Grammarly acquires Superhuman to build an AI-native productivity suite—and is planning a rebrand

Jul 7, 2025 · Full transcript · This transcript is auto-generated and may contain errors.

Featuring Shishir Mehrotra & Rahul Vohra

persist indefinitely into the future. Um unless and until some sort of technology could reduce the severity of severe weather. Um we went through this with the California fires.

You know, it was like everyone was searching for like a single person to pin it on and like it came down to like, you know, some people built their houses the wrong way and there's some building codes that need to change and there's some water rights and water flow and there's some different like we need more goats in certain areas.

There's like a million different things that could have prevented this if they all were all working together as a welloiled machine and had the forethought. Um, but it's a very very frustrating and difficult situation. So, our our thoughts and prayers are with everyone who's been affected.

Um, but thank you so much for stopping by. This is fantastic. Thanks for uh breaking it all down for us. Thanks, guys. Appreciate it. Cheers. Really quickly before our next guest joins, let me tell you about Linear.

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I use it personally. Um, and we have our next guests. We're doing two guests simultaneously. I hope production team was made aware of this. It's on the calendar. Um, but we are working to get a a four up display for you. Uh, we have uh the founders of Grammarly and Superhum.

This was an acquisition that was ex that was announced last week and lots of people in tech have probably used Superhum. It's the email client of choice for the tech elite, of course, and Grammarly. Has been an indispensable tool at TVPN.

We installed it on our producer Ben's computer very early on when we were posting clips to make sure that we didn't have any uh spelling or grammar errors when we would post on social media. Very useful tool. And now they've combined forces.

and we're going to talk about how we can uh what the shape of the business will be going forward, how these products play together, what the modern suite of tools looks like going forward. Well, welcome to the stream. How are you? Great. How are you? Fantastic.

Uh would you both mind kicking us off with an introduction on yourself and uh the companies that you run and then we'll talk about the the the acquisition? Great. Uh sure, Mah, you want to go first? Okay. Yeah, happy to. Uh, hello everyone. I'm Rahul Vora.

I'm the founder and CEO of Superhum, which if you're not familiar with is the most productive email app ever made. Imagine getting through your email twice as fast as before, responding faster to the things that matter, and saving 4 hours or more every single week.

We're also inventing the future of productivity with AI. Imagine waking up to an inbox where every email already has a draft reply. You would simply edit and then send. And of course with Gramly we are going to build the AI native productivity suite of the future. Great. Amazing. Yeah. I'm Shashir Motra.

Um I actually started a different company. I started a company called Kod um about the same time as Rahul started superhuman and about uh 7 months ago or so um Grammarly acquired uh KOD and I stepped into the CEO role running uh Grammarly. So been working in and around the industry for a long time before KOD.

I used to run the YouTube group at uh Google, worked at Microsoft in the early days. Actually started my very first job was working on Outlook. So I've got back in 1998. I worked on email or email. Fun to come back to it. Yeah, that's amazing.

Um so I I'm not sure who's best to answer this, but I'd love to know about uh how this deal came together. um when you two first met and uh you know we we we keep going back to this post that like you'll meet your acquirer like five years before you uh before the deal goes through. Is that this case?

Is this a narrative violation? Uh kind of how do you get to know each other? Eight years. Break it down. Why don't why don't I take the first half and then Rahul can take the the second half. Um so I can talk a little bit about the deal and what we're doing. Um and Rahul can give the fun origin story.

Um so um maybe just as a as a little backgrounder for everyone. So, Grammarly at Grammarly, our goal is to build an AI native productivity suite with the agents and applications that drive productivity for every individual and team in the world.

Um, so a lot of that is probably new to people because people have generally thought about Grammarly as a much narrower product uh than our aspirations for it.

And you know, the way we generally talk about it and I'll talk about agents first and we can talk about applications, but we generally think about Grammarly as the OG agent.

It's uh about uh 16 years now um that the company has been helping at this point about 40 million daily active users where Grammarly is the communication assistant that lives right next to you in every surface you work in.

