Disorder And Improvisation: How Amazon's Chaos Shapes Its Products

How did Amazon devolve into a company that trapped Prime subscribers? Consider its lack of UX design and copywriting, our new Big Tech Insider columnist writes.

Today at Big Technology, we’re debuting our Big Tech Insider column, where experts with unique insights about the tech giants— and experience within them — tell the story behind the headlines. We’re starting with a three-part series by Kristi Coulter, a longtime Amazon veteran, who will take us inside the company to decode its mysteries. Coulter’s latest book, Exit Interview, is filled with revealing stories about her time at Amazon, and she expands upon that work here.

I’m thrilled to publish this story today. The entire series will be available to paid Big Technology subscribers, and this is a preview for everyone.

We’re running our paid launch special for one final day. You can sign up here:

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And now, here’s Coulter’s debut story on Big Technology:

Disorder And Improvisation: How Chaos Rules The Day at Amazon

By Kristi Coulter

In late June, the Federal Trade Commission accused Amazon of tricking customers into signing up for Prime, and trapping them once they got there. The company’s signup language was vague, and surprised people into a year of Prime after an amorphous ‘free trial.’ Canceling required navigating a torturous number of screens and answering questions in the spirit of, “Are you sure you don’t not want to not cancel Prime, or yes?” The internal nickname was Project Iliad, evoking Homer’s labyrinthine poem about the decade-long Trojan War. It was a mess, and an apparent betrayal of principle from a company fixated on ‘customer obsession.’

I spent twelve years at Amazon, and I know what most outsiders don’t: Underneath its smooth-looking service, there’s a startling level of disorder and improvisation. So my first thought upon seeing the FTC’s complaint was Hmm, maybe refusing to hire designers finally came back to bite them. What may look like lockstep planning at Amazon is often a blend of frantic effort, hail-mary passes, and pure chance. It’s a testament to the company’s execution that the public underestimates the chaos factor. But it’s there. And impossible-to-navigate signup flows are a direct result.

Let me take you inside Amazon for a moment. During my tenure, company leaders used words like “fluff” and “puffery” to describe disciplines like design and copywriting. The site was bare-bones on purpose, so customers could shop without wading through slow-loading pages or annoying pop-ups. Our copy was also functional to the extreme. The vendors who paid for promoted ‘co-op’ weren’t thrilled with our austerity. Other online retailers provided them with beautiful custom campaigns, while at Amazon even a holiday graphic was just a regular product shot with a sprig of holly slapped on it. As we explained it, our customers cared about value, selection, and convenience. They could go elsewhere for beauty or witty language.

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It’s a perfectly valid stance that unfortunately overlooked a couple of key factors. One is that graphic and user experience (UX) design are totally different things, and while pretty pictures are arguably optional, clear and intuitive customer interactions are not. And yet the entire site was supported by just a handful of UX designers, even as we expanded worldwide and added a steady flow of new widgets and features. Everyone I worked with took Amazon’s Customer Obsession leadership principle quite seriously, but this felt like a blind spot.

Amazon also failed to recognize that UX design and copywriting were real jobs requiring special skills.As head of site merchandising, I had a close view into everything that could go wrong when non-professional writers were tasked with communicating to tens of millions of Amazon customers: Fisher-Price spelled “Fisher-Prize,” an email promising 30% off in the subject line and 10% in the body, carnival-barker “HOT DEALS!!!” come-ons. But every time I made a case to senior leadership for hiring trained pros, I got the same response: anyone with a college degree should be able to write flawless copy, and without the help of a proofreader.

“But even Pulitzer prize-winners aren’t flawless,” I argued. “Even Philip Roth gets proofread.” The shrug I got back said that, well, this Philip Roth person apparently wasn’t Amazon material.

I had an internal side gig on the Customer Experience Bar Raiser program, which allowed any team launching something new to get feedback from a fresh and dispassionate set of eyes. To mimic the customer point of view, I ran my reviews by projecting the site onto a screen and simply talking out loud as I tried to use the new feature. I set up a baby registry for my fake future child, tried to buy the right edition of a used textbook for my fake education, sent a real Southern Living gift subscription to my real mom.Any time I found myself saying “I don’t understand this sentence,” or “Wait, what do I do next?,” I already knew what the response across the table would be: a pained look and an explanation that a product manager had designed the UX, or a developer had written the copy. It’s not that the team didn’t care, but in a company so allergic to “fluff,” DIY was often the way to move forward, and not moving forward was not an option.

I saw our chaos misread externally as intentionality, partly because a segment of the public views Jeff Bezos as a Lex Luthor-tier supervillain and partly because Amazon did so many things well that customers forgot it was run by human beings who could screw up. And with all the headlines about our skyrocketing employee count, it probably didn’t occur to many outsiders that we were skimping on the UX and editorial roles needed for a coherent site experience. When hundreds of LGBTQ+ books were removed from Amazon sales rankings, conspiracy theories sprang up about Amazon bending to right-wing demands, though in truth it was pure user error in an environment where a frightening number of people could make direct changes to the website.

When George Orwell’s 1984 disappeared from thousands of Kindles, blogs speculated that like Big Brother, Jeff was reminding readers he had ultimate control over their access to books. The reality? A copyright violation, plus a removal policy that had not been thought through. (That the book in question had to be 19-freaking-84 was, we assumed, a cosmic joke.) These days, when I’m scrolling through endless sponsored ads on a product page, or wondering why my search results are so unhelpful, I wonder if it’s because Amazon has deliberately prioritized ad dollars over shopping experience, or if it simply isn’t anyone’s job to worry about that so-called fluff.

Shortly after my first read, the FTC added details to its Prime filing that makes the misdirection sound highly intentional, and upheld by VPs despite fervent protests from rank-and-file employees, including UX designers. (Thanks for trying, you guys.) The bad behavior had to start somewhere, though. Amazon created an opening that led to a game of “chaos or evil?” And sometimes, in that game, evil wins.

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