Hey, I Need to Talk to You About This Brilliant Obama Email Scheme

The Obama campaign raised $690 million online. The majority of it came from the fundraising emails that peppered inboxes for the last two years. They employed a team of 20 writers and a sophisticated analytics system to measure and improve their effectiveness. Now, they're starting to spill the secrets they learned during the campaign. And as revealed in a new report from Joshua Green*, there was a high-powered viral media outfit lurking in Chicago.  The lessons from the campaign aren't just a recipe for making money, but for winning eyeballs in the brutal deathmatch to grab your attention on the Internet. What we can learn is how the Obama campaign fine-tuned its content for maximum Internet impact, i.e., how it channeled its inner BuzzFeed.

As a digital media person, I recognize a lot of these tricks, but their content doesn't really change ("Money, plz, kthx."). Hold that variable steady and it becomes a lot easier to test what online media works and what doesn't. 

First, let's propose that your inbox is a publication. It's a weird publication to be sure, assembled from your mom's emails, your friend's quips, some chat boxes floating in the right hand corner, daily deals sites that you must have signed up for at some point, various digests, some news alerts, and that thing you've been meaning to deal with for months but haven't. So, this reverse chronological publication is always available for you, and you know there are some things you'd like to read within it, and many more that you'll flip by and/or delete. 

The first step for the Obama campaign was to grab your attention long enough to get you to open the email. So, they got casual. "The subject lines that worked best were things you might see in your in-box from other people," Toby Fallsgraff, the campaign's email director, told Green. "'Hey' was probably the best one we had over the duration."

Tone, on the Internet, is everything. Unlike a magazine where you know what tone to expect (magaziney!), writing on the web is all jumbled up. I think people get really, really good at detecting if pieces of writing on the Internet -- be they emails, blog posts, tweets, or Facebook updates, Google ads, YouTube comment threads -- are meant for them or not. And the key signal is how you put the words together. The tone tells you who the implied author of the work is. And that's how you answer the eternal question, in a inbox of infinite sentences, would I like to read this person's? 

Of course, like everything else in the Obama campaign, this process was a cyborg. Humans input the initial emails, but machines sorted the best from the worst. Here's how Green described the process: 

The campaign would test multiple drafts and subject lines - - often as many as 18 variations -- before picking a winner to blast out to tens of millions of subscribers.

What I learned in my own reporting was that the worst-performing letters in that testing process only generated 15 or 20 percent as much money as the best performers. The analytics allowed them to only send emails they knew worked. 

But perhaps the most interesting and crucial part of the Obama camp's email strategy was that it was not static. They didn't find that the "Hey" subject line worked and then stop there. Their analytics told them that every subject-line technique, every tonal quirk, had a limited shelf life. The well ran dry almost as soon as you'd divined its location in the psyche of the Democratic base. 

Once more quoting Green:

In my experience in the content game, nothing has proven more true. Any detailed social media primer I give you would be out of date by the time I could finish writing it. Any operational headline writing strategy would stop working if everyone used it. Everyone clamoring for your attention on the web is trying to strike that perfect mix of familiarity and novelty. And that means the content techniques that work are necessarily recursive. You change what people like by doing whatever you do. Which then requires that you do something else, which then changes their tastes again. 

This is true for your core donors (or readers) as well as the farther flung people who might only get forwarded your fundraising email (or story) every once in a while. Sometimes, I start to think of the Internet as a gatheration of starlings, each reader/writer moving in response to her immediate content environment, and somehow the whole thing seems to move together, following a million different versions of the same core set of rules.