Apr 16, 2014 · 3 minutes

Five years ago, Jordan Kretchmer, Founder and CEO of commenting platform Livefyre, had an idea he thought could revolutionize online discussions. Instead of a single comments box at the bottom of a webpage, readers could comment on any line or word in the text. "The only reason we didn't explore it was because we didn't have much traction in the market yet," Kretchmer says. "We didn't want to change the paradigm of how comments worked at that time."

In the years since, Kretchmer's vision of an annotated Web has been realized, but only on a few sites, like RapGenius' massive anthology of hip-hop lyric explanations, blogging platform Medium, and the Atlantic Media's business news site Quartz.

With today's announcement of Sidenotes, however, Kretchmer can finally spread these annotation tools to the hundreds of thousands of sites and blogs that rely on Livefyre's commenting platform (including Pando).

"We're on over 650 paying sites on the Web," Kretchmer says, meaning 650 outlets pay Livefyre for its premium service. "100,000 bloggers are using it for free. We finally felt like we were in a place where we could lead a change and force users to consider this new kind of interaction."

The basic mechanics of Sidenotes are similar to those used by Medium: Users simply highlight a line and a comment box appears. Existing in-line comments appear off to the side in the margins of the text. (Click here to see it in action). But while Sidenotes' logistics may feel familiar, what makes today's announcement significant is the scale at which Livefyre can bring these tools to the Web.

"It's the first-ever enterprise-scale product for delivering annotations," Kretchmer says.

Crucially, Sidenotes also updates in real-time --  you don't have to refresh the page to see new comments. This makes online discussions akin to chatting or messaging, so they feel less like shouts into the abyss and more like real conversations.

The final piece of the puzzle is mobile. People say commenting is broken on desktops, but on mobile it's a total nightmare, from unusable interfaces to sites that don't even try, removing comments altogether. With all the messaging and social sharing users do on mobile, it's perhaps surprising that commenting platforms have failed to keep pace. Sidenotes attempts to rectify this as well with an interface that lets you expand and collapse comments at any point while reading, then shuffle through them by swiping.

All told, Sidenotes is an ambitious attempt to reinvent the way we talk about and around content on the Web. But it does beg the question: Will commenting sections still play a big role in the future of online conversations? Last year, Popular Science created a minor stir among media thinkfluencers when it shut off comments. Meanwhile, Some of the buzziest new sites on the Web launched without comments, including Andrew Sullivan's The Dish and Vox.com (though comments are reportedly coming to Vox in time).

At Nieman Lab, Joshua Benton explains why some sites have killed or deemphasized comments:

I feel like “some news orgs are abandoning comments” is a story that could have been written on any weekday since 1999, but there really is a larger trend at work here around social sharing serving as (a) the place where your readers can sound off, but (b) a way to do it away from your site and (c) a way to do it that actually drives more traffic to your content.

Indeed, it's easier to let other platforms like Twitter or Facebook deal with the headaches of spam or hate-speech. Livefyre's moderation tools are pretty extensive but they still require buy-in from someone at a news organization. And with so many people talking about content on other networks, commenting systems may only distract from those social activities. A story may have 100 comments but it does it really bring value if it's the same five people arguing back-and-forth?

Kretchmer would argue that when comments fail it's because of the commenting platform and not an issue endemic to comments themselves. And in defense of Sidenotes, annotations have been fairly well-received: Just look at the success of RapGenius. Livefyre and Sidenotes also allow users to customize comments from one story to the next, so discussions can be turned on or off depending on the nature of the piece.

Now that Sidenotes is built and launched, here comes the hard part: Making sure it scales bug-free.

"With enterprise business (companies) pay us a lot of money to make sure it's super-flexible. It has to work in every scenario imaginable and on every CMS. There's a lot under the hood here to make it scale with that kind of usage."

Of course, "too many users" is never a bad problem to have.

[Illustration by Yau Hoong Tang]