Casey Winters
Casey Winters is a longtime and legendary advisor and operator. He’s worked with companies like Airbnb, Faire, Canva, Whatnot, Thumbtack, Tinder, and Reddit and until recently was the Chief Product Officer at Eventbrite, where he managed the PM, design, research, and growth marketing teams. Before Eventbrite, he led growth and product teams at Pinterest and Grubhub.
AI & Technology Skills
PMs who follow frameworks mechanically will be replaced; those with expertise will thrive.
"If you thought the PM job was just filling in frameworks, you're going to get replaced by AI."
Data network effects create a competitive moat by using proprietary usage data to improve product value, reducing dependence on external platforms like Facebook or Apple.
"What data network effects are, is leveraging product usage data to make the product value stronger and stronger over time... your product being able to generate its own data, versus just relying on th..."
Communication Skills
High-stakes presentations should be de-risked through role-playing and pre-alignment meetings to ensure there are no surprises.
"You want to de-risk that meeting not make it a big success or fail moment... I try to run through it with the team, pretending to be the other members of the audience that are going to be there... The..."
Preparation for a presentation is complete only when you have anticipated and prepared data for every possible question that could arise.
"If you haven't thought through all the questions that might be asked from the document that you're sharing or the presentation you're about to present, you're not prepared enough, right. You need to k..."
Engineering Skills
Securing investment for non-sexy technical improvements requires quantifying their value through custom metrics and small-scale experiments.
"The idea is that some of the most impactful projects that product teams can work on at scale... are the hardest to measure. And because of that, they just get chronically underfunded... I walk through..."
Growth Skills
Product-market fit is a moving target that can be lost if a company fails to keep pace with rising user expectations and competitive improvements.
"Protecting what you've built actually is increasingly important once you build scale... if you're not continually pushing to make your product better... you're eventually not necessarily tomorrow, but..."
True product-market fit requires both a retaining product and a scalable, built-in distribution mechanism.
"Founders are starting to intuit what I've written about a bit as well as you, which is that scalable acquisition or what we call an acquisition loop is a requirement for product market fit. Like if yo..."
Early, non-scalable growth tactics (Kindle strategies) should be viewed as temporary tools to reach the point where scalable loops (Fire strategies) can take over.
"The goal of your Kindle strategies, these like non-scalable hacks, they only exist to unlock the fire strategies, to unlock the things that could take you to millions of users."
Consumer subscriptions relying on paid acquisition will predictably fail.
"If your plan is paid acquisition on top of freemium, I'd pivot right now."
Hiring & Teams Skills
PM interviews reward rehearsed answers over actual job capability.
"The whole thing's gotten so performative. It's like interviewing is handing out Oscars..."
Leadership Skills
Founders should stay directive until hires prove they can make better decisions.
"I need to let these experts own these areas - that's actually the opposite of what you want."
Executives often appear out of touch because teams fail to proactively communicate the context and trade-offs necessary for informed leadership.
"I find that in general people just way under communicate upward inside of companies. And then they'll complain that executives are out of touch when they aren't telling executives what the executives..."
Effective upward communication requires grounding the narrative in high-level strategy (Chapter 1) before diving into the specific work (Chapter 6).
"One of the ways I try to frame it to my team is if you're not an executive, whatever you're working on, you're basically writing and telling a story. And when you talk to an exec about that story, you..."
Upward communication must be tailored to the specific concerns and styles of individual executives rather than treated as a generic audience.
"Something I commonly say is that executive communication is actually executives communication. You're communicating with individual executives that all have different styles and different concerns abo..."
Product Management Skills
The primary bottleneck for career advancement from senior PM to leadership is the transition from execution-focused work to independent strategic thinking.
"The challenge you practically deal with as a product leader is you end up recruiting, and managing, and growing a lot of executional people who can get stuff done, but if they want to get to the direc..."