20Product: When to Hire a Product Manager, The Three Different Types of CPO, How To Know What You Need, How To Structure the Hiring Process, What Are the Must-Ask Questions, What Tests and Case Studies Should Be Used, How Should Their Compensation Package Be Structured and more...

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org where she constantly had to navigate the process of how to hire a product manager. 

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter.

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos.

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay.

Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. 

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 one of the most popular newsletters on Substack. 

For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015.

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012.

In Today’s Episode on How to Hire a Product Manager, We Discuss:

1.) When to Hire Your First PM:

• What are the core signs that the founder must delegate and hire their first PM?

• What are the first things that are breaking when you do not have one but need one?

• How does the timing of the first PM differ when comparing B2B vs B2C?

2.) What is the Right Profile:

• What should founders look for in this first PM hire? What traits make the best?

• What are the biggest red flags in the personalities and styles of potential candidates?

  • Should they have experience in the product domain they are entering?

• What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume?

3.) The Hiring Process: How To Hire a Product Manager

• How do we structure and run the hiring process for this person?

• What tests can we do to understand if they have the skill set we need for the role?

• How do we structure a hiring panel to make this process more effective?

• What are the biggest mistakes founders make in the hiring process for PMs?