But people misunderstand the technology because they think it's about grammar but actually the technology of Grammarly is mostly about bringing AI right to where users work. So we can work in about 500,000 different applications where we read what's on your screen.

We can annotate it in an unobtrusive way and we can make changes on your behalf. And so from that perspective, we we call this layer, we call it the AI superighway, bringing AI right to where people work. And in that analogy, up till now, we've only been running one car on that highway.

That's the car with your high school grammar teacher in it. And that's a very useful car. and it generates, you know, over 800 uh 78 $800 million in revenue now. But I think it's a uh a vast subset of what you should be able to do with that.

And so a big part of our strategy is opening up Grammarly to become a platform so you can build any sort of agent on it uh and have those agents come to you where you work. That's the first part of our strategy.

Second part of our strategy is taking those surfaces and building the first party versions of the surfaces that we think really matter. the surfaces where people work um every minute of every day where all the work really gets done where you really want to work not not only alongside humans but alongside agents as well.

So that's why we bought my prior company KOD that we make an all-in-one document solution that blends documents, spreadsheets, presentations, applications into one surface that produces all the work artifacts for you. But another key part of work is communication.

And for many people the dominant communication tool they use is email. um uh it's something like 3 to four hours a day the average person spends in their email inboxes and this actually shows up in the Grammarly stats really high. So email turns out to be the number one use case of Grammarly.

Um we uh revised something like 50 million emails per week. Uh it's three of the top 10 applications that Grammarly is used in are uh our email clients. Um and so we saw that as an obvious place to go to go work next. Now from my perspective I think email is a category that is particularly ripe for disruption.

As I mentioned I started my career working on Outlook in 1998. Um and since then there's a round of innovation with Outlook. There's a round of innovation with Gmail and then there was a decade of not much and then Rahul came along and built a great email experience.

So when we went looking for which surfaces really matter, we landed on email. And when you look at the email category, as you mentioned, there's only really one player that's meaningfully innovated in that space. And that's when we call Russ. That's a little bit about how the deal came together. Amazing. Great.

It's funny. I I just just for some added context, I basically have been lucky that my entire uh I think I got on Superhum in 2018. You launched in was it when did the beta launch? It was 2017. Our first paying customers were at the very end of 2017. So you're Exactly. Exactly. But I graduated college in 2018.

So as a professional, I've only had to experience I'm a lucky I'm the lucky batch, right? Um and uh still use it today. Um so so thank you for uh you know make I I never had to be an Outlook guy. I had a yahoo. com email address when I was a kid. Yeah. Vintage. Vintage.

Um, anyways, uh, Ra Rahul, I don't know if you have anything to add, but then I have a bunch of kind of follow-up questions on on the last anecdote. Yeah, for sure.

I think it'd be fun to tell the the origin story of the deal, how it came together, and I think there's a lesson or two in here for for other founders or the entrepreneurs listening. So, I'll also try and make it useful. Uh, so to your point, the foundations, the the seed for this deal was planted many many years ago.

It was 8 years ago, like said, it was back in 2017. And back then he was the co-founder and CEO of a company called Koda. And we were actually at a conference together uh in Hawaii. So it was really nice. And uh that said, I didn't really want to go.

You know, this was a four or five day thing accounting for travel there and travel back. And one of my co-founders, VC Soda, was really encouraging me to go.

you know, he he would say things like, "Listen, building a startup is just as much about who you know and the connections that you have and being able to pull opportunities together as it is building and marketing a great product. " And I'd be like, "Well, I, you know, I want to work on this feature.

I want to do this thing. " But in the end, he just pushed me out of the office and put me on a plane and go to Hawaii to Hawaii, which sounds weird, right? Like resisting going to Hawaii. But anyway, there I was. Uh, Shashir was there as well. And it was one of those special moments where nobody else was around.

So, it was just the two of us by a pool, two productivity nerds nerding out about productivity. And he told me that he'd worked on Outlook back in the day. We got into some really deep conversation about productivity. And as you know, back then we only did one-on-one VIP concage on boardings.

