A couple years ago, many people thought ChatGPT would be a threat to Grammarly. Instead, Grammarly is not only thriving today, it is being reimagined for the agentic era. In this episode of Creative Intelligence, Grammarly’s new CEO, Shishir Mehrotra, shares a radically different vision: Grammarly isn’t a grammar checker. It’s an AI superhighway. And grammar was just the first car.
Since joining Grammarly after its acquisition of his previous company Coda, Shishir has been reshaping the company's vision—and, more broadly, rethinking the future of productivity tools, agents, and work itself.
This conversation was full of insightful analogies and practical frameworks for business leaders. Below, I share some themes that stuck with me but let me first advocate you really need to listen to the whole episode. Shishir is someone whose clear thinking I have always admired and in this episode he covered a lot of ground: the future of workplace productivity, how to transform companies around AI, setting bold AI visions, and how a leader should think about company culture.
Imagine you show up to your first job and already have a team of 50 direct reports. They’re not people but AI agents. They work 24/7, don’t argue, and know everything in your knowledge base. Shishir thinks it’s where we’re headed.
“Imagine you showed for your first job and you had a team of 50 that worked for you … and your job is to lead this group. The skill that humans are going to need more of is management … Every employee starts off managing a team of agents. That’s the new baseline.”
(Timestamp: ~18:00)
I like this thought because it reframes the question from “Will AI replace me?” to “How do I orchestrate and lead this new team I’ve just inherited?”
Grammarly is misunderstood by many including me. What people see is grammar suggestions. Shishir argues that what’s actually under the hood is a distributed AI agent framework that operates invisibly across thousands of apps, from Google Docs to Apple Notes to Slack.
“Think of Grammarly as the AI superhighway. So far, only one car has been on it—your high school English teacher. But now we’re opening up the road to all kinds of agents.”
(Timestamp: ~4:00–12:00)
This shift in framing offers a glimpse of what AI-native software might actually look like. But it also offers a framework for how to reinvent companies around AI (Timestamp ~ 34:00). We covered several enablers of this business transformation ranging from how to manage employee mindset to platform choices and company culture.
Shishir has a forthcoming book on team rituals and we spent some time talking about it. He explains an idea he first heard from Dharmesh Shah of Hubspot: a company doesn’t just build one product. It builds two: one for customers, and one for employees. And culture is that second product. Shishir goes on to say that company rituals are how you put them in practice.
“If values are what you believe, rituals are how you behave.”
(Timestamp: ~38:00-46:00)
He shares a standout example from Coda and Grammarly: a ritual called Dory (ranked Q&A so everyone can equally influence the agenda of team meetings) and Pulse (removing groupthink so you get everyone’s inputs. It’s worth asking what rituals you are using in your company and why.
The conversation shows how a company that could have been “disrupted” by AI chose instead to reimagine itself around it—not just defensively, but with a bold, forward-looking vision. That’s something many leaders can learn from. Overall, there is a lot to take away and implement here.
Finally, a preview of the next episode: I had a great conversation with several AI leaders at the recently concluded Wharton Global Forum. My next episode will be based on that live conversation and will explore a range of themes from AI-centric product strategies to measuring RoI from AI investments.
0:00 Introduction – Why ChatGPT Didn’t Kill Grammarly
7:00 The AI Superhighway: Why Grammar Was Just the First Car
13:30 Agents and Productivity;
18:00 Why Everyone Will Be Managers (of Agents)
22:00 Which AI tools to use today?
32:00 Reimagining Education
34:30 Playbook For Business Transformation Around AI
38: 30 Building culture with rituals
46:00 Rapid-Fire Productivity Confessions
50:00 Final Reflections
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