RAHUL ROY-CHOWDHURY: When I was in college, I was a math major, and I was interested to understand how we could develop a model of the world to start inferring facts and knowledge. I came across Alan Turing and a future he had imagined on intelligent machines. Alan Turing’s work, this theoretical construct of what computation actually is and what it enables, was, I thought, just a deeply compelling and deeply creative piece of work.

JEFF BERMAN: Long before Rahul Roy-Chowdhury was the CEO of Grammarly, he was a PhD student obsessed with Alan Turing — considered a founding parent of computing — and Turing’s ideas about what we now call artificial intelligence. But Rahul wasn’t content to sit around studying for very long.

ROY-CHOWDHURY: I published a paper in a pretty prestigious AI journal. It was kind of a big deal that I had this paper published pretty early on in my PhD career. But I felt that I wanted to have a bigger real-world impact. I was wondering how many people even read this paper. This is not a value judgment in any way, but I felt like I needed the real-world impact of the work that I did to really feel motivated to do that work. So I realized that maybe academics wasn’t my path, dropped out, joined industry, and here I am decades later.

Introducing Rahul Roy-Chowdhury & Grammarly

BERMAN: Rahul spent most of his career leading technical teams on ambitious projects, like building the Chrome browser at Google. In 2021, he joined Grammarly as its Head of Product. Soon after, he took over as CEO. 

Rahul is tasked with steering the 13 billion-dollar company through a chapter of profound disruption. For most of its 15-year history, Grammarly’s writing assistant software has been a market leader. 

But new competitors are crowding the field. Tools powered by large language models like ChatGPT, Inflection’s Pi, and Microsoft’s Co-pilot now offer to improve your writing, too – sometimes for free. 

I talked with Rahul about how Grammarly is handling the threats — and opportunities — that come from the latest AI advances. 

BERMAN: I’m Jeff Berman, your host. 

Before we jump in, just a note that Grammarly is a paid sponsor of Masters of Scale. Our chat with Rahul was planned, recorded, and edited separate from that relationship. 

Rahul, welcome to Masters of Scale.

ROY-CHOWDHURY: It’s great to be here. Thanks for having me, Jeff.

BERMAN: It’s great to have you here. I was tempted to ask Grammarly to help me with my opening question for you, but it’s a simple question. So, for those who haven’t worked with Grammarly, how do you describe what Grammarly is and what you do?

ROY-CHOWDHURY: Yeah, this is something Grammarly could have helped you with if you had asked, but the mission of Grammarly is to improve lives by improving communication. We’re here to help people communicate better, to communicate more effectively, to get your point across, to be understood.

BERMAN: Why do you think that’s so important, particularly now, as we sit here talking in 2024? Why is clear and effective communication important enough to be the core mission of a company?

ROY-CHOWDHURY: Well, communication has always been important. If you want to go way back, it’s what defines us as a species. We’re a social species. We communicate with each other, and our success depends on how well we can collaborate and make our intentions understood to a large group of people. What’s made it particularly important is a couple of things. One is I can actually use software to help me in doing this important task. But then over the last couple of years, teams have become more distributed and more global. And through the pandemic, it accelerated what had already been something that is in progress, which is more remote work and more sort of distributed teams communicating increasingly asynchronously. And so as a result of all these changes, the weight of the written word was more than it had been in the past. And so the importance of using a tool like Grammarly to make sure that those written words are impactful and have the desired effects is more important now than it has been ever before.

BERMAN: I’m curious, when you came in to take the CEO role at Grammarly, was there something from your personal life or your own work life that really animated this as a mission for you personally?

ROY-CHOWDHURY: The thing that animates me and defines the choices I’ve made in my career are I’m a tech optimist, and I want to work on the hardest, most impactful, most meaningful problems that technology can solve. So way back when, in the early days of my tenure at Google, there was a project to build a better web browser. It was called Chrome when I joined Chrome, success was far from assured. It was this mission of improving the web platform. And I love that mission. I love the idea that we could create a platform that anyone anywhere in the world could access. It was an incredibly rewarding journey a decade in. Fast forward to 2021, I came across Grammarly, and I had that same feeling that I did in the early days of the Chrome browser and the web platform. And I felt like, you know, communicating well is such a hard but such an important problem to solve, and if technology can help you do it better, what a great mission to sign up for.