You must have gone through one yourself if you on boarded in 2017. Uh, so I on boarded him right there and then, right by the pool. And those who've gone through the onboardings know one of the very last steps is when we ask you to close Gmail.

And so I was asking him to move the mouse over to the Gmail tab and close it. And when I asked him to do that, another tab caught my eye, which was an app called Krypton. So I asked him, "What is that thing? " And then Shashir then proceeded to give me the best product demo I had seen in years. My jaw hit the floor.

It was a document, but it was also a spreadsheet. It was also a database. It was a collaboration tool.

was a mini app builder and and maybe today we take these things for granted but back then in 2017 this was truly mind-blowing and so Krypton then renamed to become coder and coder of course late last year joined Grammarly now in his acquisition announcement he wrote and I have the quote here as I watched the foundational capabilities of AI change how just about how every tool and surface operates I started drafting my 2025 memo for the team I titled it the AI I native productivity suite.

And this just set a whole bunch of bells off in my brain in a good way because at superhuman our vision has always been to build the AI native productivity suite of choice. And email is obviously a critical part of that. It's a much bigger problem than most people realize.

There's roughly a billion professionals in the world and on average we spend 3 to four hours a day in email. So that's 3 billion hours every single day or north of a trillion hours every single year. we actually all spend more time in emails still than any other work app.

So we caught up uh early this year in January actually a few days after he became the CEO of uh Grammarly and over the course of several conversations it became very clear that we were working towards the same vision which is to build this AI native suite for apps and agents and and then as Shash said email sits at the heart of where Grammarly is used today.

It's the number one use case helps write more than 50 million emails. Another stat that I found very fascinating is that 17% of words accepted on Grammarly are actually accepted in an email service. Wow. Okay. Bunch bunch of questions. Uh and I'm sure I'm I'm excited to get your answers. So, first is integration.

H how do you see sort of the the the plat, you know, how do you see both the brands and the products integrating and working together over time?

because you have a great challenge of having three great products that people love and three brands and uh in order to deliver on this this you know uh this true you know long-term vision of a of a productivity suite I imagine over time you want to integrate them deeply um I'm curious what that looks like yeah maybe you want to cover the product part and I can talk about the brand part sure yeah I'll I'll do product uh really briefly and then we can go as deep as you You know, I think one of the most exciting things about the deal from a superhuman perspective is the access to significantly greater resources.

So, you can expect us that we'll invest more than ever than we have done in AI. We're also absolutely not done with our core email experience. We'll be doing a lot more there. We're going to build out calendar and tasks and then connect those beautifully together. We'll also start to spread our wings beyond just emails.

So, we're going to reimagine chat. We're going to redefine collaboration, pulling on everything that we've learned over the last 10 years about work communication. And then, as Shasher mentioned, we are also working on a whole new way of working with AI agents.

Agents that we think will free all of us up to be more creative, strategic, and closer to achieving what we call our human potential. And then just to double click on that a little bit more, uh we really think we're entering the age of agentic computing where AI agents, they're going to work on your behalf.

They're going to reason. They're problem solving and they're incorporating detailed context about your work. They're actually also interacting with other systems and agents. And I think we're we're beginning to see these in some of the products that people are using today.

And for so many people, email is just at the center of where we work. You think about project statuses, customer communication, meeting updates, deal execution, so much more. It all actually funnels through email. Whether it's a system of record or that's actually where the work is taking place.

So we also think that email is the perfect place to deploy a collection and a suite of agents. You can imagine an agent triaging your inbox before you wake up.

You could imagine another agent drafting responses in your own voice and tone incorporating context about you and from your work and at the same time another agent as surfacing insights as scheduling meetings. They're syncing with your other systems of records and your other agents.

Uh and I'll give you a specific and concrete example. Cool. This is something you can actually do in Superhuman today and then I'll talk about how it's going to evolve uh in the very near future. Uh and let's talk about search or or asking your email things.

For over 40 years, we've had to rely on what we kind of hilariously call search. But if you think about what that is, you have to remember senders. You have to guess keywords. You then have to scan subject lines. And now in Superhum, you can simply ask where is the Q3 offsite or what are my flight details?

