Selling Enterprise Software? Choose Pilot Programs for the Win

EDITOR’S NOTE: Because enterprise learning involves multiple disciplines and perspectives, we often invite experts from other organizations to share their insights. Today, Josh Squires, SVP of Strategy and Growth at Bongo, explains how to run pilot programs that drive B2B sales.

The Power of Strong Pilot Programs

Selling enterprise software is brutal. Even if your technology is flawless, you can still lose an opportunity. Why? It comes down to how artfully you manage the enterprise buying motion — including pilot programs.

Deals are rarely killed because of a solution’s quality. More often, it’s because the business case can’t survive all the rooms you’re not in, the budget reviews you can’t influence, the moments when people are asking “are we sure this is worth it?”, and the quiet conversations between people who have the final say on spend.

That’s why pilot programs can make or break you.

I’ve been on both sides of enterprise buying decisions. I’ve seen promising pilot programs with enthusiastic users die on the vine because the champion didn’t have enough proof to defend the investment. I’ve also seen modest, tightly scoped pilots turn into massive expansions because they made the champion look like a person who can deliver a safe, high-return win that aligns with leadership priorities.

So, how can you land on the right side of these decisions? It takes more than just knowing how to coordinate pilot programs. It’s about understanding what drives the broader enterprise buying motion — a complex, multi-step process organizations use to evaluate, test, and implement large-scale solutions.

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Where Do Pilot Programs Fit Into the Enterprise Buying Motion?

Unlike consumer purchases, enterprise deals involve numerous stakeholders, strict validation requirements, and significant organizational change. Every step in the enterprise buying motion is about demonstrating business value to the right people at the right time.

The difference usually isn’t about a product’s feature list. It’s about how you run the buying motion. And as the first step in the process, pilot programs play an integral role. But they are only one stage in a much broader arc.

Here’s the ideal sequence: Pilot. Validate. Then Launch. Let’s look at each phase…

Phase 1: Pilot Programs

Many people think of pilot programs as a trial run. Actually, it’s your first closing argument. And for your champion, it’s the audition for being the person who “found the win.”

So, it’s a mistake to think of pilot programs as a box-ticking exercise. Rather, treat them as a disciplined process that proves strategic value, reduces perceived risk, and positions the program champion as a hero who brought the right solution to the table.

Most pilot programs set out to answer this question: “Does the solution work?” But that’s the wrong question. If the financial decision-maker has signed off on a pilot, they already believe it works.

Instead, let this question guide you: “Will this solution move a key business metric in the right direction quickly enough to make investing in it at scale a no-brainer?”

What Makes Pilot Programs Fly? The Right Metrics

Effective pilot programs revolve around high-priority leadership-level metrics like market share, margin protection, risk reduction, and time-to-revenue. Scope them tightly to avoid noise in the results. This gives the champion 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 pilot programs 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 specified timeframe.
• Or they hand the champion a story that is too muddy to repeat upstairs.

My rule of thumb? If your pilot programs can’t make an internal champion look like the smartest person in the next leadership meeting, that trial is not ready to roll.

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Phase 2: Validation

Validation is when solutions tested in pilot programs prove their worth. That’s when “it works” becomes “we can’t afford not to scale this solution.” When validation is done well, your champion starts looking like someone who found the smartest investment in the portfolio.

By now, the tech has been proven. So, when you move beyond pilot programs, the focus shifts. Buyers need to determine if it’s smart and safe to put serious money behind the tech. Validation equips your champion to make a convincing argument in front of people who hold the purse strings. This means the business case must be strong enough to survive, even when you’re not present.

What Does Validation Look Like?

Let’s illustrate this concept. An 18% faster ramp is a metric. And $2.3 million in earlier revenue capture is a decision driver.

You’ll want to work with your champion to be sure questions leaders care about most are framed in their language: How quickly will this pay back? Will deployment disrupt critical business processes? Will we look smart for backing this option?