The speed in which AI is evolving

BERMAN: About 18 months after Rahul joined Grammarly as Head of Product, the Large Language Model revolution took hold. 

Open AI released ChatGPT for public use in November of 2022. That opened the floodgates for AI-assisted … well, pretty much everything. 

Grammarly knew it needed to adapt — and quickly — to this technological shift. So Rahul was asked to take on the role of CEO, just a couple of years into his tenure. 

Two of three co-founders are still heavily involved with the company. 

With their support, and his background in building tech products, Rahul is well-positioned to lead. But the job can still be daunting.

ROY-CHOWDHURY: AI is not for the faint of heart. The pace of change in AI is unlike anything I have seen before. I’ve been thinking about AI for a while. Way back when, in fact, I was in a PhD program in AI. I dropped out. I didn’t finish. But it’s been on my mind.

And I’ve never seen the level and speed at which the technology is evolving, and the capabilities are evolving and getting better. That’s a wonderful thing. I’m a tech optimist, and I think this is going to make all of our lives incredibly strong, powerful, successful. It’s going to be this big way to augment what we do every single day.

And, there’s ambiguity and uncertainty in the road ahead because the pace of change is so fast, but my experience is working on meaningful things, is hard and ambiguous, and that’s what makes it meaningful and worthwhile to pursue .

Reimagining the future of Grammarly

BERMAN: We’ve done a number of Masters of Scale episodes with successor CEOs. Some of them are what are often referred to as refounders. They’re tasked with really almost reimagining the company for this next phase or actually doing so as opposed to continuing on its current path or slightly evolving it. Do you think of yourself more as a refounder or more as an evolutionary CEO of the company?

ROY-CHOWDHURY: You know, I’m not sure that either of those really neatly fit the place we’re in.

BERMAN: How would you describe it? 

ROY-CHOWDHURY: What I describe is, for example, we have a longstanding investment in user trust, privacy, security. We’ve really invested deeply in this area and those investments are going to be paying massive dividends because user trust is a core value, but even more important now in the age of LLMs. All this data, what’s happening to the data, is my data safe? What’s the motivation of this company that’s collecting my data? We’ve also been extremely focused on making sure that we are bringing technology to bear to solve real user problems. Seems like an obvious thing to say, but often you can end up getting enamored of the tech and lose sight of actually how it’s going to help a user. And so we want to keep all the things that have made Grammarly what it is today. And then re-imagine how we can think about increasing the value we provide to users in the age of AI. So it’s not a refounding. It’s not an evolution. It is taking what makes the company great and special and set our sights to the future. 

Facing a new wave of competition

BERMAN: Grammarly has been at this for 15 years. You’re the market leader. You can’t listen to a podcast or put on a sporting event without hearing or seeing a Grammarly ad. But you’re facing a new wave of competition that is rising about as rapidly as scaled competition has ever risen in any industry. So how do you think about that competition and maintaining your market position?

ROY-CHOWDHURY: I welcome it. I’m a firm believer that we want to stay focused on solving real user problems. That’s always the foundation of everything we do. I don’t want to spend a lot of my time looking over my shoulder at what other people are doing, because that’s time taken away from: how can I uniquely provide a solution to that user problem? You can think of a simple view of the life cycle of communication being there’s a conception phase, there’s a composition phase, there’s a revision phase, and there’s a comprehension phase at the other end. And so, we have historically focused on primarily the revision phase of this life cycle. Not because we wanted to but because the technology didn’t really enable us to help people along the full spectrum of this communication journey. Now with large language models, we can. We believe Grammarly can really reimagine how we communicate across all these different tools.

