The Suckification of Tech

How the Trouble With Customer Success Explains the Trouble With the Tech Industry

Photo by Tara Winstead

Inside every company, there are two wolves: a promise-making organization (marketing, sales, product) and a promise-keeping organization (engineering, support, success). In other words, one is an initial-revenue engine; the other is a value-fulfillment and recurring-revenue operation.

In a sustainable company, these systems are symbiotic. The revenue creation part of the organization makes reasonable and likely-to-succeed promises to its prospects and customers, while the value fulfillment operation is resourced in a way that makes mutual success and customer satisfaction probable, if not inevitable. If reality doesn’t live up to or exceed expectations, existing customers will not buy again and the company’s poor reputation will eventually dissuade new customers from buying at all. 

It’s the first part of that equation—existing customers becoming repeat buyers—that makes any sustainable subscription model work, software or otherwise. Anyone who’s worked in tech can recite this axiom as if it’s an article of faith: it is much more efficient to earn repeat business from existing customers than it is to spend money on acquiring new customers. 

Therefore, in a market-based economy, businesses have a vested interest in delivering on the promises they make. The two wolves—the promise-makers and the promise-keepers—are part of the same pack.

How the Tech Industry Achieved Escape Velocity

Yet many high-growth software companies have found a way to evade market dynamics. Propped up by billions from venture capital, private equity, and sometimes public markets, they can sustain enormous operating losses while pouring money into massive marketing budgets and highly paid sales teams.

Customer attrition, even when severe, is the ultimate lagging indicator because annual and multiyear contracts prevent customers from leaving until renewal, staggering churn over time. The big bet is that even a large hole in the bucket can be overcome by pouring piles of money into sales and marketing, aided by a little accounting artistry. Most tech companies foreground gross margin, a measure that excludes the enormous cost of acquiring replacement customers by classifying sales and marketing as OpEx, as though those expenses were incidental rather than fundamental to the business model.

This dynamic turns capital investment into the equivalent of a castle siege: whichever company can outlast their competitors by outspending or acquiring them captures the spoils (i.e. market dominance) with the commiserate destruction being business as usual.

Cory Doctorow’s observation in Enshittification is that market dominance is only phase one. Once consumers have few meaningful alternatives, companies can begin turning the screws on both individual users and business customers. Consumer lock-in is where the real value extraction begins.

In order for investors to get their ROI, the margin has to come from somewhere. So there is pressure to degrade the product or service in some way, little by little, and then all at once. At first it’s just a few small nips. If desperation or overconfidence (or an unholy combination of both) sets in, then comes the wholesale bait-and-switch. The company continues to trade on expectations established under the old social (or literal) contract while quietly and unilaterally rewriting its terms.

Original Sin at the Point of Sale

That’s not so different from the strategy many mature companies, within tech and beyond it, employ once more organic sources of growth slow: degrading the customer experience to eke out a few more points of margin (“shrinkflation” being a common example). Not that we should be complacent about it—that still sucks. But I suppose one could argue that, before enshittification set in, there was once a plausible exchange of value for money.

Yet it’s my observation that many business tech companies still in the early innings of growth have stopped waiting to pull the rug. The rug is missing, full stop. Many executives and investors seem to have stopped even pretending that the companies they are building are anything more than financial speculation machines. That is a very different mindset from trying to build the best or most widely used product in its category, and then making a ton of money as a result.

Many tech workers, especially those in customer success and support, feel demoralized and exhausted from being forced to uphold half-truths—and sometimes outright lies—made by the company’s promise-makers. Customers are ensnared from the very beginning and are then rewarded by half-hearted and absurdly under-resourced attempts to deliver on what they bought. With business software, customers often discover the truth during onboarding, or even later, when they finally gain the access and context that would have helped them make an informed purchasing decision.

It’s this shadow puppetry, the careful manipulation of what customers can see and when they can see it, that makes me believe that those of us on the promise-keeping side of our organizations are uniquely positioned to explain why the tech industry feels so gross and so disappointing in this moment.

The Trouble with the Customer Success Function is the Trouble with the Tech Industry

In the essay series that follows, I’ll examine how the separation between promise-making and promise-keeping shapes the software industry, and how the disempowerment and devaluation of the promise-keepers reveals the industry’s casual disregard for its customers and employees alike.

First, I’ll look at how revenue creation and value fulfillment are different systems; how the timeline for success in those systems determines authority; and how authority and accountability flow in opposite directions.

Then I’ll examine why Customer Success teams are being pressured to stage increasingly visible displays of commercial contribution, despite having responsibility if not accountability for retention and growth. This mandate creates increasing amounts of internal pageantry at the expense of the long-term, preventative work through which recurring revenue is actually earned.

Finally, I’ll explore what is lost when promise-keeping is placed under the authority of promise-making. How the people who sell a financially legible representation of value gain authority over those responsible for making that value real. Yet that doesn’t resolve the tension between selling value and delivering it productively. It resolves that tension by removing one of the company’s last independent checks on the gap between what customers were promised and what they actually receive.