The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

20 Product: Lenny Rachitsky on The 3 Key Roles of the Product Manager, 5 Skills All The Best PMs Have, When To Hire Your First PM, How to Structure the Hiring Process for PMs & What Leaders Can Do to Make Their PMs Successful


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Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here.

In Today’s Episode with Lenny Rachitsky You Will Learn:

1.) Origins in Product:

  • How did Lenny make his way iunto the world of product management at Airbnb?
  • What were some of his biggest takeaways from his time at Airbnb on product?
  • What mistakes did he make on product at Airbnb? How did it impact his product thinking?

2.) Product Management: 101

  • How does Lenny define product management today? How is the role of PM changing?
  • When is the right time to hire your first PM as a startup?
  • What is the difference between Head of Product and CPO? When do you hire each?
  • What are the biggest mistakes founders make when hiring their first product hires?

3.) The Hiring Process:

  • How should founders breakdown the process of hiring for their first in product?
  • What does the interview process look like? How should founders structure it?
  • What core questions should teams ask of prospective candidates?
  • What are red flags when interviewing potential product hires?

4.) The Onboarding Process:

  • How should founders structure the onboarding process for new product hires?
  • What can founders do to make PMs successful in their first 30 days?
  • Where do many product hires make the biggest mistakes in the first 30 days?
  • What can product hires do to build trust with their new team?

Items Mentioned in Today's Episode with Lenny Rachitsky

Lenny's Fave Book: The Mom Test

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The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The PitchBy Harry Stebbings

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