We all want to be a large deal closer. We all want a high-five from the CRO and a standing ovation from our colleagues for saving the quarter by landing a last-minute whale. 

We all want a lot of things, but they may not always be what’s best for us—or for our revenue teams. And sometimes, that includes landing the whale. After all, if old Ahab had had the sense to go after smaller, more attainable game than the fearsome Moby Dick, he could’ve walked away with his leg and his life. But he was so focused on landing the big one that he lost literally everything in the process.

Putting all your effort into closing the big one can be unnecessarily risky. Sometimes, the smarter play is to be flexible and start with small deals, even with the largest enterprises. And in terms of revenue, a number of smaller deals that close quickly and blossom from there can easily bring in more ARR than a single massive sell. 

Here’s how to make it work.

Starting small doesn’t mean you can’t think big

Let’s be clear: we’re not suggesting you should content yourself with selling a Fortune 500 on a small contract with two users and call it a day. Quite the opposite. In fact, starting small, letting a small group of users learn the ropes and find value quickly, and working out the kinks as soon as possible can provide a valuable foundation for a much larger, more lucrative engagement down the line.

“Trials and pilots give buyers the opportunity to see more about the actual service,” said an Emissary and former VP of IT at Kellogg’s. “Based on that, you can determine if you can go at a regional or global level for a solution. That’s really helpful before you’re signing a global deal.”

As we’ve mentioned, this approach can also be ideal for identifying and addressing challenges related to implementation, like difficulty with data migration. It enables you to solve them on a smaller, more manageable scale—and one that’s less visible to the enterprise at large. Once your prospects dig in and start to see ROI on their purchase, it’ll be much easier to ramp them up and expand the engagement across new teams or LOBs. And if you can know in advance which stakeholders are likely to find the most immediate value, you’re even more likely to land-and-expand than going in blind.

Jodi Watson, former CMO of Petco, is a staunch advocate for this approach, noting that vendors should avoid trying to “boil the ocean” right away.

“You should start small, and you should demonstrate that when you do, your customer can get immediate value out of the engagement in a very low-stakes situation,” she said.

Get creative to close quickly

Starting small doesn’t just give you the chance to break into an enterprise more easily than a major global deal. It also gives you the opportunity to provide innovative, customer-friendly pricing models, as well.

“If it’s possible to offer a proof of concept that either puts skin in the game for both the customer and the vendor or doesn’t cost anything for the customer, it’ll be a win-win,” Jodi said. “I think performance is a big deal, and if your solution helps me exceed our goal, I’m going to be willing to pay you more. If we don’t, I would like to see some kind of rebates from the vendor.”

She pointed out that these kinds of performance-based agreements are becoming increasingly important and that companies are starting to look for more so-called  “guarantees” with performance-based metrics in place.

This can be the perfect angle for selling in a small deal: if your solution helps the customer hit a predetermined goal, they agree to a longer or larger engagement. If it doesn’t, the customer is entitled to a refund—or perhaps no charge at all.

Jodi also pointed out that smaller deals have the opportunity to alleviate the IT and procurement headaches that often come with larger enterprise contracts.

“If there’s a way to implement a solution that can do an end run around IT, at least to some degree, that makes the deal a lot more attractive,” she said. “IT has 100 ‘number one’ priorities, and I’ve heard ‘I can’t do that because IT doesn’t have the resources!’ a million times in my career. If there’s some way that we can at least get some kind of proof of concept or testing going, that helps the customer tremendously.”

Where do you suggest I start?

It’s clear that starting small is often the most effective way to break into net new accounts, but that doesn’t mean it’s a piece of cake. How do you identify the ideal project to start with?

When determining a starter project, don’t look at one single line of business and think that’s where you need to be. Instead, Redhat suggests taking a strategic approach to selecting a pilot project.

Make it your priority to learn about the “IT organization’s strategic initiatives for the next few years and pick one initiative that can act as a prototype. Be successful at it, don’t look back, and keep scaling workloads.”

When it comes to cloud solutions, for example, Allan Brearley, cloud practice leader at ECS, says “suitable pathfinder candidates might be an application currently hosted on-premise that can be migrated to the cloud, or a new application/service that is being developed in-house to run in the cloud from day one.” Start with the applications that consume the least amount of resources, like compute, storage, and network. These will have the lowest impact and take less time to migrate.

Regardless of what type of solution you’re providing, the idea is to identify an entry point that maximally illustrates the benefits of your offering while exposing your prospect to limited risk.

Deal Closer Tip: Sell how they want to buy

Once you determine what project you’re going to pitch, it’s time to decide how to sell the project. Emissary sales director Curt Clauss has a philosophy on how sellers can generate more pilots effectively.

One of the biggest takeaways from his piece stems from the sage advice of Emissary CRO Eric Rosenthal:

“Don’t sell it the way your want to sell it. Let them buy it the way they want to buy it.”

Curt notes that this approach requires sellers to remain flexible in the sales process and understand that today’s buyers are inundated with sales pitches and, even if they love your solution, they just don’t have the time to commit to a high-intensity sales process.

If your prospect seems particularly harried and balks at the notion of getting a large deal past the decision-maker and through procurement, consider scaling it back.

Buyers often have thresholds below which purchases of services and software don’t require the same rigorous approvals process as a typical enterprise deal. This allows you to get in, demonstrate value, and plan for expansion without the headaches that come with a large deal closer.

All told, there’s a lot of value in going after smaller deals when opportunities arise. It doesn’t mean you have to abandon your hunt for the white whale. But when an enterprise deal looks dicey at best, pivoting to a pilot or a more limited engagement can mean the difference between an account that’s primed for revenue growth—and no revenue at all.

Executive Insights

Breaking into your top accounts is tough, and it can be doubly difficult if you’re dead set on doing a major enterprise deal or nothing at all. But if you understand both the immediate and long-term value of smaller deals and are willing to be flexible in your terms, you can be a deal closer, delivering  more revenue and increasing trust and customer satisfaction with a lot less difficulty than traditional enterprise deals. Food for thought.