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How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)

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Oct 5, 2025

Guest

Albert Cheng

Albert Cheng, a growth leader with experience at Duolingo, Grammarly, and Chess.com, shares insights on leveraging user psychology and rapid experimentation to unlock growth. He discusses the explore-exploit framework and reveals how displaying premium features to free users can significantly boost upgrades. Cheng emphasizes the importance of resurrecting dormant users and highlights the value of retention and word-of-mouth for consumer subscriptions. Additionally, he explores the transformative role of AI in product experience and growth strategies.

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Episode notes

00:00 / 00:00

Explore Then Exploit Deliberately

Use an explore-exploit rhythm: explore widely to find human-behavior insights, then exploit by scaling and applying the winning pattern across the product.
Oscillate between phases until exploitation saturates, then return to divergent exploration.

00:00 / 00:00

Game Reviews Grew By Celebrating Wins

Chess.com found 80% of users review games after wins, not losses, contrary to expectations.
They switched reviews to highlight brilliant moves and encouraging copy, boosting reviews 25% and subscriptions 20%.

00:00 / 00:00

Use Experiment Patterns To Guide Strategy

Monitor experiment significance patterns across programs to know when exploitation has been squeezed dry.
If most tests go non-significant, shift teams back to divergent exploration for fresh ideas.

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From Pianist to Growth Leader

04:33 • 5min

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Explore vs. Exploit Framework

09:41 • 1min

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Using Insights to Drive Product-Wide Wins

11:07 • 5min

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Signals for When to Explore vs. Exploit

15:41 • 58sec

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AI for Data, Prototyping, and Discovery

16:39 • 4min

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Grammarly Monetization: Sampling Premium Features

20:57 • 5min

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Why Freemium with Sampled Premium Works

26:01 • 3min

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Retention Is Gold for Consumer Subscriptions

28:32 • 4min

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Resurrected Users Drive Mature Growth

32:27 • 2min

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Differences Between Duolingo, Grammarly, and Chess.com

34:43 • 7min

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Brand, Mascots, and Viral Marketing as Growth Fuel

41:57 • 4min

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How AI Enhances Product Experience at Chess.com

45:56 • 6min

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How AI Changes Growth Work

51:31 • 4min

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Growth's Job: Connect Users to Product Value

55:36 • 1min

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Getting Better at Experimentation

56:37 • 56sec

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Ambition to Run 1,000 Experiments a Year

57:32 • 4min

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Systems, Growth Models, and Experiment Hygiene

01:01:30 • 1min

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Duolingo Virality and Habit Design

01:02:48 • 2min

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Three Pillars of Gamification and Onboarding New Users

01:04:58 • 3min

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Hiring for High Agency Over Experience

01:08:03 • 3min

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Preferred Company Size and Career Stage Fit

01:11:06 • 2min

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Failed Corner: Lessons from a Chariot Product Failure

01:13:35 • 3min

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Reflections on Learning, Reputation, and Giving Back

01:17:00 • 2min

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Lightning Round: Books, Products, and Mottos

Snuggle Puppy! is a bright, chunky board book that serves as a heartfelt love song from parent to child, starring an adorable cast of dogs. Written in Sandra Boynton’s signature playful and rhythmic style, the book is filled with engaging illustrations and bold, colorful text that invites singing or rhythmic reading. Its repetitive, affectionate chorus makes it perfect for bedtime snuggles and helps young children connect with the joy of being loved. The story does not specify the parent’s gender, making it accessible for all families, and its simple, repetitive structure supports early language and print awareness development.

#25147

• Mentioned in 2 episodes

• Mentioned in 38 episodes

Ogilvy on Advertising

David Ogilvy

This book provides comprehensive insights into the world of advertising, covering topics such as how to get a job in advertising, how to choose an agency for your product, the secrets behind effective advertising, how to write successful copy, and the role of research in advertising. Written with brutal candor and generosity, Ogilvy shares his extensive knowledge and experience in the industry, making it a valuable resource for both professionals and those interested in advertising.

Albert Cheng has led growth at three of the world’s most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 experiments a year, discovering counterintuitive insights that have driven tens of millions in revenue.

What you’ll learn:

1. How to use the explore-exploit framework to find new growth opportunities

2. How showing premium features to free users doubled Grammarly’s upgrades to paid plans

3. What good retention looks like for a consumer subscription app

4. Why resurrected users drive 80% of mature product growth

5. Why “reverse trials” work better than time-based trials

6. The three pillars of successful gamification: core loop, metagame, and profile

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Brought to you by:

Vanta—Automate compliance. Simplify security.

Jira Product Discovery—Confidence to build the right thing

Miro—A collaborative visual platform where your best work comes to life

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Where to find Albert Cheng:

• X: https://x.com/albertc248

• LinkedIn: https://www.linkedin.com/in/albertcheng1/

• Chess.com: https://www.chess.com/member/Goniners

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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Referenced:

• How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth

• Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley

• Explore vs. Exploit: https://brianbalfour.com/quick-takes/explore-vs-exploit

• Grammarly: https://www.grammarly.com/

• Reforge: https://www.reforge.com/

• Chess.com: https://www.chess.com/

• Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch

• Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika

• Figma: https://www.figma.com/

• Cursor: https://cursor.com/

• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell

• Claude Code: https://www.anthropic.com/claude-code

• GitHub Copilot: https://github.com/features/copilot

• Noam Lovinsky on LinkedIn: https://www.linkedin.com/in/noaml/

• The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack): https://www.lennysnewsletter.com/p/the-happiness-and-pain-of-product

• Kyla Siedband on LinkedIn: https://www.linkedin.com/in/kylasiedband/

• The Duolingo handbook: https://blog.duolingo.com/handbook/

• Lenny’s post on X about the Duolingo handbook: https://x.com/lennysan/status/1889008405584683091

• The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir

• Duolingo on TikTok: https://www.tiktok.com/@duolingo

• Kasparov vs. Deep Blue | The Match That Changed History: https://www.chess.com/article/view/deep-blue-kasparov-chess

• Magnus Carlsen: https://en.wikipedia.org/wiki/Magnus_Carlsen

• Elo rating system: https://www.chess.com/terms/elo-rating-chess

• Stockfish: https://en.wikipedia.org/wiki/Stockfish_(chess)

• AlphaGo on Prime Video: https://www.primevideo.com/detail/AlphaGo/0KNQHKKDAOE8OCYKQS9WSSDYN0

• Statsig: https://www.statsig.com/

• The State of Product in 2026: Navigating Change, Challenge, and Opportunity: https://www.atlassian.com/blog/announcements/state-of-product-2026

• Erik Allebest on LinkedIn: https://www.linkedin.com/in/erikallebest/

• Daniel Rensch on X: https://x.com/danielrensch

• Chariot: https://en.wikipedia.org/wiki/Chariot_(company)

• San Francisco 49ers: https://www.49ers.com/

• Breville Barista Express: https://www.breville.com/en-us/product/bes870

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Recommended books:

• Snuggle Puppy!: A Little Love Song: https://www.amazon.com/Snuggle-Puppy-Little-Boynton-Board/dp/1665924985

• Ogilvy on Advertising: https://www.amazon.com/Ogilvy-Advertising-David/dp/039472903X

• Dark Squares: How Chess Saved My Life: https://www.amazon.com/Dark-Squares-Chess-Saved-Life/dp/1541703286

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

To hear more, visit www.lennysnewsletter.com

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