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Lenny Rachitsky: belief

5 Oct 2025 Lenny's Podcast How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)

“Wow, what a genius move. So essentially, it's here's a bunch of improvements, but you get three, I think max, and then it's like, "Okay, now you get upgrade.”

— Lenny Rachitsky

Source trail

Everything needed to verify it.

Speaker
Lenny Rachitsky
Attribution
Verified speaker
Claim type
belief
Recorded
5 Oct 2025
Publisher
Lenny's Podcast

Transcript context

…And then the second thing, which is I think equally if not more interesting is that I was at this company during this generative AI transformation, which is obviously still going on. And quite frankly, both the company brand as well as the lived product experience for most of the free users was that Grammarly was just a product to fix your spelling and grammar because those were the free suggestions we were showing people. And so we decided to flip that on its head entirely and we said, "Okay, what if we actually sampled a number of different paid suggestions and interspersed them to free users across their writing?" Such that they were intermingled and we would provide a limited taste of what the paid offering had to provide. And on the surface, even though it's rational, the concern is that if we give too much of this away, then will people want to subscribe? And we found completely that was not the case all of a sudden, people were seeing Grammarly as a much more powerful tool than they were before and our upgrade rates nearly doubled just through this change. And so I think this is interesting, just modernization learning that especially if you work on a freemium product, try to have your free product be a reflection of everything that your product can offer you. Obviously to an extent there's some costs involved with some of the paid features and things like that, but it generally will pay for itself if you're able to put your best foot forward and go do that. So that really worked well for us there. I think this is what converted me to being a paid Grammarly subscriber. Wow, what a genius move. So essentially, it's here's a bunch of improvements, but you get three, I think max, and then it's like, "Okay, now you get upgrade. " It's basically a reverse free trial but in real time while you're writing as opposed to a time-based one. So we adopted some patterns that are in the industry, but molded it to Grammarly's specific use case.…

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