At Emissary, we’re firm believers in the value of pilots. Some revenue teams are wary of them, but we believe they build trust by giving clients a feel for what they’re investing in. 

Pilots allow the customer to see real value immediately, thus shortening the sales cycle and building a relationship based on trust. And if you’re honest and transparent during the sales process, you shouldn’t have anything to worry about once the pilot runs its course and its time to sign a bigger deal.

We’ve learned a few key strategies for successfully selling pilots, and we’re confident these will help you earn your next deal faster, easier, and with less hassle than going straight to the big sell.

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Keep it simple

Your prospects are busy people. They’ve got a million things to do, and they’re always rushing from meeting to meeting. They don’t have time for complicated messaging, and they won’t retain anything from a slide with 20 bullet points on it. It’s not because they don’t want to or aren’t interested—they’ve just got a lot of tasks to complete, and remembering a sales pitch isn’t at the top of their list. So I’ve learned to keep it as simple as humanly possible.

For example, we cover three basic things when describing Emissary to our community: the what, the how, and the why.

The What: Emissary is a sales intelligence network of 6,000+ former executives from the F1000, primarily from the IT and Marketing chains of command (tailored to the prospect’s relevant buyer titles).

The How: Emissary connects our client’s enterprise sellers with former decision makers from their target F1000 accounts to help them: (1) find and open net-new opportunities, (2) accelerate and close existing opportunities, (3) expand landed accounts, and (4) provide exclusive insights for ABM/Marketing initiatives.

The Why: We want our client’s to be able to tap into the years and years of experience these senior executives have at the largest and most complex organizations in the world. We want your sellers to be able to access the tacit knowledge, and non-commoditized information, that they can’t find anywhere else to help them move the needle with their high-priority accounts – whether that is in setting a net-new meeting or closing a deal.

We also like to set expectations ahead of time by framing the conversation with a single, simple number. For example, I’ll start a conversation by saying “I’m going to talk about three things today.” The same works well for concluding the meeting: “My takeaways from today’s call were two things: x and y. Anything you wanted to add?” In keeping it simple and easy to remember, both parties are set up for success as everyone will be on the same page.

Focus on the deal

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We’ve often found that sellers go into a conversation thinking they need to sell a deal a certain size or in a certain way. But our CRO Eric Rosenthal once said something that has stuck with me since: “Don’t sell it the way you want to sell it. Let them buy it the way they want to buy it.”

What he meant is you need understand how your prospects think and why they’re thinking that way. Then position yourself accordingly in order to make it as easy as possible for them to buy when they’re ready to buy. 

Look, we get it: you want to close the biggest deal possible. Every salesperson dreams of landing that multimillion-dollar, enterprise-wide deal. And while those deals certainly happen, moving a massive deal to “yes” can take months—and with far more stakeholders involved, there’s a much greater risk of the deal falling through entirely. And often, a prospect just isn’t ready to commit to a deal of that size.

Pilots are perfect for these scenarios because they allow your prospects to decide exactly how big of a deal they’re ready for. Once they’ve seen what your product or solution can do, they’ll be ready—probably even eager—to sign a larger deal. I’ve also found that prospects who start with a pilot can become your biggest advocates internally and help you expand to other lines of business, largely because you built trust and didn’t pressure them into a deal they weren’t ready for.

It all comes down to understanding what your prospects want. For example, it took both LinkedIn In-mail and a lot of texting to get my second to last deal across the line. For another recent deal, it meant working until almost midnight Friday at the end of a quarter, because the prospect was based abroad and it was 6:00 a.m. their time. But that’s the way the prospect wanted to get the deal done, and that’s how we got it done.

Follow up effectively

Believe it or not, it seems like the vast majority of sales people don’t do the easiest thing they can possibly do to close pilots—or any deal, for that matter—and that’s following up.

This isn’t rocket science. Just follow up until you understand your prospect is either going to buy, not going to buy, or might buy at a later date. I consistently see sales reps failing to follow up, and it baffles me. At Emissary, we work hard to ensure that our sellers take a consistent, thoughtful, and tailored approach to follow up. Unfortunately, not every sales team operates this way.

Remember, your prospects are starved for time and have countless people and tasks competing for their attention. Just because they didn’t get back to you right away doesn’t mean they don’t have want and need what you’re offering. I can’t count the number of times I’ve heard people say, “Thank you so much for following up with me. I have a million things going on, and if you hadn’t followed up, we wouldn’t be here.”

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Executive Insights

When you have simple, memorable messaging, the flexibility to allow buyers to purchase on their time and their terms, and the determination and patience to follow up effectively, you can easily sell more pilot deals and exceed your quota.