Grammarly writes a new corporate playbook

When San Francisco cybersecurity company HackerOne got serious about its written communications, its concerns went far beyond pesky split infinitives. For example, much of its messaging is aimed at hackers—not online criminals, but the kinds of ethical geeks who bristle at the use of the term “hacker” to describe the bad guys. To make sure it didn’t inadvertently tick off this critical audience through any sloppy phrasing or poor word choices, the company gave more than 50 employees their own writing coach: Grammarly. Famous—or maybe infamous—for its omnipresent YouTube ads, Grammarly has transcended the mandate implied by its name. Increasingly, the AI-infused service is helping companies fine-tune how their staffers write, expanding to “the style preferences that companies might have, the brand tones they prefer, the vocabulary they use,” says Grammarly CEO Brad Hoover. Thirteen years ago, Grammarly was a Kyiv-based fledgling that was known as Sentenceworks and expected students rather than corporate employees to be its primary audience. In 2010, when its Ukrainian cofounders Max Lytvyn, Alex Shevchenko, and Dmytro Lider met Hoover—at the time, a Grammarly fan who also happened to be a venture capitalist—they soon concluded that he should be the CEO, and they should focus on product, technology, and revenue. That led the startup to relocate its headquarters to San Francisco in 2012. (In the wake of Russia’s invasion of Ukraine, Grammarly, which says it still has “many” employees there, has committed $5 million in aid for the Ukrainian people.) A decade later, more than 30 million people and 30,000 teams use Grammarly’s free and paid versions. With a $200 million funding round last November, the company hit a valuation of $13 billion. CB Insights ranked it as the 10th most valuable U.S. startup; Pitchbook said it had become the most valuable natural-language AI company in the world, period. Grammarly’s booming fortunes reflect growing attention to the written word’s role in business. Companies, such as Amazon—where staffers must pitch new ideas in the form of six-page memos—and Stripe, have long been admired for their write-first cultures. But as the COVID-19 pandemic diverted a large chunk of collaboration from office chatter to text-based mediums, many more organizations have been taking a fresh look at how employees express themselves at the keyboard. “The importance of communications is clear, especially among knowledge workers,” says Hoover. “What’s been less clear, historically, is that there’s something that can be done at scale to address it.” Rapid advances in AI-based linguistic analysis have allowed Grammarly to fill that hole. In June 2021, the company upgraded its Grammarly Business offering with a raft of features designed to spread better writing throughout an organization, such as the ability to establish up to 50 style guides for use in different contexts, including customer support and social media. The service already had a tone detector that evaluated text on factors, such as level of formality and friendliness; now customers can define their own tones and have the service coach employees on achieving them. There’s also Grammarly for Developers, a new platform that enables programmers to embed the service in their products. Thanks to a deal with Samsung, for example, Grammarly writing suggestions are now built into the keyboards of Galaxy smartphones. As Grammarly gets more powerful and pervasive, one concern is whether it could grind the personal element out of writing in a way that’s counterproductive. Even today, Grammarly’s AI has gotten eerily good at making wholesale revisions to clunky sentences composed by humans; it isn’t hard to envision it taking on more responsibility for the collaboration, until it’s more ghostwriter than tutor. Startups such as Jasper—which uses AI to generate marketing copy—are already moving in that direction, with the user polishing text composed by a computer rather than vice versa. In its present form, Grammarly offers its advice gingerly and delineates its rationale clearly, which helps explain why even pro writers don’t see it as an imposition. “It’s enormously satisfying for me as a writer to kick its suggestions to the curb,” says Ann Handley, a digital marketer and author of Everybody Writes. “To say, ‘No, I don’t want to do it that way because this is in my voice, and this is how I’m communicating.’ ” Human Versus Machine: We ran an early draft of this very article through Grammarly. Here’s how we performed.

Grammarly stresses that it doesn’t want to wring the humanity out of language. “The way we communicate is part of who we are,” says Rahul Roy-Chowdhury, the company’s global head of product. “We embrace that richness, and we want to make sure that users are at the center of what we do.” For now, the company doesn’t have to confront all the implications of where its AI could take it. By encouraging millions of business professionals to craft more thoughtful prose, it’s accomplishing something new and significant. As HackerOne CMO Tim Matthews puts it, “Most people are okay with writing better if it’s easy.”

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