In most advisory relationships, only one side has money at risk, and it is the client’s. The firm gets paid on the calendar; the outcome is something the client lives with alone. This is not a scandal. It is how professional services have been priced for as long as there have been professional services, and for a great deal of work it is the honest arrangement. But it is worth saying plainly, because once it is named it is hard to ignore: the people advising you on the biggest technology bets of the decade usually have nothing of their own riding on whether those bets pay off.
We think there is a rarer arrangement worth talking about. Not for every engagement, and not for every client; for the right ones, we are willing to put our own fee on the table next to your outcome. The phrase we use internally is chips on the table, and we mean it the way a poker player would. Skin, not sentiment.
This piece is about what that arrangement is, why almost no firm in our category offers it, and the genuinely hard problem that sits underneath it. It is also an invitation, though a selective one.
The retainer earns its place
First, a defense of the model we are supposedly disrupting. The monthly retainer is not broken, and we are not here to bury it. For ongoing leadership, the retainer is the right structure precisely because the value is continuous and diffuse. You are buying judgment, availability, the senior voice in the room when a vendor overpromises or a board asks a question no one internally can answer. That kind of value does not resolve to a single number at the end of a quarter, and pretending it does would cheapen it. Most of what a fractional CIO does well lives here, and most of our own engagements are structured exactly this way, by design.
So when we talk about putting chips on the table, we are not replacing the retainer. We are describing a different arrangement available for a different kind of work.
The arrangement almost no one offers
Here is the part that tends to get a CEO’s attention. For engagements where the value is sharp and measurable, we will tie a portion of our fee to the result. If the number moves, we share in the upside. If it does not, we have given something up too. We co-design the target with you before any of it starts, and we both sign up to the same scoreboard.
It is worth being honest about how unusual this is. Performance-based pricing is common enough in functions where the result announces itself: the marketing advisor who takes a slice of attributed revenue, the finance advisor whose bonus rides on the raise, the procurement consultant paid out of the savings they find. In the fractional CIO category, it is close to nonexistent. The entire field is anchored on retainers, and the most outcome-minded firms go no further than talking about outcomes; very few will actually put their own compensation at risk against one.
We will, for the right engagement. That last clause is doing real work, and we will come back to it.
Why technology leadership has been the holdout
The obvious question is why. If shared-upside pricing works in marketing and finance and procurement, why has it skipped technology leadership almost entirely?
The answer is that technology value is famously diffuse, and that is not an accident of how firms bill; it is the nature of the work. A marketing campaign produces attributable revenue. A capital raise produces a number with a comma in it. The contribution of good technology leadership shows up everywhere and nowhere: in the breach that did not happen, the system that did not buckle under growth, the vendor contract that quietly stopped bleeding margin, the integration that let two teams stop doing the same work twice. Real value, and almost impossible to pin to one clean figure. So the category did the rational thing. It defaulted to retainers and stopped trying.
We think stopping there was a mistake, and that the difficulty is the opportunity.
The right metric is the key · and the challenge
This is the center of the whole thing, so we want to be direct about it. The willingness to share risk is not the rare ingredient. Any firm can announce it tomorrow. The rare ingredient is the ability to find the number.
The actual skill, the one that took us years to build and that we treat as core craft, is this: sitting inside a business where the value of technology is spread across a dozen places, and isolating the single figure our work most directly moves. Sometimes it is operational, such as administrative hours per producing employee, cost per transaction, or the time it takes to bring a new location or hire online. Sometimes it is financial, a specific line of spend or a specific source of leakage. It is almost never the obvious metric, and it is never the same twice. Constructing it is part diagnosis, part negotiation, and part judgment about which number is both meaningful to your business and clean enough that neither of us will argue about it ninety days from now.
That is the work we will not reduce to a template, because it cannot be one. It is also the reason the shared-upside arrangement is not a gimmick. Anyone can offer to share risk; very few can define the thing worth sharing it against. When we sit down to build that number with you, that is the part you are actually buying, and it is the part no competitor can copy by reading an article.
For the right engagement
Now the selective clause we flagged earlier. We do not offer this on every engagement, and we would be doing clients a disservice if we did. Shared-upside pricing only makes sense when a few things are true at once: the value is genuinely measurable, the lever is one we can meaningfully pull, and the person across the table has the authority to commit to a scoreboard and to act on what it says. When those conditions hold, the arrangement aligns us more tightly than any retainer can, because we win the way you win. When they do not, the honest answer is a clean retainer and no theater about it.
So this is an invitation, but a real one rather than a blanket one. If you are weighing a technology bet where the outcome matters enough to measure, and you would rather your advisor had something riding on it alongside you, that is exactly the conversation we want to have. We will tell you quickly and candidly whether your situation is one where chips belong on the table.
That willingness is the whole point. Most of the people advising you on this will never put anything of their own at stake. We will, when the engagement earns it. The question worth asking any advisor, including us, is simple: what do you have on the table, and what happens to it if you are wrong?
