Photo courtesy of Grammarly
Shishir Mehrotra joined Grammarly as CEO following its December 2024 acquisition of Coda, the AI productivity platform he founded in 2014. The MIT graduate began his career by cofounding Centrata and subsequently spent several years at Microsoft and then at Google as chief product officer/chief technology officer for YouTube. MIT Sloan Management Review spoke with Mehrotra about navigating his unique leadership transition, building what he envisions as the AI platform of the future, and management rituals, which he’s writing a book about. What follows are edited highlights from that conversation.
MIT Sloan Management Review: What led to Grammarly’s acquisition of Coda and you taking on the CEO role?
Shishir Mehrotra: Grammarly is a much larger business than most people realize — it has over 40 million daily active users and over $700 million in revenue, largely bootstrapped and generating cash for a long time. People think Grammarly is mostly about grammar-checking. But actually, its core technology is the ability to bring AI agents right to your applications.
The Grammarly cofounders like to say it’s like they built a superhighway for AI agents, but there’s only one agent running on that highway right now — the one with your high school English grammar teacher. Meanwhile, at Coda, we had built hundreds of agents that connect to other systems.
The thought was, what if we put these together into a single platform? When you’re writing a customer memo, not only can Grammarly tell you about grammar issues; it can also have your sales agent telling you the latest update for that customer, your product road map agent helping you fill in feature information, and your support agent informing you when this customer last had an issue — all in the applications you’re already using.
Taking on the CEO role in this way is a unique opportunity. It is unusual to simultaneously go through an M&A transaction while onboarding as CEO of the overall entity. We get to take the best parts of both products and put them together, but also the best parts of both cultures.
I’ve been following an eight-week onboarding process that I’ve used for new executives for years. The early weeks are focused on learning and observing, which in this case happened bidirectionally, with each management team learning about the other. Then you set your plan and start pushing forward.
Grammarly has been around since 2009, but the competitive landscape for AI has changed ever since large language models arrived on the scene. What is Grammarly’s role in the future of AI?
Mehrotra: It is my goal for Grammarly to be one of the top three or four AI companies in the world, and I think that’s quite possible.
Obviously, there are great players building foundation models for everyone to use. But most services in the application layer have built closed walled gardens — the Microsofts and Googles of the world are focused on making their own products work well together. Our unique opportunity is bringing an approach that delivers agents to users wherever they are. Changing where users work is very difficult, but giving them assistance where they already are can be incredibly powerful.
What prompted you to write a book about management rituals?
Mehrotra: I’m working on the book in public at ritualsofgreatteams.com. The idea came from a conversation with Bing Gordon, former chief creative officer at Electronic Arts, who observed that great companies all have “golden” rituals that are named, templated, and known by every employee by their first Friday. Amazon does six-pagers, Google does OKRs [objectives and key results], Salesforce does V2MOM [vision, value, methods, obstacles, and measures]. His conjecture is that if you want to be a great company, you need to build your own set of golden rituals.
I got excited about this idea, and I’ve now interviewed about a thousand leaders to collect and categorize the best 100 or so rituals. One of my favorite perspectives comes from Dharmesh Shah, founder of HubSpot. He pointed out that as company leaders, we actually build two products — one for our customers and another for our employees. That second product we call culture, which manifests as rituals.