Houssier: Grammarly captures cross-app context that ChatGPT cannot access
“Grammarly knows, basically, where you, I say, you're switching from Google Doc to Salesforce. To LinkedIn, and now you're writing an email. So we have this augmented context even more, so like much more precise compared to something like ChatGPT, for example. …”
Sam Lessin: Grammarly is completely destroyed by AI
“It's a great example, if you think about Grammarly, of a company that is completely fucked by AI, right?”
Cheng: Over 90% of Grammarly users are on the free tier
“The Grammarly is a freemium business model, which means that over 90% of our users are on the free service and the rest of it pay for subscriptions essentially.”
Grammarly nearly doubled upgrade rates by sampling paid features for free users
“All of a sudden people were seeing Gramly as a much more powerful tool than they were before, and our upgrade rates like nearly doubled just through this change.”
Consumer freemium works best when core features are permanently free
“So I think these things are usually why I lean toward make sure that the core value proposition that you're providing users is free and is sort of permanently free. And then you layer on kind of a sampling or a taste of some of the premium features that are on…”
Background utilities rely on activation aha moments far more than daily retention
“One exception is that Grammarly was a different type of product and that you install it and you don't proactively open it every day. So that was kind of interesting to me because I assumed that you should always just focus on existing user retention, but for a…”
Isenberg: Seat-based SaaS pricing will become less common
“Seat-based, which is Slack, Figma, Grammarly. I think this is gonna be less and less common.”
Calacanis: Superhuman reached $825M valuation and $35M annual revenue
“Superhuman had raised a hundred and fourteen million. It was valued at eight hundred and twenty-five million during peak Zerp. According to Reuters, Superhuman has annual revenue of thirty-five million dollars”
Grammarly raised a $1B non-dilutive loan from General Catalyst
“Grammarly just raised a billion in, everything about it was weird, like, non-diluted funding. It's basically a loan from General Catalyst.”
Roy: Grammarly secured $1B non-dilutive capital from General Catalyst
“Grammarly did not raise one billion dollars in the traditional sense we all talk about of equity. They secured a one billion dollar commitment from General Catalyst's Customer Value Fund, CVF. The way this money works is it's non-diluted, it's not equity, it d…”
Kantrowitz: Grammarly will go extinct as LLMs replace grammar tools
“And here's my hot take on Grammarly. I think they're going to go extinct. I think I wouldn't call them a rapper because they were around before large language models, but all this logic that they painstakingly built into their program and all the AI developmen…”
Yamashita: Shishir Mehrotra excels at intentionally designing organizational culture
“He's such an incredible systems thinker. He just knows how to run an organization, and he obsesses over rituals and basically kind of designs. I think a lot of times, you know, you think about building a product and designing a product, but he also thinks abou…”
Park: Paying $20k-$30k for YouTuber sponsorships will never yield positive ROI
“You can pay them, you know, literally one 100th of the price to sponsor because these YouTubers, they're kind of, they've been spoiled by the Nord VPNs and the Grammarly's and the, you know, the Sony sponsorships. They expect like 20,000 dollars for a 32nd You…”
Newton predicts Grammarly will be dead by the end of 2025
“Oh, can I give you a prediction? Grammarly dead by end of 2025.”
Hays: Grammarly is at roughly $300M in ARR
“I saw that Grammarly is at, like, basically, three hundred million of ARR.”
Hays: Much more bullish on Duolingo than Grammarly due to platform risk
“Like, I actually am more bullish on Much more bullish on Duolingo than Grammarly when Grammarly feels like, okay, you're built on top of this browser that actively wants to roll out features that differentiate it from all these other browsers.”
Roy-Chowdhury: Remote work accelerated the critical need for asynchronous written communication
“Teams have become more distributed and more global. And through the pandemic, it accelerated what is all, what had already been something that is in progress, which is more remote work. And more sort of distributed teams communicating increasingly asynchronous…”
Roy-Chowdhury: Grammarly saves workplace users an average of 19 days annually
“As one data points on average a person who uses Grammarly at work, Saves 19 business days per year, per user, per year.”
