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Most enterprise buyers surface symptoms, not problems. A client reporting penalty costs isn't revealing the root issue—just downstream impact. Valentina uses the five whys methodology to drill into actual pain: "A client can tell me, hey, I'm paying X amount of dollars in penalties. That's not necessarily the root cause, it's just a symptom of the actual pain." This prevents building features that address surface-level complaints while missing the structural problem. The real issue might be data fragmentation across systems, lack of visibility into supplier performance, or decision-making bottlenecks—each requiring different solutions.
Nauta kills traditional POCs entirely because "it implies that they are testing us and that it's not a collaborative process." Instead, they offer contract exit clauses if expectations aren't met while requiring upfront commitment. This only works when you have proven results and can confidently deliver value. The insight: POCs create evaluator-vendor dynamics where the burden of proof sits entirely on you. Paid engagements with performance-based exits create partner dynamics where both parties invest in success. For early-stage companies without case studies, this won't work—but once you have repeatable results, test this approach.
Nauta starts every engagement with 3-4 cost reduction KPIs—penalties, reconciliation time, manual labor automation—then transitions to revenue generation through fill rate optimization and cash-on-cash improvements. "You need to go beyond just cutting costs. That way you transition from a nice to have to a must have." Supply chain has historically been viewed as a cost center; proving top-line impact changes budget conversations entirely. This matters because cost reduction has a ceiling (you can only cut so much), while revenue generation creates expanding budget headroom. Map your product capabilities to both from day one.
Novel UX creates adoption friction in risk-averse verticals. Valentina learned this after initially building more advanced interfaces: "The industry didn't need a Tesla, they needed the good old Chevy that they understood and they could trust." Nauta built tables that look exactly like Excel but with full automation underneath. Users see familiar row-column structures, formulas, and workflows—the backend does the heavy lifting. This is counterintuitive for product teams trained to innovate on UX, but incumbent interface patterns reduce change management overhead. Ask: what does your ICP already use 8 hours a day? Build that wrapper first.
Single-threaded discovery captures one perspective, which inevitably includes blind spots. Valentina emphasizes talking to different functional areas: "We all have limiting beliefs and so mapping for different areas of the organization is extremely important in order to actually build a product that solves the pain end to end." An operations manager might prioritize speed, the CFO wants cost visibility, and warehouse managers need accuracy. Each views the same workflow through different lenses. Multi-stakeholder discovery also reveals political dynamics—who actually drives purchasing, who will resist change, where implementation will stall.
How Nauta Refuses POCs and Layers Revenue Generation on Cost Reduction
Most AI companies get stuck running endless pilots. They demonstrate 20% efficiency gains, automate manual processes, and still never convert to production contracts. Valentina Jordan, CEO and co-founder of Nauta, built a different playbook: refuse POCs entirely, demand commitment upfront, and prove revenue generation—not just cost savings.
In a recent episode of BUILDERS, Valentina shared how Nauta evolved from Excel automation to building data infrastructure for mid-market shippers managing 600+ suppliers across 40+ countries—and why their contrarian go-to-market strategy works where conventional approaches fail.
The Excel Problem: Operators Ignore Six-Figure Tech Stacks
Valentina’s co-founder Rafa grew up in a family of distributors—one of the biggest food distributors in the Caribbean and South US, later acquired by Performance Food Group. He came to Valentina with three specific problems: systems fragmentation (ERP, TMS, WMS operating in silos), tribal knowledge locked in operators who’d worked there 20-30 years, and no single source of truth for decision-making.
The critical question: was this a family business anomaly or an industry-wide problem?
They ran discovery across Stockholm, Japan, Chile, Argentina, Colombia, Denmark, and the US. The pattern held everywhere. “Everyone of these companies, which are shippers, were all using Excel even though their company was paying hundreds of thousands of dollars on their tech stack,” Valentina explains.