Uh, and a very real example that uh, blows people away whenever they see it is this thing I do whenever we launch a feature.

Whenever we launch a feature, and you'll know this using Superhum, I send an email to every single person um, who uses the product and then we get a whole bunch of replies back, usually several thousand responses, and I still personally read through every single one.

I reply to some of them, but what I'm doing is I'm copying and pasting my favorite quotes into a Google slide that I can then present at the next company. all hands. Now, this takes half an hour to do properly.

With superhuman today, you can just ask uh what are the top 10 most positive customer responses to the uh calendar see your week launch, let's say, and then boom, boom, boom, boom, boom, immediately within 5 10 seconds, I have the answer.

So, that's taking what is a half an hour task and making it work in five or 10 seconds. Now, we're evolving that so that you can then continue the conversation and take it much beyond email. You can imagine me then saying um okay I want to convey the magnitude of the commercial opportunity to to the team.

So um can you annotate each quote with the name of the person, the company they work for, the size of their current superhuman account and the total number of employees they have and then compute an estimated size of price like how much revenue is there at stake if we were able to sell into that company.

And you can then imagine the superhuman set of agents figuring out what to do with that, realizing the answer actually isn't in your email. It's probably in your CRM. So, a sales intelligence assistant is called into the mix.

There's a handoff between the agents and then the answer is right where I kicked off the conversation in my email app where I happen to spend 3 hours a day. And you can continue the conversation. You can then say, "Okay, let's please turn this into a presentation.

" Uh, and then perhaps it works with, let's say, the Gamma agent to produce an amazing, beautiful presentation in your own brand for the company. And then you might say, okay, I want time to practice this before the all hands. Can you please schedule time in my calendar to do so?

The agent's like, well, you're completely booked it before the all hands. Uh, but we can move some things around. And it's smart enough to know that it's easier to move a one-on-one than it is to move a team meeting. So, it recommends moving the one-on-one. It goes and does that.

And now you have time blocked in your calendar to uh learn a presentation that was created for you in 10 seconds by this agent that just read thousands of email to get the content work that literally would have taken an hour done in let's say one or two minutes. So that's the kind of future we're working towards.

Wild uh there's going to be 250 agent agent startups uh that that are going to hear that and be like damn he's uh they're doing they're doing what I'm what I'm trying to do. This is an ecosystem where we want to put those no to be clear, we want our marketplace to be the place you you deploy those those agents, right?

The the surfaces you want to work on. If if you like, I could talk a little bit about the brand question as well. Yeah, that'd be great. Yeah.

So, and and you know, I I think my experience here is heavily formed by um before starting KOD, I I ran the YouTube group at Google and I think that was one of the best examples of an acquisition that I think flourished in a way that would not have been possible without um without the particular constructs we put in place there.

And there's a lot about that I think that we got right and I think we're I'm going to mimic a lot of that here as well.

Um so in my goal is with Grammarly we're going to build the uh the Aative productivity suite of all the apps and agents that you um that you need some of them that will own some of them that we will be great partners with um but it's really important that each of those retain an identity to and I think that's important because that's how they keep innovating and if you think about uh you know you started using superhum in 2018 you know you were buying into a product but you're also buying into a team and a vision and a feel and all those things really matter and So I I really like this term of building a a comp a compound startup where each of those products still feel like they have an identity, they have a brand, they have a mission, um they have their their they have similarities for things we want to work across, but they have their own perspectives on on the problems that make sense in that in that space as well.

So we want agents to work across all surfaces. It's very important that if I set up my sales agent that it should be able to do um some of the experiences that Rah just described while it's in my email, but while it's in my document, it'll give me a different set of experiences.

When I take it out and and uh use it while I'm using a third party application, it should still be able to bring my context with me. So, there will be things that need to feel similar, but the individual brands will remain separate.

The last thing I'll say about that is the overall corporate brand for Grammarly will change. Uh we're working on a new name for it. Um, so Grammarly will become one of the subbrands itself. We think of it as I was describing, one of the most important agents in that in that platform. So the new brand's coming.

