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Lenny's Podcast: Product | Growth | Career

Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam

Lenny's Podcast: Product | Growth | Career

Lenny Rachitsky

Technology, Business, Entrepreneurship

51.5K Ratings

🗓️ 27 July 2025

⏱️ 72 minutes

🧾️ Download transcript

Summary

Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies.

In this conversation, we discuss:

1. The 2x2 framework that identifies your optimal pricing model

2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products

3. Why popular AI coding tools may have already doomed themselves with underpricing

4. The “give-and-get” framework top negotiators use to extract maximum value from every deal

5. The negotiation strategy that helped one founder 4x their deal size overnight

6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything)

7. Why AI companies must get monetization right from day one—not “figure it out later”

8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution)

9. The single question that reveals if your pricing is too complex

Brought to you by:

Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny

DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny

Persona—A global leader in digital identity verification: https://withpersona.com/lenny

Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam

My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation

Where to find Madhavan Ramanujam:

• X: https://x.com/madhavansf

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

• Promo email for Scaling Innovation: [email protected] — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle.

Where to find Lenny:

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

• X: https://twitter.com/lennysan

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

In this episode, we cover:

(00:00) Introduction to Madhavan and his work

(04:30) The core thesis of Scaling Innovation

(09:20) Common traps founders fall into

(12:06) Beautifully simple pricing

(15:00) Mastering negotiations

(26:51) Other strategies for effective pricing and monetization

(27:35) How AI pricing is different

(31:33) Handling POCs

(36:25) The importance of mastering monetization

(38:58) Choosing the right AI pricing model

(43:13) Current trends in AI pricing

(44:48) Strategizing for outcome-based models

(50:23) Packaging strategies for scaling

(51:37) Adapting pricing strategies over time

(53:40) Key axioms for pricing success

(58:00) Takeaways for founders

(01:01:33) Lightning round and final thoughts

Referenced:

• The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan

• Cursor: https://www.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

• Sierra Finn: http://www.sierrafinn.com/

• Chargeflow: https://www.chargeflow.io/

• GitHub: https://github.com/

• Intercom: https://www.intercom.com/

• Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing

• Sierra: https://sierra.ai/

• Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/

Mission: ImpossibleThe Final Reckoning: https://www.imdb.com/title/tt9603208/

• Delphi: https://www.delphi.ai/

• Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/

• Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/

• Lennybot: https://www.lennybot.com/

• Granola: https://www.granola.ai/

• Simon-Kucher: https://www.simon-kucher.com/

• Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/

Recommended books:

Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867

Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060

Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417

Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/

Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.



To hear more, visit www.lennysnewsletter.com

Transcript

Click on a timestamp to play from that location

0:00.0

The good founders need to be able to dominate both market share and wallet share. It is not a choice. You need to get better at both. It feels like every company wants to be an AI company these days. How is AI pricing different? The winners in AI will need to master monetization from day one. If you're bringing a lot of value to the table and you started training your customers to expect $20 a month, then you anchored yourself on a

0:21.0

low price point. You're in trouble. 20% of what you build drives 80% of the willingness to pay.

0:26.2

But the irony is that that 20% is the easiest thing to build often.

0:30.3

What would you say is the biggest lesson you want founders to take away?

0:33.5

If you think about market share and wallet share, let's think about it as a two by two.

0:36.9

The quadrant that you really want to be in is the outcome-based pricing model, the top-right

0:41.6

quadrant where you have great autonomy and great attribution.

0:45.0

About 5% of companies are probably in a true outcome-based pricing model.

0:50.5

If you want to win an AI, figure out a way to get to that quadrant.

0:54.3

Do you feel like the popular IDE startups are going to be in trouble down the road?

0:58.8

Some of them, yes, without naming names.

1:01.9

Today, my guest is Madavan Ramaysham.

1:04.5

Modavon is the smartest person I know on pricing and monetization strategy.

1:09.4

As managing partner at Simon Coucher, he's worked with

1:11.8

over 250 companies, including 30 unicorns to help them figure out how to price, package, and grow

1:17.1

their products. He's also the author of The Book on Pricing, called Monetizing Innovation, and now

1:22.5

he's back with a new book, a sequel, called Scaling Innovation, which teaches you how to architect

1:27.3

your business for long-term, profitable, which teaches you how to architect your business

1:27.9

for long-term, profitable growth. It also how to avoid the common traps that teams fall into

1:32.7

that keep them from building real, durable, sustainable businesses. Bill Gurley wrote the

1:37.1

forward. I had a chance to read an early copy. I absolutely loved it. It's a book that every

1:41.1

founder needs to read. And in this episode, Modavan shares many of the

...

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