I’m sending you an email, and maybe I want to include some context from a project update. I just had a conversation about that project update in a different channel maybe in Salesforce or maybe in Slack. Now Grammarly is in all of these different forums. And so maybe we can pull in the right context at the right time to help you do your job better. I think we can be more effective at work. And I think we can remove some of the drudgery and make work more fun. I’m sure we’re not the only people who have seen this opportunity, hence competition. But that’s great. That’s how a free market works, and I think that’s good for consumers.

BERMAN: Have there been specific customer stories that have really motivated you or helped shape your product roadmap?

ROY-CHOWDHURY: There’s a specific person I wanna call out here. His name is Mark Francis Long. He’s dyslexic and actually has a dyslexia advocacy group called I Am Lex. And he has talked really movingly about how Grammarly has helped him navigate his professional life. 

He sees Grammarly as a tool that is looking over his shoulder, helping him correct and remove all the inaccuracies in his communication that he felt were holding him back. And so he has this very inspiring vision of I Am Lex, which is there’s a superpower in dyslexics seeing things and pattern matching differently.

And so how do you harness that superpower, but get the help you need? And that’s the role that Grammarly plays. And he has a TED Talk. It’s wonderful. I highly encourage everyone to see it. But that’s one of those inspiring stories. And we have dozens of those every single week. It’s what motivates me to come to work every day.

Educating schools about using AI

BERMAN: I love that. And I mean, you know, the legion of dyslexic business leaders and political leaders: Richard Branson, Charles Schwab, Governor Gavin Newsom in California, who have that superpower, but also have had to work really hard to overcome the learning challenges. These new AI tools, including Grammarly, are just such a massive unlock for so many millions of people around the world who have those learning challenges. 

Two of my kids are dyslexic, and so, you know, tools like Grammarly are lifesavers. My kids are better students. They become better writers. And yet they go to a school, which is a wonderful school.  But that, at least for this past year, banned the use of AI tools, beyond effectively Google spell check because of concerns about, you know, cheating and where the lines are, and I have a lot of empathy for the school administrators. 

And yet I’m looking at this going, this is insane. These are the tools of the next decade plus. They need to know how to use them. They need to be literate in them. So given Grammarly’s leadership position in the market, how do you think about educating not just companies, but schools about these tools and how to responsibly deploy them?

ROY-CHOWDHURY: Yeah, we are in active conversations with literally hundreds, maybe thousands of universities across the U.S., across the world, all grappling with this question of this big technical shift. 

“I’m afraid of it, on the one hand, but I see the potential of it, on the other hand. And also, I feel some pressure to make sure my students graduating from my institute of higher learning are prepared for the jobs that are going to be created in the future, based on AI.”

 So, we, first of all, want to have a constructive dialogue. I understand the concern and the fear. It is very new. It is moving very, very quickly as well. And so, we talk to educators on a regular basis. We learn from educators on how we could improve the product or change the product in ways that ease some of those concerns. And also just educating folks on this technology is not something to be feared. It’s something to be embraced. And if pedagogical mechanisms need to evolve to take account of this new technology, that’s great. As an example, one of the features we added to our product for education specifically, which I love, is you can use generative AI in Grammarly, and maybe you’re writing an essay or doing some other piece of work product for your college, and then Grammarly at the end can offer to cite your use of AI. So what are the prompts you ask Grammarly for? How did you actually use AI? And so if the only prompt was: give me a 500-word essay on the Civil War, you didn’t engage in the material. I can see that. But if someone’s prompt was, help me strengthen my second paragraph on this point, give me a critique on whether I’m actually persuasively using data to make this point. And then you can see that this interaction with AI helped someone engage more deeply in the material and created a stronger work product at the end of it. So, I think these are all solvable problems. We’re engaged in these conversations every single day and we want to be part of the solution.

BERMAN: Still ahead, I talk with Rahul about how he thinks AI will shape the future of work. 