Uh, I'm really excited about it, but uh, not announcing it yet. Yeah, soon. I Yeah, I can't wait to see it. Um, I'm curious how you think about the, uh, the tension between yourselves and someone like a Google, uh, a Google Workspace. Uh, I was joking with John the other day.

It feels like so many companies are so dependent on Google Workspace for the core kind of um just like team management infrastructure that they could just raise the prices every single month and it would take a really long time for even to try to figure out something else.

And it reminded me of of kind of the tension that some of the foundation model labs have today with the app layer above them, although that's quite a bit more intense.

But I'm I'm curious, you know, how deep down the stack you guys would go if you can talk about it or or if it makes more sense to focus on the agent layer or the app layer.

You know, I maybe I can start the it's interesting the three products we're bringing together, Grammarly, Kod, and Superhum all have competed with the Google suite or the Microsoft suite for years. Um, and so I think we're all in the fire. Yeah.

And and I the the thing I'd say about it is it actually comes up less with customers than you would think. Um the I think that when companies decide it's sort of um it's sort of like buying plumbing for your company. You you buy one of these suites.

It covers lots and lots of different uh things, but it these have become a part of the furniture at the at the at the company and people don't really think about them as their real investments in productivity. And so I I totally agree.

By the way, I'm just as this as the way work evolves, imagining trying, you know, setting up every every time you have a I could imagine a world where there's you're you're generating a new agent for a specific task and they have an email and I'm sitting here being like, do I really want to pay, you know, uh Google Worksp every time I spin up a new agent at Google Workspace another $25 a month?

And so I imagine I imagine you guys can take this in a direction that that um kind of reinvents that all of that plumbing in in the long run, but maybe it's not. Yeah. And I mean I would say all three products have found different ways to be better together with the with the underlying products.

Obviously with Grammarly one of its hallmark features that it actually works in all those surfaces.

So it amplifies your investment in you know works great in Google Docs but it also works great in Slack and in Salesforce and all the rest of your products as well um for KOD deeply integrates with those products and then and then for superhuman you know Gmail or Outlook serves as a backend for those those providers.

So, it's it's not really a question of of less investment in in those core uh infrastructures, but if your users want the best possible experience for what they're doing, you're going to go get the best tools.

And in a sort of macro scale, the amount of money you're spending is such a tiny amount of money compared to what what you're actually investing in your employees to go stick another 10, 20, 30 bucks a month for people that you're you're spending hundreds of thousands of dollars on to get them some cases hundreds of millions.

some cases hundreds of millions. Um we're going to have to raise our prices for those employees, but uh you know you're you're going to get a huge return for them and people don't really care that much about their sun cost and their plumbing. Totally. Question. Um I I I I have kind of two somewhat related questions.

One is um I I I don't want to say that, you know, Grammarly is a Chrome plugin, but a lot of people experience that way.

And uh and I noticed I was using a different Chrome plugin and Chrome the Chrome app store like updated and I lost functionality because they changed their policy and this particular plugin wouldn't work in the new rules. And so I'm wondering if this plugin different this is not Grammarly. It was a separate one.

It was called Ublock Origin. It would let me go in and select specific divs on specific websites and basically mute them every single time I hit that website.

It was very very cool, but it was deemed to be like too not like not privacy safe and it was really annoying for me because like I enjoyed this and I was excited to use this thing and then I lost it and I mean I might be able to like download it and sideloadad it or something but it was it was it was difficult and so I'm wondering about like sharp elbows in the because the Chrome plugin is an interesting wedge a interesting go to market.

It unlocks so many different things. because we've seen this with like the OpenAI chat GPT app uh using the ADA or the the the the accessibility features to kind of plug into any IDE on day one.

Like you just have such an interesting ability to plug into, you know, tons of apps with AI in a bunch of interesting ways on and and like you're native there, but it feels like Google might be getting a little bit more sharp elbows there. Has there been any attention there?

