This essay originally was published on April 13, 2023, with the email subject line "CT No. 163: Final_v5_FINALfinal_365."

by Deborah Carver

I’d finally done it: I’d written the perfectly optimized landing page. The audience couldn’t possibly miss the message, and I was confident the client would see results. Each keyword was meticulously incorporated; each verb hand-selected with a craftswoman’s care; each sentence constructed with impeccable, near-poetic syntax. The gestalt deftly hit every request in the creative brief. Pour me a whiskey and call me Don Draper: barely a year into my first agency job and I’d already mastered the assignment.

I set off across the office, hoping to catch the account’s media director as he traversed the office between meetings. His approval was the crucial final step before it was sent to the client. During our standup two hours earlier, he had expressly hoped I’d finished it already, but my official deadline was the day’s end, and I needed the extra time to navigate the tricky subject matter.

Holding my laptop with the excitement of a puppy sharing a chew toy, I presented my work. He looked at my screen, nodded and smiled. “We’ll iterate,” he said, “and you can just email me next time.”  Then he disappeared into another conference room.

I couldn’t tell whether the feedback was good or bad. “Iterate” certainly wasn’t a word I’d used in my previous ten years of editorial experience. It wasn’t a verb I recalled from journalism school, overheard at my book publishing internships, or bandied about at the web B2B editorial gig where I’d excelled previously. I knew what “reiterate” meant, but even with the “re” it didn’t track. What exactly did he mean by “we’ll iterate”?

I did what any adaptable performance marketing newbie would do: I Googled it. Every definition in the blue links mentioned the word “repetition” or had something to do with mathematics. Try as I might to apply it to the craft of web writing, I came up empty-handed. Either it didn’t mean what he thought it meant, or I was being completely obtuse.

Nearly a decade later, I realize it was a little bit of both. What the media director was trying to say was that not only did he want to make light edits to the language, but he also wanted me to think of a future where mine wasn’t the only version of a landing page produced for the campaign. He wanted me to be open to developing other options to feed the algorithms.

Simply put, iteration is a repetition of a process to solve a specific problem, and it’s a big part of how machine learning algorithms are developed and optimized. Iterations are helpful when you have identified a process's elements (such as a website and money for an ad campaign) and a clear result the elements are working toward (such as 20 new users in one month).

Iterative processes let computers figure out how to connect one end of that equation with the other. Like optimization, where resources are focused to create the best path to fulfill a prime directive (usually form fills, button clicks, engagements, etc., unless you’re Robocop), iteration is a term for a computer process that’s now applied to content production.

Iteration is familiar in software development and data science, and it’s embedded in the production methodologies and business models of the internet: development processes like Agile and GIT and books like The Lean Startup advocate for rapid, repetitive testing of digital products. Some in tech believe that as long as you have the distribution mechanisms (the ad network or an ad store) and the product framework (an ecommerce website or an app), it’s only a matter of iterating different versions of creative content until you find the winner. If you test enough versions, ultimately you’ll find one that makes money.

Among the venture capital buoys of performance marketing in the 2010s, where tech companies owned both distribution and product, the digital experience was so novel that nearly any content would perform. In this business bubble, my media director colleague saw iteration as the first step to discovering both small, incremental gains and large leaps forward—the kind of digital performance that excites growth hackers and executive types.

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