[AD BREAK]

BERMAN: Welcome Back to Masters of Scale. You can find this full interview and more on the Masters of Scale YouTube channel.

Building trust amongst customers

You referenced trust in our conversation, and I’m struck by the framework that you’ve developed that goes by the acronym TRUE: trust, responsibility, user control, and empathy. Can you talk about how that framework came into use and, and how you actually employ it at Grammarly?

ROY-CHOWDHURY: You know, it reflects our existing practices. It was just honestly a reflection of what we already did. It was a helpful way to frame all the things we were doing, to evolve our product, but do it in a way that was true to our values. So for example, trust is critical. And I think we created the true framework.

It was pre-LLM scaling, but it’s more true now than ever before. So all of our investments in a multilayered security program, all of our investments in privacy and user control, all of those things are critically important now, in fact, more important now than ever before. So, it helps us to have a north star in terms of what the key capabilities are and the key values that we want to keep in place because it’s a very fast-moving landscape, and you need some framework to make decisions.

So the TRUE framework is our framework to make those decisions. So as an example, there’s an open question with AI in terms of, well, “is this data going to be used to train the model?” or “how do I think about my data?” And because trust is a key pillar of how we approach our work and because that’s been true from day one, we have the opportunity for every single user of Grammarly, free or paid, individual or business, to opt-out of using their data to train Grammarly’s models. So that user-control is part of what we mean by trust. So there’s meat behind each of these things. It’s not an empty framework, but something we use in practice every single day to make decisions.

How to deploy AI ethically

BERMAN: You alluded to this earlier. One of our co-founders, Jai Punjabi, says all the time how this is the worst the AI will ever be, right? Every day is literally the worst that will ever be. It’s getting better by the day. And at the same time, it’s not only not linear, but there are dips, right?

So, we’ve seen, for example, AI agents return results about how to keep cheese on pizza by using glue. Because that was in a Reddit post that made its way into the data set that the LLM was trained on. So, I’m curious when you look at what’s happening in the industry. There’s a halo effect when everyone’s employing a true model.

There’s almost a devil effect, when they don’t. And the media obviously loves to latch onto these stories. So no matter how much of a tech optimist you are, these stories really deeply undermine trust in AI. So, I appreciate that Grammarly is doing this. As you, as an industry leader, look across the landscape, how do we make sure that more AI companies are employing these, these core principles so that we grow in the right way?

ROY-CHOWDHURY: I think we as an industry need to take our responsibility to deploy powerful AI systems very, very seriously. This is a very profound shift in how we do our work. The scale of the shift, like all big platform shifts, I think it’s a bit overhyped in the short term, and it’s underhyped in the long term.

And so we, as purveyors of this technology, need to really understand what this means — how people will do their work, what it means to knowledge work in general, and the impact it has on knowledge workers. And we’ve got to take that responsibility very seriously. What’s unhelpful in these conversations is very abstract arguments about existential risks posed by A.I. These are tools that we can use to augment our potential. That should be the conversation. It’s actually quite prosaic. The set of issues that you need to think about are quite prosaic.

How good is the quality of the training data? What specific investments are you making to make sure the training data is high quality? It’s been annotated well, it’s been quality checked? How are you evaluating the output of the model? How are you building classifiers to understand sensitive text and take corrective action?

We have built, for example, a sensitive text classifier. It’s a project that we called SeismoGraph, and we’ve open-sourced it. 

So imagine you’re getting a bunch of text, maybe someone has written the text or maybe it’s output from an LLM, and the text may be sensitive. Maybe it’s got hate speech, or it’s got some other sort of issues.

And so we built this classifier called Seismograph that does that sensitive text detection. And so as an application, you can look at that output and say, it looks like this text is sensitive. I can now take some corrective action.

I can suppress that, so the user never sees it. Or I can go back to the LLM and say, “That text wasn’t great. Give me another version.” So we built this. We found it very useful for our users to keep them safe. And because we want to contribute back to the open source community, we open source seismographs to anyone who is facing an issue of sensitive text.

