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Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)

Jason Shah has led product teams at Amazon, Airbnb, Microsoft, and Yammer and currently leads the product team at Alchemy (one of the most important web3 infrastructure companies). In addition, he’s an advisor, investor, and two-time founder. In today’s episode, Jason discusses what it’s like to be a PM in web3, why his role at Amazon made such a big impact on his life and career, what makes a great leader, and how to hire well. He also shares his unique perspective on building a meaningful career and life. Find the full transcript here: https://www.lennysnewsletter.com/p/building-a-meaningful-career-jason — Where to find Jason Shah: • Twitter: https://twitter.com/jasonyogeshshah • LinkedIn: https://www.linkedin.com/in/jasonyogeshshah/ • Website: https://www.jasonshah.me/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • Twitter: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Thank you to our wonderful sponsors for making this episode possible: • Whimsical: https://whimsical.com/lenny • Coda: http://coda.io/lenny • Amplitude: https://amplitude.com/ — Referenced: • Creative Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs: https://www.amazon.com/Creative-Selection-Inside-Apples-Process/dp/1250194466 • Casey Winters on Lenny’s Podcast: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within#details • Jason Shah in Lenny’s newsletter: https://www.lennysnewsletter.com/p/a-product-managers-guide-to-web3 • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 • Polygon: https://polygon.technology/ • Solana: https://solana.com/ • MoonPay: https://www.moonpay.com/ • The Vietnam War series by Ken Burns: https://www.pbs.org/show/vietnam-war/ • Alchemy: https://www.alchemy.com/ — In this episode, we cover: (00:00) Jason’s background (08:19) The current state of web3 (12:44) The evolution of product management in web3 (15:27) The value of a great product manager (18:11) Why Amazon was a great learning experience  (20:25) A look into Amazon’s process on working backward (23:55) How to communicate clearly (28:17) Working backward from excitement (32:46) What makes a great leader (38:26) How to influence a CEO or founder’s direction  (46:19) The career ladder vs. career map framework (52:27) When to follow a new opportunity vs. when to stick it out (58:50) How to hire the right people (1:03:47) What skill is most important for product managers (1:06:49) Lightning round! — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Jason ShahguestLenny RachitskyhostJon (from Amplitude)guest
Sep 17, 20221h 10mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

From Web3 winters to career maps: building meaningful product careers

  1. Jason Shah, product leader at Alchemy and veteran of Airbnb, Amazon, Microsoft, and Yammer, shares how to build a meaningful, resilient product career. He contrasts Web3 hype cycles with real product progress, explains how PMs can keep teams motivated during downturns, and describes the evolving role of product management in crypto. Jason also dives into Amazon’s working-backwards process, what great leadership looks like up close, how to effectively “push back” on CEOs, and his ladder-vs-map framework for long-term career decisions. The conversation closes with practical advice on hiring, defining the right problems, and choosing when to stay versus when to take a risky leap.

IDEAS WORTH REMEMBERING

5 ideas

Progress, not pep talks, is what sustains morale in downturns.

In volatile environments like Web3, shipping real improvements, seeing customer usage, and attending active builder events do more to keep teams motivated than speeches or short-term incentives.

The Web3 PM role is maturing and becoming more traditional.

Early crypto products often grew without PMs, but as products gain complexity and competition intensifies, companies like Uniswap, Gemini, and OpenSea are now hiring experienced PMs and product leaders across levels.

Amazon’s working-backwards process forces clarity of thought.

Writing a PRFAQ—press release plus internal/external FAQs—with concrete language, numbers instead of vague adjectives, and specific customer and leadership quotes clarifies what you’re building, why it matters, and how it will launch.

Great leaders are humble, in the details, and adaptable.

Across Bezos, Chesky, David Sacks, and Alchemy’s founders, Jason observes three shared traits: nothing is “beneath” them, they deeply audit real product/customer details, and they change course as new information emerges.

Effective ‘pushback’ starts with reframing goals, not saying no.

Instead of treating pushback as confrontation, Jason aligns with the CEO’s underlying objective (e.g., a magical experience, winning the market) and reframes the proposal—like “trip designers” instead of concierges—so everyone gets a better path to the same goal.

WORDS WORTH SAVING

5 quotes

The only way to maintain morale is to make progress.

— Jason Shah

Product is always a competitive advantage. It improves strategy, execution, and team collaboration.

— Jason Shah

Nothing is above them. The best leaders aren’t above a product spec or running a query.

— Jason Shah

Pushback starts from ‘I need to say no.’ Instead, ask, ‘How do I help the business actually succeed?’

— Jason Shah

I care more about living a really interesting life than a comfortable life.

— Jason Shah

State of Web3 and the evolving role of PMs in cryptoMaintaining team morale and focus through boom-and-bust cyclesAmazon’s working-backwards (PRFAQ) process and writing disciplineTraits of highly effective leaders and founder involvement in productHow to productively “push back” on CEOs and foundersLadder vs. map: a framework for long-term career designHiring as marketing, sales, and product; and problem-definition as a core PM skill

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