The Exchanges

Q trying to build a business on top of consumer subscription. And so I'm just curious. What's the current state of Grammarly? How are things going? Uh, what do you think has been the key to it being successful all this time and, and continuing to grow? And what lessons have you learned? I know you're, you just joined relatively recently, but anything you've taken away from that journey so far?

A We don't, we don't, we don't talk about it often. Um, but, uh, you know, Grammarly is a much, uh, bigger company from a revenue perspective than I think people realize. Uh, you know, the, The, the company has been around for 15 years and was profitable from day one, um, and continues to be quite profitable. Um, uh, so it's a very, very healthy business that is, um, you know, much larger than, than, um, folks might realize. And that is actually quite intentional because the company was trying not to be noticed for a long time, like very intentionally. The fact that, you know, you would have, You know, grammar and spell checking in Google Docs or grammar and spell checking in, uh, you know, Word. People would often write off the company that like, how is that? How is that a business? How is that a feature? Like these products already have it. And you know, the, that was very convenient for, for grammarly, uh, because they could kind of navigate between these giants and tech and grow a very, uh, a very phenomenal business, um, kind of on this, on this use case that people had kind of written off. Now, You know, come the advent of LLMs and it's no longer a use case that people are, are writing off and sort of the, the dream of the, of the founders that machines can assist us in communication in this way, um, that, you know, they've had for 15 years. I feel like now the whole indust…

AI assessment note: “The company has been around for 15 years and was profitable from day one”

Q kill your, kill your career by accident. Like now let's kill this project I'm working on. I'm gonna demote myself a little bit, but clearly it's worked out. Is there anything that you saw that gave you that confidence that this is actually gonna be okay? Because again, people don't normally think this is how you get ahead in your career is you kill your team and you layer yourself.

A Yeah. I mean, I think Having a broader view of the company's strategy, having an instinct for like what we should be doing and why and how I might prioritize all of these investments. Um, if I were given the opportunity to do that, I think like internalizing that and understanding that and then trying to align whatever is under your influence, you know, kind of towards that, um, That, that, that overall goal is very helpful, uh, and, and made me feel like I'm pretty confident this is going to be okay because it will lead to better results for the organization given what we're trying to do. And so as long as I'm trying to push decisions or actions that actually lead to better results, if it's a healthy culture and organization, I should be okay. And I think that the, the other thing is just, just over the years, I, you know, I got extremely lucky. The, the first job that I got out of school was an incredible group of people, and it gave me a nose for talent. It gave me a nose for like what like great feels like and, and what like a high functioning team feels like. And it's hard to like kind of like know that without like experiencing that. And so in, in the, in the moments like, and YouTube was also one of those teams, like Grammarly is one of those teams. Thumbtack was one of those teams. Being able to sniff that out when you're trying to kind of choose the, the next, the next…

AI assessment note: “made me feel like I'm pretty confident this is going to be okay”

Q operate in. Make B to B marketing everything it can be and get 100 dollars credit on your next campaign. Just go to LinkedIn.com slash pod Lenny to claim your credit. That's LinkedIn.com slash pod Lenny. Terms and conditions apply. Is there anything else from your time at Thumbtack that What stands out as an interesting lesson or takeaway that you bring with you to the work you do now?

A I, I would, I would say this, I think, especially, um, especially at the like leadership level, um, you know, in, in the, the, the team that, the team that reports the CEO, um, that, that group. Doesn't always have the opportunity to like do a lot of project work together, right? You've got your, like your CFO, you've, you've got your head, you've got your head of sales, you've got your, Your, your product and your engineering. And there's just not as, as often as sort of like natural ways for that work, that group to work together. Um, and then when something happens, like growth goes negative, um, that group is very important. And that group's ability to like tackle hard things together is very important. And I think that one, one important lesson from that is no one has, no one can be a bystander on product strategy. If you've got, just because you've got product in your title doesn't mean you're the only one that, that should be thinking about product strategy, certainly at that, at that level. Um, certainly not in engineering, like the CFO, the, the head of people, everyone needs to have a seat at the table when it comes to product strategy, what the company's doing and what they're gonna do to kind of, you know, grow out of the situation that, that they're in. Um, because otherwise, like, In those, in those hard times, if it's kind of, it can kind of be like a, you know, …

AI assessment note: “one important lesson from that is no one can be a bystander on product strategy”

Q Next question. Do you have a favorite interview question that you like to ask candidates?