This wasn’t about users preferring spreadsheets. “These people don’t choose to work in Excel because they like it. It’s just their only option that allows them to personalize, be extremely agile and be able to easily collaborate with their team,” Valentina notes. The expensive systems couldn’t adapt to the actual workflows, so operators built shadow processes in Excel.
That insight shaped Nauta’s first product decision: meet users in Excel, not in a new system requiring adoption.
Shipping Familiar Interfaces Over Novel UX
Product teams trained to innovate on user experience face a counterintuitive reality in conservative verticals: novel interfaces create adoption friction, regardless of functional superiority.
“One of the biggest challenges as a founder was understanding that the industry didn’t need a Tesla, they needed the good old Chevy that they understood and they could trust,” Valentina explains. Nauta built tables that look exactly like Excel—rows, columns, familiar formula patterns—with full automation running underneath.
This isn’t about compromising on capability. It’s about reducing change management overhead by wrapping sophisticated technology in incumbent interface patterns. Users see the workflows they already know; the backend handles the complexity.
The tactical question for founders: what does your ICP already use eight hours a day? Build that wrapper first, even if your product sensibility pushes toward something more ambitious.
Structuring POC Alternatives That Demand Mutual Investment
Nauta’s no-POC stance fundamentally reframes enterprise sales dynamics. Traditional POCs position you as a vendor being evaluated, with all execution risk sitting on your side while buyers passively observe results.
“We don’t do POCs and the reason why we don’t do POCs is because it implies that they are testing us and that it’s not a collaborative process,” Valentina states. “We can put clauses in the contract where if we definitely don’t meet expectations, we’re not going to tie you and you can’t leave. But we need your commitment.”
This only works when you have repeatable results and can confidently deliver value. The structure requires: performance-based exit clauses that protect the client, paid engagements from day one (not free pilots), and mutual commitment where both parties invest in success.
Early-stage companies without proven case studies can’t execute this. But once you have repeatable outcomes, test this approach—it eliminates the dynamic where buyers use POCs to indefinitely delay purchasing decisions.
Measuring ROI at the Economic Buyer Level, Not End Users
Success metrics must matter to whoever controls budget, not just operational users. Nauta learned this distinction early.
“A lot of the times the user won’t see the big picture of what actually is moving the needle for the company,” Valentina explains. Their buyers are CFOs, company owners, or maximum two levels down from ownership—not the warehouse managers or operations staff using the product daily.
This changes which metrics drive renewals and expansion. End users care about task completion speed or interface ease. Economic buyers care about margin impact, working capital efficiency, and revenue per employee.
Nauta tracks both layers: operational metrics that keep users engaged, and financial metrics that justify continued investment at the executive level.
The Five Whys: Distinguishing Symptoms From Structural Problems
Enterprise buyers surface symptoms, not root causes. Someone reporting penalty costs isn’t revealing the actual problem—just downstream financial impact.
“A client can tell me, hey, I’m paying X amount of dollars in penalties, right? That’s not necessarily the root cause, it’s just a symptom of the actual pain,” Valentina explains. “So being able to drill down into that five whys is super important in order to actually develop the product.”
The five whys methodology prevents building features that address surface complaints while missing structural issues. Penalties might stem from data fragmentation preventing proactive intervention, visibility gaps into supplier performance creating reactive rather than predictive operations, or decision-making bottlenecks where critical calls get escalated too slowly.
Each root cause requires different solutions. Without the five whys, you risk becoming what Valentina calls “a software factory just trying to solve for the pain instead of the symptom.”
Valentina also emphasizes multi-stakeholder discovery: “We all have limiting beliefs and so mapping for different areas of the organization is extremely important in order to actually build a product that solves the pain end to end.”
Operations wants speed, CFOs want cost visibility, warehouse managers need accuracy. Single-threaded discovery captures one perspective—and inevitable blind spots.
Transitioning From Cost Reduction to Revenue Generation
Cost reduction gets you in the door. Revenue generation makes you indispensable. Nauta structures every engagement to prove both.