Do you think that there will be more over the long term? What are the risks to building on top like building a platform on top of another platform? Yeah, I mean I'll maybe just to to two parts to the answer. First off, just to correct one misunderstanding.

The Chrome plugin is a very big part of the Grammarly um product. Um there's also a desktop application. There's also a set of mobile applications. So iOS and Android. Um and we have millions of users on each of those as well. Yeah.

And uh so but I understand that the product is is synonymous in many people's heads with the with the Chrome extension first.

Um but that's very important because we have to work where users work and sometimes you work in a web browser, sometimes you you know many people use Slack as a desktop app, use Superhuman as a desktop app and so on. So you have to be able to work in those places.

I will say that um staying on that line of where these platforms are is kind of become the core asset of the company.

So that's what I it's kind of what I meant by people misunderstand Grammarly like that I do have a team here that works on being a great grammar agent but a massive team that works on how do we integrate with all these products in a safe and secure way and one of the things we've realized is that we've done this just for the grammar agent but what if we could advertise that across a much broader set of agents and so now if you're if you're someone building a new agent you could go build a Chrome extension a desktop app and so on let's I mean I'll pick I'll pick an example Let's say um I'll pick a book author.

So, you know, I I really like um Kim Scott. She wrote a book called Radical Cander. Um we spent a bunch of time with Kim on right now. She sells a book. You stick it on your shelf. You kind of forget about it.

She wants to build an agent that sits right next to you and says, "Hey, you're not following the principles of the book right now. " Oh, interesting. Yeah.

So, so I'll I'll say it because I'm thinking it, but uh it it seems like, you know, uh I'm going to say this and then I'll provide some more context, but a lot of people uh you know have been very triggered by the marketing that Cle has done.

But at the same time, what what they had surfaced and what you guys had basically started doing years and years ago was was understanding what a user is doing on their screen and starting to surface information and help them take action.

And I think that what you guys are building towards and specifically this app layer on top of this like private secure way of surfacing context will in hindsight be be incredibly obvious that that was how we should be integrating AI in our workday because the idea of like you're working in an app and then you go in another app and you like type a little bit and then you take that and maybe you go back into the other app and then you're just like you know tossing this over the wall makes no sense when things should just be getting constantly served.

This is how this is how people were programming precursor. It was like copy copy the code copy the Python into chat GBT copy the result back and it was like okay there has to be a better way. Yeah.

And and I don't want to tr I I want a I I as a user I would love to be able to have a bunch of different experiences like that but I don't want to trust I don't want to I don't want a hundred different companies to have full read access to my desktop screen and my microphone or or any of these other um things.

So I'm very excited about where where you guys are going. That's exactly right. So it is a it's tense to build a platform on top of your browser desktop so on.

But once we've once we've done that we can now make it available to the Kulies of the world to the Kim Scots of the world so on and say why are you going to figure out how to integrate with every one of those applications and we can do that for you.

You should focus on the logic of what do you want to suggest to the person and when. Yeah totally. I mean couple couple more questions wanted to fire off. uh you guys are well capitalized, you generate a lot of revenue. I'm curious how you're thinking about operating the business on a go forward basis.

I'm assuming you're getting a lot of hopefully getting a lot of efficiency out of AI. So maybe you can uh is the plan to uh focus on innovating while you know generating cash flow or are you guys going to you know uh continue to you know or or just burn and and uh you know run a more traditional valid playbook.

Grammarly has has been lucky to be a cash generating business for a long time. And so it's sort of built into the DNA of the company. Um and so I think in the I I'd like people to start thinking about Grammar with the new brand that we'll announce soon enough.

Um think of us as one of those top few AI companies and you know if you think of the foundation model companies providing great layers for all of us. I I think we're hopefully the suite of applications and agents you really care about with one big business model difference.

We don't burn billions of dollars in order to do it. Um and I think we can hopefully bring that to people in an efficient way which allows us to to grow and expand uh um uh in our own control. Yeah. Last question. Are you guys uh in are you guys talking to more companies? Uh if somebody has if somebody has a