Is sales the personification of the Sisyphus punishment?

According to the myth, Sisyphus, a character in Greek mythology, was punished by the gods and forced to roll a massive boulder up a hill, only for it to roll back down each time it neared the top. This cycle of futile labor was meant to last for eternity, symbolizing endless, pointless effort. This myth has given rise to the term "Sisyphean task," referring to a task that is both laborious and futile. But what does this have to do with the sales department?

The sales department carries the responsibility of lubricating the business’s system, creating the input that pushes the productive system into motion to deliver the output (a product or a service). This profession is often perceived in a very binary fashion by the uninitiated, with salespeople labeled as either good or bad at their trade. But what does this have to do with Greek mythology?

Every sales cycle is the same, no matter what scale you look at it. When you engage in outreach—whether sending an email, picking up the phone, sending a Loom video, poking people on LinkedIn, or even sending smoke signals—you are pushing that boulder uphill one stage at a time. You qualify prospects, pitch to them, sell to them, and hope to close the deal. And when that cycle is over, you must start again. The same goes for time cycles—sales divisions operate on a target timeline, pushing that boulder up to meet targets, only to see it roll down to zero for the next budget. Ironically, Sisyphus's hill remains the same, while sales targets only go higher.

I may have painted a rather bleak picture of the sales business, but that isn't the aim of this article. What I want to bring to your attention, dear reader (especially if you work in sales), is the very predictable, systemic nature of sales. Sales is cyclical, with repeatable patterns, tasks, and heuristic outlooks. Sales is a combination of churn rate—how many leads you can talk to—and odds—how to increase the probability of a prospect wanting to buy what you sell. Sales is very much built around heuristics and feedback: if you pick up the phone (input), the outcomes are as follows: you either successfully pitch, are told to take a hike, don’t get an answer, or find the line is dead. The kind of responses you get provides feedback that you can then use to fine-tune your input.

Unfortunately, my inbox is full of salespeople who seem unaware (or unwilling to see) these patterns, focusing either on quality or quantity, when the real edge is trying to generate marginal productive gains by incorporating elements from the opposite spectrum. If you lean toward the qualitative approach, you’ll spend a significant amount of time and energy preparing your outreach and pitch to increase the odds, but at the cost of your churn rate. If you lean toward the quantitative approach, you’ll spend less time and energy preparing your outreach and pitch.

For example, I am constantly approached by hopeful salespeople trying to sell me a certain kind of financial product (IYKYK) that I categorically do not want because I already have it! That’s a Sisyphean task if I ever saw one. This same business reaches out to me every quarter (I guess their full cycle churn rate is 90 days), and every quarter I have the same answer: "No, I’m already your customer." Now, this is where an evident marginal gain could be made. Rather than spend zero energy and time preparing that outreach, the salesperson should edge slightly toward quality by checking their CRM to see that I’m already a customer. They should be dialing an actual prospect (a business on that side must have one—if not, here’s a free lead for you, fine people of sales CRMs). This is a marginal gain that would benefit the business by eliminating duds, existing customers, and dead ends from its market.

From an individual’s perspective, it would tremendously boost the salesperson’s morale to know they’ve decreased the odds of being turned away within seconds. From a department’s perspective, you’re getting a realistic territory, and from the business’s perspective, you avoid frustrating your existing customer base. In effect, glancing at your CRM before dialing me would cost you a couple of seconds but would, over a long period of time, increase your efficiency (I’m not the only customer they’re dialing).

My inbox is full of messages from businesses selling services or products I don’t remotely qualify for, for very evident reasons (geography, nature of my business). While I can understand that some send mass waves of emails, most are individual salespeople focusing 100% on quantity and 0% on quality. If you can’t name my business, describe the nature of my business, or insert any relevant information directly related to my trade, then the Cialdini principle of reciprocity will come back in full force: you’ve spent zero energy and effort reaching out to me, so I will therefore spend zero energy in return to answer you.

The law of sensitive dependence on initial conditions (or more commonly known as the butterfly effect) is one of the biggest helping hands as a head of sales. Those small variations in the initial conditions of a complex system like sales can lead to vastly different outcomes. In other words, in chaotic systems, even the tiniest difference at the beginning can produce unpredictable and significant changes in the long term. Just as Sir Dave Brailsford pushed the national cycling team of the UK from zero to heroes in five years (by winning more gold medals in one Olympiad by a factor of ten compared to the past 90 years) through constant marginal gains, we as salespeople should always aspire to pull our qualitative or quantitative inputs toward the opposite.

Finding these nuggets of small improvements might not seem like a big change at first, but the compounding effect of consistency and time works just as well in our trade as it does in a savings account. Sales isn’t an art; it’s a science.

For the salespeople out there—which end of the spectrum are you on (quality or quantity)? What marginal gains do you apply? For the marketers being approached, what are your eye-rolling moments?