“We’re firm believers that in order for AI companies to surpass that PoC stage, you need to generate additional revenue,” Valentina emphasizes. “You need to go beyond just cutting costs. That way you transition from a nice to have to a must have.”
Their framework: start with 3-4 cost reduction KPIs (penalties, reconciliation time, manual labor automation), then transition to revenue metrics like fill rate optimization (eliminating stockouts and overstock) and cash-on-cash cycle improvements.
This matters because cost reduction has a ceiling—you can only eliminate so much waste. Revenue generation creates expanding budget headroom and changes positioning from operational efficiency tool to strategic growth enabler.
Supply chain has historically been viewed as a cost center. Proving top-line impact changes that conversation entirely.
Moving Upmarket to Find Acute Pain
Nauta initially targeted smaller shippers, positioning as an AI teammate enabling revenue growth without headcount expansion. The market proved this insufficient.
“What we quickly realized was that was not going to be enough of a bleeding pain to actually transform the industry,” Valentina admits. “So we moved into this mid segment and these are companies selling between 200 million to a couple billion dollars in revenue.”
This segment faces enterprise complexity (600+ suppliers across 40+ countries on average) without enterprise resources or dedicated transformation teams. The pain is acute enough to drive purchasing decisions, and the contract values justify Nauta’s sales motion.
The lesson: nice-to-have pain doesn’t drive enterprise software adoption, regardless of ROI calculations. Find where the problem causes genuine operational or financial distress.
Market Timing: From Hiding AI to Leading With It
When Nauta launched January 7, 2025, Valentina and Rafa deliberately downplayed AI capabilities. “Rafa and I were actually not very direct with our clients that we’re an AI company. We were running 100% on AI internally, but weren’t showing them like with an agent, the automations that we’re doing for them because the industry wasn’t as receptive.”
Eight months later, at Manifest 2025 (7,000+ attendees, one of supply chain’s largest conferences), the market had shifted. “People are looking for solutions, they’re willing to listen, they understand that a change, that things are changing, either they like it or not.”
Three forces converged: the pandemic exposing supply chain as strategic rather than operational, generational workforce transition as 20-30 year operators retire with undocumented institutional knowledge, and executives gaining personal AI comfort through consumer applications.
The tactical insight: B2B buyers increasingly test enterprise tools in personal contexts first. This affects adoption timelines and reduces the education burden on vendors.
Geographic Focus Despite Global Opportunity
For 2026, Nauta made a counterintuitive decision: focus exclusively on the US despite operating in seven countries and receiving inbound from multiple geographies.
Valentina admits this was difficult given her background: “At Rappi we had an operation in nine countries and deciding to just focus one when we have inbound right from other countries, it’s rough.”
The rationale: “We are firm believers that with focus and very fast and sharp execution we will get to those countries. It’s just a matter of time.”
The US market alone represents sufficient opportunity (mid-market shippers doing $200M-$2B revenue), and geographic expansion creates execution complexity that slows core product development. Better to dominate one market than spread thin across many.
The Long Game: Building Data Pipes for Global Supply Chain
Nauta’s vision extends beyond Excel automation to infrastructure enabling seamless data flow between the 12-13 stakeholders touching every product in global supply chain.
“You can go to Norway, you can go to Brazil with your credit and debit card in the US and you can pay your coffee anywhere. And the merchant, they acquire, have the rails in place for everything to be able to connect, communicate. That doesn’t happen in supply chain,” Valentina explains.
Starting with shippers provides strategic positioning. “Shippers for us are the holy grail in the global supply chain. They own the product, they pay for everyone to do their job and help the movement. And the third and most important, they have access to the whole information.”
This wedge strategy—own the entity with product ownership, payment authority, and information access—creates the foundation for expanding to other supply chain stakeholders.
Nauta’s approach demonstrates that escaping pilot purgatory requires more than proving ROI. It demands the confidence to refuse POCs when you have proven results, the discipline to layer revenue generation on cost reduction, and the product wisdom to ship familiar interfaces even when your instinct pushes toward innovation.