Punctuation Preferences and Perceptions in Writing

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.

What you will learn:

1. Why do most marketing playbooks often fail, and what’s a better way?

2. Which marketing lever should I pull first?

3. Why is trying to be better than competitors usually a losing strategy?

4. How do I craft positioning that actually converts?

5. What makes messaging stick with developers, enterprises, and consumers?

6. What pricing experiments actually move revenue?

7. What is working at OpenAI really like?

8. Why does consistency and quality matter more than speed?

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Where to find Krithika Shankarraman:

• X: https://x.com/krithix

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

• Website: https://krithix.com/

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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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In this episode, we cover:

(00:00) Introduction to Krithika

(04:22) Early marketing lessons from OpenAI

(11:17) Diagnosing marketing needs

(15:06) The DATE framework and why being cheaper is a race to the bottom

(17:11) Marketing strategies at Retool

(22:29) Insights from marketing at Stripe

(32:33) The importance of consistent marketing communication

(39:55) Criteria for hiring a marketing expert

(41:43) “Capital M” vs. “lowercase m” marketing

(43:05) ChatGPT vs. Claude: market dominance

(45:31) The future of AI and its societal impact

(47:09) Work-life balance

(48:41) Transitioning to Thrive

(52:35) Career advice for marketers

(55:00) The importance of taste and creativity in the AI era

(01:00:04) AI product pricing

(01:03:21) AI tools in marketing

(01:05:17) Failure corner

(01:08:46) Lightning round and final thoughts

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Referenced:

• OpenAI: https://openai.com/

• Stripe: https://stripe.com/

• Retool: https://retool.com/

• Dropbox: https://www.dropbox.com/

• Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew

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

• Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy

• Netflix: https://www.netflix.com/

• Stripe Connect: https://stripe.com/connect

• John Collison on X: https://x.com/collision

• Patrick Collison on X: https://x.com/patrickc

• Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/

• Hackpad: https://en.wikipedia.org/wiki/Hackpad

• Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg

• Wiz: https://www.wiz.io/

• Thrive Capital: https://thrivecap.com/

• Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach

• Claude: https://claude.ai/new

• ChatGPT: https://chatgpt.com/

• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

• Databricks: https://www.databricks.com/

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

• Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• Severance on AppleTV+: https://tv.apple.com/us/show/severance/

• Granola: https://www.granola.ai/

• Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/

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Recommended books:

• Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005

• Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/

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

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Lenny may be an investor in the companies discussed.

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