So we hope that other people in the community can take the work we have done and deploy it in their own AI applications. And so I think we can share best practices because as an industry we must make sure that this technology is deployed in a way that augments human potential.

“I would like to bet on open source as the future of AI”

BERMAN: How much is open source part of your next phase of scaling in your vision of this?

Open source is going to be critical. So first of all, as Grammarly, today, we are doing a bit of open source, a bit of closed source. We have a set of different models we’re using, but long term, I would like to bet on open source as a future of AI. Now, setting aside Grammarly, I think just as an industry, given the power of the impact that AI can have on how we do our work, I think the sunlight that open source brings is something that we as a society, as an industry, absolutely should be pushing for.

BERMAN: Where does your belief in open source come from? How did that originate?

ROY-CHOWDHURY: I’ve just seen it. If you look at Windows and Linux, all of these data centers that are powering compute, they’re all based on Linux. If Windows had won the Windows versus Linux battle, the world would have looked very different, and I think would have been less able to scale and take advantage of this new AI desire for compute. I see this with open-source web products. This is my first-hand knowledge. But in general, I think there’s a lot of fear that gets created because transparency is scary. But ultimately, that provides us the best way to harden our systems because every tool can be used for good or evil, tools themselves are immoral, transparency is the surest way that I’ve seen in the history of tech to really harden those tools.

Will AI create — or take away — jobs?

BERMAN: Yeah, and yet, you can also, I’m sure, appreciate that particularly for people who are not working in this day in, day out, headlines are scary, and there’s a lot of science fiction, which was seemingly decades off, which is now, it’s manifesting in reality today. And one of those concerns is job displacement.

I know you, unfortunately, went through a reduction in force recently, had a round of layoffs as you prepare for this next era. How do you think about balancing your responsibilities to your team with building the best run smartest company possible and making sure that AI is a net job creator, and we don’t fulfill some of these more dystopian visions of what AI can do?

ROY-CHOWDHURY: I think, first of all, I do think that AI will be a net job creator. You know, back in the day when ATMs were first getting widely deployed in the U.S., there was a lot of fear that bank teller jobs would be extinct, a thing of the past. But the reality is what happened was ATMs allowed bank branches to be created at a much lower cost.

Therefore, there were many more bank branches, and therefore the need for tellers only increased, and tellers could then focus on higher value-added tasks instead of routine transactions. I think this is a pattern that we see over and over again with new technologies, and I think AI is exactly the same. There will be some displacement. And so some types of jobs will need to be reimagined and rethought, and I see that as an opportunity. I would encourage all of us, and we in the tech industry need to do our part to make sure people understand how they can harness AI to do their jobs better, more effectively, and really augment their skills that they have.

You know, there’s this thing that people say, which is, it’s not that AI is gonna take your job, it’s that the person who knows how to use AI will take the job from someone who doesn’t know how to use AI. I do think that is true, and it is a bit of a sobering thought, and so I do think it’s important for all of us to embrace the opportunity and understand how we can harness the power of AI.

Because, remember, we’re not passive observers. We control our destiny. We decide how AI can be used to help us be better, do better, be more effective. And so I would encourage all of us to just seize that. Be active actors in the story of AI.

Pulling out of Russia after the Ukraine invasion

BERMAN: Grammarly’s been a leader on not operating in countries where values misalign. So you all are one of the countries that pulled out of Russia. After the invasion of Ukraine, the war in Ukraine, I’m curious how that specific decision was made?

And then more broadly how you make decisions about, you know, when to say we’re taking a public stance here because it’s the right thing to do or the world needs us to do it or what have you?

ROY-CHOWDHURY: Ukraine is a very core part of Grammarly. Our founders are Ukrainian. We have a big presence in Kyiv. We have many of our team that is based in Ukraine, still to this day, is based in Ukraine. And when the war broke out, it was a shock. It was a shock to all of us. And particularly a shock to all of our team members in Ukraine. And so to me, this is a very simple decision to make.