Roy-Chowdhury: LLM boom triggered Grammarly's product rethink and CEO transition
“When LLMs became widely deployed, I saw that as a massive tailwind that increased the ability for us to deliver an incredibly powerful solution to our users. So right around the time when LLMs were becoming widespread and we could all see that this was an oppo…”
Roy-Chowdhury: Massive compute and data powered statistical AI's triumph
“Back in the nineties, it was very unclear that the statistical approach would actually be the one that won out, but it did. And I think the answer is exponentially larger amounts of compute, exponentially larger amounts of data unlock Incredibly high fidelity …”
Roy-Chowdhury: Grammarly shifted focus from individual subscriptions to enterprise demand
“We had historically been focused on individual users buying premium subscriptions, but increasingly we were seeing a lot of demand for Grammarly inside the enterprise.”
Roy-Chowdhury: Grammarly allows all users to opt out of model training
“We have the opportunity for every single user of Grammarly free or paid individual or business to opt out. Of using Grammarly, using their data to train Grammarly's models.”
Roy-Chowdhury: Grammarly open-sourced sensitive text classifier project Seismograph
“We have built, for example, a sensitive text classifier. It's a project that we call Seismograph and we've open sourced it.”
Roy-Chowdhury: Grammarly in active talks with hundreds of universities on AI
“We are in active conversations with hundreds, literally hundreds, maybe thousands of universities across the US, across the world, all grappling with this question of this is big technical shift.”
Roy-Chowdhury: Grammarly education feature cites student AI prompts
“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 your, you're writing a term, you're writing an essay or doing some other piece of work product for your
Fo…”
Roy-Chowdhury: Grammarly uses LLMs to expand across the entire communication lifecycle
“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 kind of help people along the full spectrum of this communication journey. Now with large l…”
Roy-Chowdhury: Grammarly aims to improve every workplace conversation, including video
“Eventually our ambition is to make every conversation better. So that's where Grammarly is headed.”
Roy-Chowdhury: Grammarly pulled service from Russia over Ukraine invasion
“We paused, we canceled Grammarly availability in Russia and Belarus because there was active military operations against people that we knew who are colleagues of ours in harm's way.”
Conover: Financial AI requires deep domain expertise for non-consensus insights
“Grammarly is a good example of a company that has Generative work product that is valuable by most humans. Whereas in finance, the character of the insight, the depth of insight and the non-consensusness of the insight really requires fairly deep domain expert…”
Lovinsky: Grammarly was profitable from day one and remains profitable
“The company has been around for 15 years and was profitable from day one and continues to be quite profitable.”
Lovinsky: Bootstrapped culture can hinder companies needing to invest ahead of growth
“In moments that were like in, in that we're in like today, that can also be detrimental. Right. Cause like the business gets to a certain size. You start getting to kind of like log large numbers. You need to start thinking about, you know, are there other pro…”
Lovinsky: Arc browser makes it difficult for Grammarly to work
“I think there's a few things that the Arc browser is doing that make it hard to get Grammarly to work either on the client or in the browser.”
Rosenberg: Early-stage startup products never sell themselves despite founder claims
“And as much as the founder who sells you into the job says, there's product market fit, we figured it out, it's gonna be glorious, all you have to do is work, walk into the market and it'll sell itself. Well, it never does. It just never does.”
Rosenberg: Startup founders are too close to product to build sales playbooks
“They have superpowers in lots of areas, but my point of view is building a playbook ain't one of them. And let me explain. I think you need a level or a layer of abstraction to be great at building a playbook. Now founders are so close to their business. They'…”
Matt Rosenberg: Sales is translation between buyer language and product strategy
“The challenge of sales is translation, right? You have to translate what you do in a way that the buyer can hear it. And you need to take the buyer's language and translate it back to the company in a way that company could hear it. That translation is what's …”
Rosenberg: Early-Stage Startups Must Record and Collectively Review Every Sales Call
“There is no reason every call shouldn't be recorded. There is no reason that every call shouldn't be listened to together. If it's sales leader and two, three in a box in a room breaking down the call, it's like any athlete breaks down tape.”
Rosenberg: Software sales discounts over 10 percent signal underlying pricing issues
“A discount is a concession, so you could start from a place of any discount you want to contain, because you really shouldn't discount your product if you're solving Customer issues and you're pricing it appropriately. But I would say like, you know, 10 to 15%…”
Matt Rosenberg: Grammarly's CEO recruited me via a cold email
“I actually came to Grammarly in the most unusual ways. I got a email, a cold email from the CEO of Grammarly, and the CEO of Grammarly reached out to me with a very precise message. His interest in talking to me Because of a number of different reasons based o…”
Matt Rosenberg: One third of Fortune 500 companies deploy Grammarly
“A third of the fortune 500 use and deploy Grammarly today.”
