Footprint’s $35M Lesson: Why Political Risk Kills Enterprise Deals Faster Than Technical Risk

Footprint’s $35M Lesson: Why Political Risk Kills Enterprise Deals Faster Than Technical Risk

In a recent episode of Category Visionaries, Eli Wachs, CEO of Footprint, shared the moment he realized his startup was building something nobody would ever buy. The product worked perfectly. The forecasts were accurate. The technology was solid. And that’s exactly why it was going to fail.

The conversation happened with a retail VP who laid out the impossible position Eli was asking him to take: “I have a team of 50 people whose job it is to forecast what’s going to sell. If I use your product and it works, I have to fire 30 of them. And if I use your product and it doesn’t work, I still have to fire 30 of them because I just spent a bunch of money on software that doesn’t work.”

That single conversation crystallized a lesson most enterprise founders learn too late: political risk kills deals faster than technical risk ever will.

The Product That Worked Too Well

Footprint started as a merchandising analytics platform. The founding thesis made sense: retailers needed better ways to forecast which products would sell. The team built machine learning models that could predict product performance with real accuracy. “We were building a product that could tell merchandisers which products were going to sell well and which products weren’t,” Eli explains.

From a product perspective, everything checked out. The technology worked. Early pilots showed strong results. The ROI was demonstrable. But none of that mattered because the product had a fatal flaw that had nothing to do with features or performance.

Every successful implementation meant proving that an entire team of merchandisers was making suboptimal decisions. It meant telling a VP that the forecasting department he’d built and defended in budget meetings for years could be replaced by software. It meant asking someone to advocate for technology that made his own judgment look questionable.

This is political risk in its purest form: when your product’s success requires your buyer to admit they were wrong, restructure their organization, or put their own position at risk.

Why Technical Risk Gets All the Attention

Enterprise buyers are sophisticated about technical risk. They know how to evaluate whether software actually works. They run pilots. They check references. They bring in technical teams to assess architecture and security. Every procurement process has built-in mechanisms for de-risking technical decisions.

Political risk operates differently. It’s rarely discussed explicitly in sales cycles. It doesn’t show up in RFPs. You won’t find it in buyer personas or ideal customer profiles. But it’s often the real reason deals die in procurement, get stuck in endless evaluation cycles, or fail to renew despite strong technical performance.

The merchandising VP’s honesty gave Eli something most founders never get: a clear articulation of the political calculation his buyers were making. The math was simple and brutal. Adopting Footprint meant betting his career on being wrong about his own team. Success meant admitting he’d been overstaffed. Failure meant wasting budget on software that didn’t work. There was no scenario where the buyer came out looking good.

The Two Types of Enterprise Products

This conversation forced Eli to see enterprise software through a different lens. There are fundamentally two types of products: those that make buyers look smart and those that make them look questionable.

Products that make buyers look smart are typically framed as growth initiatives, innovation plays, or competitive advantages. They let buyers claim credit for forward-thinking leadership. A CMO who implements new marketing automation can talk about modernizing the stack and driving efficiency. A VP of Sales who adopts new forecasting tools can frame it as giving the team better weapons to hit targets.

Products that make buyers look questionable force them to explain what they were doing wrong before. They implicitly criticize past decisions. They raise questions about judgment and resource allocation. Even when the criticism is valid, asking someone to publicly validate it as part of a purchase decision is asking them to take on enormous career risk.

Footprint’s merchandising analytics fell squarely in the second category. The value proposition was essentially: “Your forecasting team isn’t very good. Use our software instead.” True or not, no VP was going to champion that message to their executive team.

The Pivot to Marketing

With six months of runway left, Footprint made a critical decision. They would keep the underlying technology—the data models, the forecasting algorithms, the analytics engine—but completely change who they sold to and how they framed the value.

“Marketers were where the budget was. They had budget, they had urgency, and they actually wanted to try new things,” Eli explains. This wasn’t just about finding buyers with budget. It was about finding buyers for whom adopting new technology was politically safe.

Marketing operates under different career incentives than operations. Marketers are expected to try new channels, test new tactics, and experiment with emerging technology. A retail marketer who implements marketing automation isn’t implicitly criticizing their own judgment—they’re showing they’re staying current with industry trends.

The same underlying product positioned as “help your team execute more campaigns faster” instead of “replace your team’s forecasting” changed everything about the political dynamics. Marketing managers could advocate for Footprint without putting their own positions at risk.

How to Diagnose Political Risk Early

Most founders don’t get the gift of a brutally honest VP laying out the political calculation. You have to diagnose it yourself by watching for specific signals in sales cycles.

The clearest indicator is when technical evaluations go well but deals stall in procurement. If your champion loves the product, pilots show strong results, and the ROI is clear, but the deal keeps getting delayed or stuck in “internal discussions,” you’re likely dealing with political risk.

Another signal is when buyers keep asking you to prove things you’ve already proven. If you’re in your third pilot, fourth ROI analysis, or fifth reference call, the buyer probably isn’t looking for more technical validation. They’re trying to build enough political cover to take the risk.

The most telling signal is in how champions talk about your product internally. If they’re framing it as an innovation play or competitive advantage, you’re probably in good shape. If they’re positioning it as fixing something that’s broken, you’re forcing them to take on political risk.

The Framework for Evaluating Political Risk

Before investing heavily in any market segment, map out the political dynamics of your buyer. Ask yourself: Does success with our product require the buyer to admit their current approach is wrong? Does it force them to restructure teams or eliminate headcount? Does it implicitly criticize their judgment or past decisions?

If the answer to any of these is yes, you need to either reposition the product or find different buyers. You can sometimes mitigate political risk through positioning—framing the product as an addition rather than a replacement, an enhancement rather than a fix. But fundamentally, you need buyers for whom adopting your product is politically safe.

Eli’s lesson from that Birmingham pub conversation was simple: “We were like, oh shit, we need to change what we’re doing.” The technology stayed the same. The target buyer changed everything.

Today, Footprint generates over $100M in ARR selling essentially the same underlying analytics and forecasting technology they built originally. The difference is they sell to buyers who can say yes without betting their careers on it.