Closing the Enterprise Deal When You are Selling Change

In my last post, I discussed how to sell change to an organization—covering the discovery process, how to set up the deal to highlight latent pain, and ultimately how to get the prospect to embrace change. If you missed it, you can read the full article here: Why Selling Change in Technology is Key to Closing Deals.

However, even after you’ve successfully sold the idea of change, you often need to prove that the solution actually works. This is where most salespeople falter.

The Common Mistake in the Digital Age

Salespeople who have grown up in the Digital Age often make a critical mistake: they prioritize being customer-service oriented and do exactly what the prospect asks. When it comes to evaluating technology that creates change, this is one of the worst things you can do. Why? Because the prospect has no real frame of reference for how to evaluate your solution.

Think about it:

• They don’t currently work in the way your solution enables.
• They likely don’t have the right people in place to execute with your new technology.
• They don’t have the processes needed to implement and scale it.
• They have no peers or colleagues who have experience with your technology, especially if it's new to the market.

How could they possibly know how to assess it properly? So, why let them dictate how the Proof of Concept (POC) should be evaluated? If you do, you're setting yourself up for failure.

The Key to Selling Change: Guiding the Prospect

A key indicator that you’ve effectively sold the change, as I described in the previous post, is whether the prospect will accept your guidance during the POC phase.

Your champion should be supportive of your approach and actively sell it internally, while senior leadership and managers will back it because they want the POC to succeed. If the prospect reverts to their usual evaluation process, it’s a sign that you have more selling to do.

The Purpose of the POC

When the POC is set up correctly, it demonstrates that your product can solve the problems you’ve identified. It’s not about training them on how to use the product—because, ultimately, they’ll try it on their own. Initially, they might have some success, but they’ll inevitably hit roadblocks. When that happens, you step in to show them how easy it really is.

And then, here’s the key: you end the POC. Why? Because the goal of the POC isn’t to train them or implement the solution for them—it’s to prove that your solution can deliver on the promises you made.

POC vs. Pilot

Prospects often push for training during the POC phase, wanting to mitigate operational risk. They’re looking to not only prove that the technology works but also to figure out how to operationalize it within their organization. But that’s not the purpose of a POC, and it can be costly—essentially, you're implementing a pilot project before they’ve made a decision.

A POC is typically low-cost and designed to illustrate the potential of your solution. A pilot, on the other hand, is an actual operational trial, and it’s much more expensive. If you’re asked to run a pilot, make sure you're compensated for the resources and effort involved.

The Price Question

Another challenge you’ll face is the prospect trying to lock you into a price before you've fully established the value of your solution. My approach is straightforward: I’ll set a price if they commit to buying at the end of the POC. However, I also make it clear that if they don’t buy, the price will increase because the cost of sale rises as their perceived risk decreases.

Two Stories to Illustrate the Point

1. The $600K Deal that Turned into $1.2M In this case, after the initial discovery, the decision-maker asked, "How much is it?" My response was, “It depends on what you want me to do to prove the technology.” He replied, "Nothing, I’ll get you a PO by Friday." I said, "Okay, $600K—if I get the PO this week."

The next day, he called back saying they needed a POC. I agreed, but the price was no longer $600K. He asked, “How much is it now?” I told him, "I don’t know yet. We still have work to do." Over the next 60 days, we proved the technology. The result? The solution was worth about $3M per year to them. Two weeks later, they bought the technology for $1.2M.

1. The Startup’s $1M Pilot We were a startup, and our competition had given a prospect our name, assuming it would be easy to eliminate us. The prospect reached out and asked for a price. My response was simple: “We can’t give you a price until we understand your problem better.” The client gave a cursory overview of the problem, but when he asked for the price again, we still didn’t know enough.

After 45 minutes of him drawing the problem on a whiteboard, I asked, “How much do you think it’s going to cost you to solve this problem, TCO-wise?” He replied, “$20M.”

I then asked, “Do you even know if we—or any of our competitors—can solve this problem?” He admitted, “No, that’s exactly what I want to find out.” I said, “Would you be willing to spend 5% of that $20M to find out?” He immediately agreed. Two weeks later, we signed a $1M pilot, and later that year, they spent another $1M with us.

Before this, our company had never sold a solution for more than $250K.

The Moral of the Story

The key takeaway is that as a salesperson, you need to think like the prospect. You must understand how organizations evaluate risk and reward, and be prescriptive in guiding them. The “puppy dog” approach—doing whatever the prospect asks—will only set you up for failure when you're selling change to the enterprise.