Your mission is to help the buyer feel safe by providing clean data, external benchmarks, and projections that take the edge off of perceived risk. This makes all the difference.

I’ve seen the impact of this firsthand. For one client, we cut customer onboarding time by four days. On its own, that’s interesting, but not game-changing. That’s why we connected it to accelerated ARR recognition, improved cash flow, and a direct hit on the CFO’s capital efficiency targets. The champion delivered the deck directly, and the decision-maker opened the meeting with, “If this plays out, it’s the best investment we’ve made this quarter.”

Validation tends to fail when teams use functional jargon, avoid total cost of ownership until procurement drags it out, or leave the champion without a clear, defensible scaling story. The test I use? If your champion can’t sell it without you, you don’t have a business case, you have a dependency.

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Phase 3: Launch

This is the moment of truth. It’s when you claim the win, or watch it start to unravel.

Going live isn’t the finish line. It’s the point where the investment must start paying visible, strategic dividends. Your champion needs fresh, demonstrable proof that they backed the right horse. This is when the champion’s reputation is solidified as a person who makes smart bets. Otherwise, they’ll be exposed to risk when priorities shift.

The Anatomy of a Launch

The best launches base rollout decisions on data that leaders can see and understand. They arm the champion with early wins, a first-month revenue lift, improved retention rates, and/or cost avoidance evidence they can use in leadership updates. This keeps the story current, adjusting to align with new priorities, while staying visible enough to keep the program from quietly turning into a budget line.

For one multinational rollout, we used capability scores from the pilot as a benchmark. 60 days later, those scores were up 24%, tied directly to revenue per rep. We condensed that data into one clear, visual slide for the champion’s leadership update. That single chart secured funding for an additional region before the quarter was over.

Launches tend to fail when teams treat go-live as the end, assume early enthusiasm guarantees adoption, or allow the original business case to get buried under competing initiatives.

My advice here is simple. If you keep providing fresh proof to your champion, they won’t lose their ability to defend the investment. This positions your solution for continued success.

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How to Navigate Pilot Programs and Beyond

No matter what you’re selling, a few constants hold true across industries, budgets, and deal size. Here are three universal rules:

1. Transparency is non-negotiable
Trust is the glue that holds the buying motion together. When you’re open and honest about both wins and misses, you build credibility and trust that compound over time. But the moment you start spinning the story to make things look better than they are, trust fades faster than you can recover it.

2. Speak in leadership language
No matter how innovative your product is, conversations about growth, margins, and risk will resonate with enterprise buying teams much more deeply than a list of cool features. Leaders are making investment decisions, not shopping for gadgets. So, tie your message to the business levers that matter most to them.

3. Lead with proof
Real, relevant data is golden. But wrapping it in a compelling human story beats even the most confident opinion, every time. Why? This gives decision-makers a vision of success, along with a measurable impact they can defend and real-world context that will remain top-of-mind.

The Enterprise Buying Motion Manifesto

If you sell enterprise software solutions, keep this in mind:

1. Pilot programs are not a test drive. They are your champion’s first shot at being a hero.
2. Validation is not about more data. It’s about making scale feel like the safest, smartest move in the portfolio.
3. The launch is not the end. It is a pivotal moment when you either lock in strategic value, or lose it to the next budget cut.
4. Even if your technology is flawless, you can still lose. What wins? The most compelling business case. And if you don’t build that case with your champion and financial decision-makers from day one, someone else will.

And if you’re on the purchasing side of the enterprise buying motion, always look for vendors who are willing and able to walk alongside you through every step in this journey. Choose a team that stays engaged and provides hands-on guidance, not just during pilot programs, but also through validation, launch, and beyond.

This kind of partnership ensures that solutions deliver measurable impact during every phase of the buying motion, while setting up buying organizations for long-term success.

NOTE: This article is adapted with permission from Bongo Learn. To find out more about how this video and AI platform helps organizations turn learning goals into reality, one successful business case at a time, visit Bongo online.

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