Rosenberg: Gong executed an exceptional strategy in defining its market
“I think you'd have to look at Gong. I'm just amazed at what Gong's done. Now it's very common in my profession. Everybody records calls. Everybody breaks down the calls. Every sales leader leverages the application. So kudos to them for not only creating the t…”
Meta, Bloomberg, and Grammarly Are Paying Enterprise Customers of Hugging Face
“3000 companies are paying us for that, including Meta, including Bloomberg, including Grammarly and companies like that.”
Grammarly scaled to massive success almost exclusively through paid acquisition
“And I think there's some really great examples Of companies that have scaled, you know, in relatively recent times, almost exclusively through paid, like Grammarly is a really good example of this.”
Hoover: Grammarly serves over 50,000 enterprise teams globally
“We help over 50,000 teams improve their communication and drive results at about as many companies globally.”
Hoover: Grammarly has over 30 million individual users
“We also help over thirty million individuals improve the quality and impact of their writing so they can accomplish their goals and live fuller lives.”
Hoover: Grammarly has been cash flow positive almost since inception
“We've been cash flow positive pretty much since inception.”
Hoover: Asynchronous communication eliminates critical real-time nonverbal calibration
“The challenge with this communication is we lose the nonverbals that we get when we're talking to someone in person. And so we can't calibrate how our message is landing And adjust what we're saying or ask follow up questions to make sure that our points actua…”
Hoover: US businesses lose $1.2 trillion annually to ineffective communication
“In that pool, we learned that just US businesses, which is a small fraction of global communication, lose over a trillion dollars a year, 1.2 trillion, to ineffective communication.”
Hoover: ML apps create compounding data network effects for early movers
“Certainly an example of applications that do are machine learning powered applications that have data network effects. Grammarly is an example of that. In our case, as an early mover, that enabled us to really build a very high quality set of suggestions to dr…”
Hoover: Engagement data misleads if current users do not reflect future users
“First off, you need to think about the users that you have and whether or not they're representative of the users you expect to have in the future. If they're not, you're looking in the rearview mirror.”
Hoover: Grammarly chose end-user subscriptions from early days to ensure alignment
“Going back to the very early days, we wanted to align our interests with our users, and we did that by selecting a business model where we're only paid, in our case subscriptions, by our end users.”
Hoover: Grammarly took three years to build its first freemium version
“In Grammarly's case, it took us three years to build the first version of our freemium model. We did that from 2012 to 2015.”
Hoover: Organizations break at 5–7 and 150 employee thresholds
“As you move beyond five or seven people you know, things break. As you move beyond a 150, you have another break point, and so you want to make sure that you have a plan to address that as you scale.”
Hoover: Breakthroughs come from novel user nuances, not standard personas
“When we're talking to individual users, it's very easy to just bucket those users in the personas or segments that we've identified. But the value of those conversations and the breakthroughs comes in the difference between what we know and that person's persp…”
Hoover: Grammarly had accounts in half of Forbes 2000 before enterprise sales
“We had individual accounts in about half of the Forbes 2000, which was something we felt great about, but we weren't getting these wall to wall implementations.”
Hoover: Grammarly scaled enterprise sales separately before reintegrating it
“As we made the decision to build out our Grammarly business sales organization, we decided to carve much of that out into a separate group with a separate senior leader to build it up to a level of scale. And then to integrate it back into the rest of Grammarl…”
Timen: Disciplined companies like Grammarly will win from ad market contraction
“But even right now, during contraction, there are going to be some winners. The companies that had strong cash positions, had strong unit economics, strong payback periods already, right? Grammarly, Canva, to name two that I know personally, a couple of others…”
Timen: Grammarly was over-reliant on performance marketing before diversifying
“In the case of Grammarly, it was performance marketing, kind of over-reliance on performance marketing during, you know, part of the company's life cycle. And so it was like, okay, this thing is working. It's efficient. So you don't want to stop pouring fire o…”
Grammarly raised its first $120 million without disclosing its valuation
“Yeah, that was yeah, that was 120 and we didn't disclose valuation at the time.”
Grammarly publicly disclosed its $13 billion funding valuation
“So we raised at thirteen billion valuation, and we disclosed that valuation.”
Max Litvin believes Grammarly's $13 billion valuation is conservative
“I still think it's a conservative, it's conservative one.”