This was really about showing our team in Ukraine that we were behind them 100%. And so we canceled Grammarly availability in Russia and Belarus because there’s active military operations against people that we knew who are colleagues of ours in harm’s way. So that was an easy decision for us to make.

I don’t think it’s reasonable for us to have a position on every single issue that we’re facing as a society. Why would anyone want to know what Grammarly thinks about some, uh, some topic?

Where we feel that there’s a very clear values alignment for us to take a stand, we will absolutely do it. But I also don’t want to virtue signal by having opinions on everything.

The future of work & Grammarly

BERMAN:  What’s the question I haven’t asked you that you wish I had asked you?

ROY-CHOWDHURY: The question, I think, is how does an AI-enabled future of work — what does that look like? How does that manifest?

BERMAN: So let me ask you, what does an AI-enabled future of work look like? How does that manifest?

ROY-CHOWDHURY: Yeah, great question.

BERMAN: I got it from a great source.

ROY-CHOWDHURY: So, today we spend most of our time having conversations with other people at work, as I mentioned, communicating all these different settings, all these different forums, across all these different applications. And we are consuming a ton of information as well. And so I don’t know about you, but certainly, I feel like I’m always on the edge of keeping up with all the things I need to keep up with. I’ve got all these Slack messages, I’ve got all these messages, emails, documents that I’ve got to read, I can barely keep up. 

Now people are saying, “All right, well, we’ve got AI, and it’s going to be great because we can now create content at very low cost.” So the issue is, if you drop the cost of content creation down to zero or near zero, you’re going to get a lot more content. Simple law of supply and demand. How does that manifest into a better future? Because I’m already struggling with all the content I have to consume. So how does having more content help me? Who’s going to read all that content? And so the better future driven by AI has got to rethink how we do our work and how we go about our day-to-day lives. And so the vision we have for Grammarly is that we reimagine your workflows, we reimagine how you synthesize information, get insights from your information to do your work better, make it more fun, make it more focused on higher level thinking versus drudgery, and that’s what the future will look like.

BERMAN: And is part of that, Grammarly becoming increasingly more relational? So that it really understands the nuance of how I write and speak my, my culture, my nationality, my background, my personal quirks is part of it really, making sure that we’re not consolidating everything to fit one form, but actually we’re giving everyone the ability to do the best version of themselves as communicators?

ROY-CHOWDHURY: Yeah, absolutely. A couple of ways I think about the role of technology and the role of Grammarly in evolving AI tools in general. First is, for me, writing is thinking. And so I never want to outsource my thinking. And therefore, I don’t want to outsource my writing. So I want to use Grammarly as a tool, as a companion, but not to replace my own critical thinking. And second, the way I sound is so much a part of who I am as a person. And that’s true for everyone. The way we sound defines who we are as human beings, the way we communicate. And so the role of a tool like Grammarly is not to replace that with some sort of a lowest count denominator or robotic sounding or generic sounding output, but to keep true to your voice. To make sure that you are in control of the experience, that you have agency in the experience, that you’re not outsourcing your thinking. And use Grammarly as an aid, as a tool that gives you superpowers to show up better, that’s a role that we wanna play in this AI-enabled workplace of the future. 

BERMAN: Well, this has been a terrific conversation. Thank you for being a guest on Masters of Scale.

ROY-CHOWDHURY: Thank you for having me. It has been wonderful to spend this time together.

BERMAN: Grammarly is facing an unprecedented onslaught of competition thanks to new AI tools. And Rahul is eagerly deploying artificial intelligence to improve Grammarly’s products. 

But his approach to this challenge is also steeped in the company’s values. 

He is planting a flag when it comes to earning — and keeping — the trust of Grammarly’s customers. 

Rahul is optimistic that this combination of innovation and commitment to values will be a winning combination. It may be a useful business approach for others navigating the AI arms race — we know it’s an essential approach to keep us moving down the path of the more utopian vision of an AI-assisted future.

I’m Jeff Berman, thanks for listening.