Every enterprise AI pilot depends on two separate tracks to run smoothly for success. Both tracks require thoughtful planning and execution, but many companies fall short, and their AI pilots fail before they begin.
My team spent months on a proof of concept for a large insurer. This potential client created a bake-off scenario with high stakes: our document processing system, based on AI small language models, against their internal build and a leading frontier model. Their test would use their charts, images, handwritten notes, etc. and be scored on their terms. We won, and not by a little.
The deal died anyway. Not on our side of the table, but on theirs. What happened? They didn't have a funded business case, an approved timeline, or a budget line waiting on the other side of the demo. Our champion was sharp and genuinely bought in, but he didn't directly own the business line, and without that he had neither the budget nor the political capital to carry the work across the organization. When the business case finally went up the chain, it didn't get the backing it needed, and it missed. Months of their work and ours evaporated.
It was frustrating for everyone, and it was entirely avoidable.
In the months and years since, I've run dozens of these demos, mostly in insurance for claims, underwriting, and submission intake. The most crucial advice I have for every executive greenlighting an AI project is to understand that every pilot runs on two separate tracks, and they have almost nothing to do with one another.
Track one is technical. Can it work? How accurate is it? Does it fit the architecture, clear the security review, connect to the systems you already run? This is the track everyone obsesses over. It's where vendors compete, where the POC is scored, where the demo lives.
Track two is the business. Is there a funded case? An owner with authority? An approval path, a realistic timeline, a budget that's still there when next year's planning cycle hits? Who actually signs, and can they? This is the track that decides whether anything ships, and it's the one almost nobody staffs.
Here's the trap: winning track one tells you almost nothing about track two. A dazzling demo feels like progress, so everyone relaxes, but the fact is you've only cleared half of the problem that was never really in doubt. We won track one decisively for that insurer, and the pilot still died because no one was running track two with the same seriousness.
The uncomfortable part about my side of the table? Vendors are paid to win track one. The entire machinery of a POC, mine included, is engineered to produce an impressive technical result. Almost none of it is built to produce a funded production plan, because that's the customer's job, and unless a leader explicitly hands it to someone it doesn't belong to anybody. The result is two parties pouring themselves into the demo and neither one carrying the business case. The pilot succeeds. The initiative stalls. The post-mortem blames "the technology," which is usually the one thing that actually worked.
Sometimes the roadblock appears after you've "won" the client. A partner of ours sailed through the evaluation and moved into real use, and then they hit the roadblock. The rate limit on their plan was well below what production needed to run their document count. The technology worked, but they were missing a throughput plan. They neglected the commercial terms of their project; they didn't have a who-pays-for-scale conversation, also known as track two. It was never started because the "win" made everyone on their team feel as if the project was finished.
So what do success stories look like? Here's what's humbling as a technologist: my production successes run on the same technology as my graveyard. They use the same models with the same accuracy. The deciding factor isn't track one.
One of my most successful clients is a high-volume document operation that is running in production against a real backlog. From day one their leadership ran track two out loud. There was a clear, identified pain point and a commitment to the project with a budget to fix it. There was a named owner who could say "yes, integrate it," and mean it. The success criteria were concrete. And when we later hit a genuine platform limit, they escalated it into a road map conversation instead of using it as an exit. Their success can be traced to their strong leadership.
So, if you're about to greenlight an AI pilot it's critical to understand that track two will decide whether your project succeeds or fails before you hit the finish line.
You need to ask, and answer, specific questions before you begin. Who owns this project in production? Name an actual person who will hold accountability because the moment responsibility is spread out among a committee your project will stall. Who can be the executive to say yes and sign the check? It needs to be someone with the political standing in your company to see it through, rather than the person most enthusiastic about the project.
What's the funded path and timeline to scale if the project works? This needs to be decided before the kickoff because "if it works" is exactly when these projects tend to die.
Go ahead and run track one to prove it's possible. But you also need to fund, staff, and lead track two from day one. It is a mistake to hand over the entire project to an employee who is enthusiastic but doesn't own the line of business, no matter how much they believe in it.
The technology will do its job. The real question is whether anyone built the plan to see the project through.
