has been sold.

Completely removing the seller after signature creates another set of problems, however. Enterprise relationships are personal, and the seller may have spent a year or longer learning the politics of the customer's organisation, understanding why particular requirements matter and building trust with people who do not care how the supplier's internal RACI changes after the contract is signed. I have seen sellers remain deeply involved in implementation because they genuinely wanted to ensure that the customer received what had been promised, because the customer kept coming back to the person they trusted, or simply because they had a slightly control-freakish reluctance to hand over something they had spent months creating. If their commission was still exposed to what happened next, there was also a perfectly rational financial reason to stay close. The involvement often looked useful because problems were solved and context was preserved, but the cost sat somewhere less visible: the next prospect was not being developed, the next executive relationship was not being built and the next opportunity was not entering the pipeline.

This is where the line between pure business development and account management becomes much less theoretical. A business developer ultimately has to move on, whereas an account manager is expected to remain close, protect the relationship and find further opportunity. Large enterprise roles have a habit of blurring those definitions because a seller who wins a major customer often remains the person with the strongest commercial relationship and the best understanding of what might come next. There is nothing inherently wrong with that, but there is a point where success begins consuming the capacity required to repeat it. The question then becomes less about whether Sales should stay involved and more about what kind of involvement still creates value once day-to-day delivery belongs somewhere else.

That is one reason I became such an advocate of a good quarterly business review. I never saw much value in spending an hour reading last quarter's operational numbers back to people who could have read the slides themselves, although the performance data obviously matters because it tells us what is working, what has changed and where reality has diverged from expectation. The useful part comes when the operator, customer stakeholder and commercial person use that evidence to look forward. Perhaps demand has moved, a recurring workaround is telling us something about the operating model, priorities have changed or something the customer originally bought no longer quite fits where the business is heading. At that point the conversation moves naturally back to ambition: what are you trying to achieve now, and has that changed since the last time we sat together?

That is also where white space becomes far more interesting than a cross-sell list. The operator can see what is happening inside the service, the customer can explain why it is happening, and the commercially curious person can ask what it means for the future. Sales therefore remains connected to the account without needing to sit in every implementation meeting or act as the customer's permanent escalation path. The QBR becomes a deliberate point at which operational reality and commercial possibility meet, rather than a mechanism for proving that last quarter's SLA was 97.3 per cent instead of 96.8. In the best cases, it becomes part of the customer's own planning process, which is quite different from simply reviewing the supplier's performance.

The answer changes as the company grows

Scale makes all of this harder because the model that works beautifully with a handful of customers can become impossible to sustain as the business grows. A mature organisation can afford Business Development, Account Executives, implementation specialists, Customer Success and Account Management, although every layer of specialisation introduces another handover at which context can disappear. A scale-up may be neither ready nor able to create that architecture, and I am not convinced it should try too early. When the customer base is still relatively small and the proposition itself is evolving, there is enormous value in keeping the people who sell close enough to delivery to understand where the promise met reality, where it failed and what customers genuinely value once they have bought.

That overlap works until it begins to consume the very capacity the business needs for its next stage of growth. One customer requires a little help after signature, the next requires more, another needs an escalation and the first now wants to discuss expansion. Before long, the person who was supposed to develop the market is spending a substantial part of the week servicing business the company has already won. There probably is no magic customer number at which Business Development should suddenly separate from Account Management, because two complex enterprise clients can absorb more attention than twenty straightforward ones. The more meaningful cutover point is probably when maintaining continuity begins materially reducing the organisation's ability to create new business, at which point what previously looked like valuable overlap has become a capacity constraint.

At one stage in my career we worked with a model we called two in a box, pairing a commercial person with an operational programme leader around the customer. I found it extremely effective because I was genuinely interested in the operation and much of the most interesting white space became visible through understanding what was happening inside the programme. The operator brought a reality check that Sales could never reproduce from the outside, while I could often hear something in an operational discussion and recognise a broader customer need behind it. The model did not work equally well for everyone, though. Some sellers regarded everything after signature as Operations' territory, while some programme leaders saw commercial involvement as interference, and putting those people next to one another on an organisation chart did not magically create collaboration.

Where it did work, neither person needed to abandon their primary accountability. The commercial person could remain interested in delivery without trying to run it, while the operator could participate in conversations about future opportunity without feeling that every commercial discussion compromised their operational role. That kind of relationship depends heavily on trust, personality and incentives, which is perhaps why it is much easier to design than to replicate. It does, however, illustrate something important about scaling: the answer does not always have to be a clean functional separation. Sometimes what is needed is enough clarity to know who owns what, combined with enough curiosity to prevent those boundaries becoming walls.

That may be the hardest part of becoming easier to buy from as an organisation grows. Smaller businesses can often compensate for gaps with capable people who simply cross boundaries, pick up the phone and sort things out, which can create an extraordinarily responsive customer experience. As the business becomes larger, relying on those individuals becomes increasingly fragile, so processes, roles and controls appear for perfectly good reasons. The danger is that in making the model more repeatable, the company removes some of the responsiveness and customer intimacy that helped it grow in the first place. There is no obvious moment when one model becomes wrong and the other right, but there is a point where leadership needs to recognise that the balance has shifted.

The customer sees almost none of this architecture. They do not particularly care whether the person in front of them is classified internally as Business Development, Account Management, Customer Success or Operations, nor are they interested in which function carries the financial anxiety between signature and break-even. What they experience is whether the organisation understands what they are trying to achieve, whether the promises made during the sale survive contact with delivery, and whether the relationship remains useful when their ambitions move on.

That is why I keep coming back to what initially sounds like such a simple question. Asking how easy it is to buy from us forces us to look beyond the capability of the salesperson and into the organisation standing behind them, including how it prices risk, transfers responsibility, protects selling capacity and keeps enough connection to the customer to understand what comes next. The answer may tell us considerably more about the maturity of the commercial operating model than another round of sales training ever could.

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