A You know, I generally like interview questions that allow us to kind of like do some work together. So I'm a little bit less on the behavioral, tell me about a time when sort of stuff and, and more on the, like, like let's work a product problem together. Like, and it could be anything from like, let's Design an alarm clock for children or, um, you know, lately I've been using one of like, you know, given, you know, where technology is at, like if we were to rebuild email, like how might we do that? I just feel like kind of getting into it and getting into the details and really kind of watching each other part, you know, kind of exercise our craft, um, I think is, is really important. And I have a, I have a whole podcast one time if you're ready about how Most people don't know how to do leadership recruiting. And I feel like as I've, you know, uh, uh, advanced in my career, like the, the interviews for some reason, like get easier and actually like evaluate less about like, you know, who I am as a, as a product leader or whatnot. Um, uh, but yeah, those, those are the sorts of interview questions that I, I typically like.

AI assessment note: “lately I've been using one of like... if we were to rebuild email”

Q I feel like the advice I always share with people is the best people are not spending time tweeting and talking online, sharing on LinkedIn. They're just doing the work. They don't have time for that sort of thing. And I think you're a great example of that. Is there anything along those lines that you share with folks that are just like, Hey, should I be investing time here?

A I think everyone can chart their own path and has a way that is sort of authentic to them and leans on their strengths. Uh, what, what I often, uh, coach people is like, do what you like. You're, you're generally gonna be a lot better at the things that, like, really fill you up, that really get you excited, and, like, life is short. There's, like, so many things to be doing out there. We're so lucky. Like, the number of interesting waves of technology that I've experienced just makes me feel like it's gonna keep happening for a long time. We're very fortunate to be born in the time that we are and have the opportunities that we are, so why, you know, spend your time doing something that Doesn't feel good because you think that it might, you know, lead to, you know, some, some success where if you lean on what's authentic to you and what is, you know, makes you happy, chances are you're going to be one of the best people at those things.

AI assessment note: “I think everyone can chart their own path and has a way that is sort of authentic”

Q circle back to this first point you made. An experience you had convincing people that your first project shouldn't be something you work on. How long do you stick with something that isn't going well and then decide, okay, let's convince people. This is something I should move on from versus like, you don't want to give up on a project quickly, right? You want to give it a shot.

A I mean, look, I, I don't know that it's a, that it's a perfect answer, but I think the reality is, is that what kills most projects, most early companies is, is stamina. And I think that you, you know, um, we all need to work on, you know, kind of being more resilient about kind of like, I remember at Thumbtack, Marco, the CEO, we used to say that it feels like we're running uphill and chewing glass. Um, and you kind of like, that's right. Like we, we want to do that. Um, that's good. That's good for us. We're take, take our medicine. Um, so you want to, you want to practice that sort of resiliency, but ultimately I think that what, what starts to happen is you, you start to lose the stamina. And you're just not bringing your best self to the, ah, to the, to the situation. And so many of these things that are like so high ambiguity where you, you don't know exactly what to build or you don't know exactly, you're not getting the signal you need or the feedback you need to be able to hone it in and know that you're, that you're, um, uh, doing something well. They require like just an ungodly level of faith and stamina. Uh, and so I, that's, that's sort of like what, what I look to when you see like a team That is motivated. That is building something like they, they're really excited about. I mean, just like the inertia, the, the quality, like just everything. It's just, it's lik…

AI assessment note: “what kills most projects, most early companies is, is stamina”