Practical Product Ep 3: The Curse of the 1st PM – Part 1: The Company View with Pulkit Agrawal of Chameleon

Why is it such a struggle for 1st PM hires to succeed? What are the challenges from the perspective of the CEO who hires them? What do founders learn in the experience when seemingly inevitably, the 1st PM they hired with the best of intentions didn’t work out?

Pulkit Agrawal mentioned me and my post on “Why you want to be the 2nd 1st PM” when he lived this challenge firsthand:

And knowing he had just gone through this, I knew we had to talk about it on the Practical Product podcast. That’s why this week’s episode is all about it.

The Curse of the 1st PM – Part 1 w/ Pulkit Agrawal, CEO of Chameleon

If you haven’t read it yet, the best place to start is reading my 2019 post, “Why you want to be the Second 1st PM” to get context on this unique role that comes with special challenges, and sometimes a lot of baggage.

Today’s discussion with Pulkit helps answer the question you may have from the post, “How does this happen?” Pulkit read my blog post, new the risks, and yet it still happened.

Are all 1st PMs doomed? Probably not, but the challenges and unique factors of being an early stage startup do make for an ever-changing set of circumstances that can make someone who was the right choice when hired no longer the right person 6-18 months later.

Pulkit and I have a really candid conversation about what happened, what he learned, and most importantly what he’ll do differently with the second 1st PM (who he just hired).

Highlights of the episode include discussing:

  • (5:35) – How has your approach changed for hiring PM #2?
  • (6:27) – What got you excited about the person you ultimately hired for the #1 role?
  • (13:52) – When did you start to realize things may not be working out?
  • (18:28) – How did you handle the transition of a PM leaving the team?
  • (25:13) – Is it inevitable that the first PM will never be a perfect fit?
  • (34:02) – How are you thinking about changing your hiring process the second time around?
  • (35:44) – What advice would you give a founder who’s considering hiring their first PM?
  • (43:17) – How can the founder set the PM up for success?
  • (45:03) – What advice would you have for PM’s interviewing for a first PM role?
  • (48:52) – What are some red flags candidates need to look out for?

You can also learn more about Pulkit’s company at Chameleon.io, and check out their blog to learn more product management and user onboarding tips.

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2 thoughts on “Practical Product Ep 3: The Curse of the 1st PM – Part 1: The Company View with Pulkit Agrawal of Chameleon

  1. Pingback: » Practical Product Ep 4: The Curse of the 1st PM – Part 2: The PM View with 4-time 1st PM, Hostos Monegro Building Customer Driven SaaS Products | Jason Evanish

  2. Pingback: » Why You Want to be the *Second* 1st PM Building Customer Driven SaaS Products | Jason Evanish

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