Mastering The Enterprise Buying Motion

Josh Squires, SVP of Bongo, talks turning pilots into business cases that win.

Here’s the thing: in enterprise sales, the tech can be flawless, but you can still lose.

It’s rarely the software or the service that kills the deal. More often, it’s that the business case can’t survive the rooms you’re not in, the budget reviews, the “are we sure this is worth it?” moments, the quiet conversations between people who have the final say on spend.

I’ve been on both sides of this. I’ve watched promising pilots with enthusiastic users die on the vine because the champion didn’t have enough proof to defend the investment.

And I’ve seen modest, tightly scoped pilots turn into massive expansions because they made that champion look like the person who delivered a safe, high-return win that aligned perfectly with leadership’s priorities.

That’s the essence of the enterprise buying motion, the complex, multi-step process organizations use to evaluate, test, and implement large-scale solutions. Unlike consumer purchases, enterprise deals involve numerous stakeholders, strict validation requirements, and significant organizational change. Every step is about demonstrating business value to the right people at the right time.

The difference-maker isn’t the feature list, it’s how you run the motion. For me, that’s always been Pilot, Validate, then Launch, not as a box-ticking exercise, but as a discipline that proves strategic value, reduces perceived risk, and positions your champion as the hero who brought in the right solution.

Phase 1 – Pilot

A pilot isn’t a trial run. It’s your first closing argument… and your champion’s audition for being the person who “found the win.”

Most pilots set out to answer, “Does it work?” But if the financial decision-maker signed off to even get to a pilot, they already believe it works. The real question is, “Will this move a top business metric quickly enough to make scaling a no-brainer?”

The strongest pilots lock onto leadership-level metrics, things like market share, margin protection, risk reduction, or time-to-revenue and

then scope them so tightly there’s no noise in the results. That way the champion has a clean, defensible win they can present upstairs without you in the room. And every number is documented as if you’re writing their business case for them.

One example that sticks with me was a 45-day pilot for a global SaaS company. We zeroed in on a single high-margin product line and used asynchronous practice with AI scoring to measure partner capability before launch. The results projected a 15% faster time-to-revenue, which is exactly what leadership had called out as a quarterly priority. The champion took those numbers into a budget meeting and walked out with approval before the steering committee had even convened.

When pilots fail, it’s usually for one of three reasons. They measure “engagement” instead of outcomes that actually matter. They promise ROI that can’t be delivered in the timeframe. Or they hand the champion a story that’s too muddy to repeat upstairs. My rule of thumb? If your pilot can’t make your champion look like the smartest person in the next leadership meeting, it’s not ready.

The Rules That Never Change: Tips for Navigating the Enterprise-Buying Motion

Across industries, budgets, and deal sizes, I’ve found three constants that hold true no matter what you’re selling.

Transparency is non-negotiable. When you’re honest about both wins and misses, you build credibility that compounds over time. But the moment you start spinning the story to make things look better than they are, you erode trust faster than you can recover it. You have to speak in leadership’s language.

Conversations about growth, margin, and risk will resonate far more than a list of cool features, no matter how innovative your product is. Leaders are making investment decisions, not shopping for gadgets, so tie your message to the levers they care about most.

Always lead with proof. Data paired with a compelling human story will beat even the most confident opinion, because it gives decision-makers both the measurable impact they can defend and the real-world context that makes it stick in their minds.

The Buying Motion Manifesto

A pilot is not a test drive. It’s your champion’s first shot at being the hero. Validation is not about more data. It’s about making scale feel like the safest, smartest move in the portfolio. Launch is not the end. It’s when you either lock in strategic value or lose it to the next budget cut.

The tech can be flawless and still lose. The business case is what wins, and if you’re not building it with your champion and the financial decision-maker from day one, someone else is.

At Bongo Learn, we walk alongside every customer through this very journey. Our team provides hands-on guidance through the Pilot, Validation, and Launch stages, ensuring your implementation delivers measurable impact at every step. Learn how we can help turn your enterprise goals into reality, one successful business case at a time.

Josh Squires is SVP of Strategy and Growth at Bongo. Connect with him here: https://www.linkedin.com/in/joshsquires/