The big whale and the long tail

Main illustration: Vivian Shih

In “Moby Dick”, Ishmael is taken by Captain Ahab’s quest to seek revenge on the whale that took so much from him. Most sales reps, myself included, possess a degree of Ahab’s thinking.

We obsess over closing the deal no one says we can, the white whales, and too often neglect the long tail of school fish that are abundant and easier to catch.

Let’s say two new deals come into your pipeline: one for an early-stage startup, which we’ll call Tiny App, and the other for Apple. Most salespeople, myself included, would drop everything and start talking to Apple. After all, how many Tiny Apps would you have to close to reap the same amount of revenue Apple would bring? Deciding where to prioritize your time seems obvious, but we’ve found that the opposite is the way to go. If you knew Apple was worth $100k ARR and took a year to close and Tiny App will be max $10k ARR but could close in two weeks, would you re-prioritize your deals? Add in the fact that there are many Tiny Apps you could close in the year versus one Apple, plus the higher likelihood of closing, and I hope my point is getting clearer.

We’ve developed a sales process which involves closing small deals fast and first so we can spend time on the larger and more complex ones.

White whales cost more to catch

In sales we usually optimize for one metric – revenue. How can we drive the most amount of revenue to our company? Catching a big whale results in a big pay day for your company (and yourself). If your goal is simply to bring in revenue, focusing on potentially high value activities seems to make the most sense.

We’re able to spend more time working larger deals by changing the way we work smaller deals.

However, an oft-overlooked metric is time-to-close. The bigger the deal size, the longer the sales cycle and greater the complexity. There’s more people involved, more processes and functions to navigate (for enterprise prospects, we’re talking security, legal and the sales rep’s kryptonite, procurement). Instead of just convincing a single decision maker, you need to convince multiple teams that what you’re selling will have a net positive impact. This means in-depth discovery (sometimes with more than one team on more than one occasion), numerous product demos, extended trials and pilots.

It’s impossible to suggest one process above another when selling to larger accounts vs. smaller prospects. However, we’ve found that when we optimize for speed for potential customers at the smaller end of the market and thoroughness at the top of the market, both conversion rates and overall revenue benefit.

Optimize for response time at the lower end of the market

For a smaller opportunity, the speed of your first response is a crucial step to convert these opportunities to revenue. Small companies are typically nimble and agile. They can install and evaluate software quickly. Coupled with the advent of modern messengers on many marketing sites, and it’s never been easier to buy a product.

From a sales point of view, it is important to assist these customers in their evaluation and not stand in their way. By focusing on responsiveness and providing the right material to help smaller customers evaluate, not only are you matching your sales process with their buying needs, you’re also saving yourself to focus on those bigger prospects.

At Intercom, we’ve aimed for the holy grail – a real-time hand-off after qualifying the prospect to the introduction of their dedicated sales rep (at Intercom, that exchange happens between frontline sales development reps and account executives).

We do this to move smaller prospects from their initial potential interest phase to a full product evaluation as soon as possible. We use our own live chat for sales product to seamlessly transfer conversations from one person to another, with no friction for the end user.

Scaling for speed

Once this happens, account executives focus on enabling small prospects to do what they do best – make quick decisions and move fast. After all, your contact at a startup might be the decision maker, the day-to-day user, even the installer. Do they really need a full systematic sales cycle with a discovery call, multiple demos, etc.? Is it beyond the realm of possibility that you could get a contract signed on that same day? Sales should be there to add value, not roadblocks.

Once the prospect is evaluating your product, marketing automation becomes your friend.

How do you do this? Think scale. In the earliest stage of a sales cycle, having a content bank is key. You can send Tiny App a relevant customer story, a best practice guide for their use case, or simple install and setup instructions. You’ll be surprised what impact a custom 20-second video has with your prospects.

Once the prospect is evaluating your product, marketing automation becomes your friend. There are certain steps that every prospect will have to take to see value from your product. Is a salesperson’s time best spent individually showing similar customers the exact same feature? We’re finding that this content is best delivered in a messenger, when they’re on your site or in your product, rather than more traditional channels such as phone, video calls and emails.

Using these different tactics, we’re moving more efficiently than ever. We’ve been closing more deals faster and freeing up time to devote to potentially higher impact/reward activities. In short, we’re able to spend more time working larger deals, not by neglecting, but by changing, the way we work the smaller deals.

Cast a wide net (before you go whaling)

How many meetings/months will it take to even find the right person in Apple to get one script of code installed on a tiny function of one of their many products? The fact is that there’s a direct correlation between contract value and time to close. Going after a large prospect is a whaling journey. You need to prepare and plan your moves meticulously. You need to deep dive in your discovery, formulate a business case and advocate the merits of your product. You need to mobilize internal teams for these customers too. All of this requires time. To give yourself time, as somewhat counterintuitive as it seems, trawl for the small fish first – and the whales will follow.