Casey Winters
19 statements across 3 episodes · 10 bullish · 5 bearish · 2 people on the record · first statement Jul 21, 2022 by Casey Winters · said 30 times in 15 episodes since 2022 · across every show →
On the record as a speaker too: Casey Winters's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Lenny Rachitsky (18), Timothy Davis (3), Jason Shah (2), Fareed Mosavat (2), Elena Verna (2), Brian Balfour (2), Bangaly Kaba (1)
tap a year for its mentions
2025 1 mention in 1 episode
2024 7 mentions in 3 episodes 2 per episode
2023 13 mentions in 7 episodes 2 per episode
- Understanding the role of product ops | Christine Itwaru (Pendo)
- Brian Balfour: 10 lessons on career, growth, and life
- Leveraging growth advisors, mastering SEO, and honing your craft | Luc Levesque (Shopify, Meta)
- The ultimate guide to product-led sales | Elena Verna
- The ultimate guide to product operations | Melissa Perri and Denise Tilles
- Lessons on product sense, AI, the first mile experience, and the messy middle | Scott Belsky (Adobe)
- How to achieve hypergrowth in your business and career | Carilu Dietrich (Atlassian)
- every mention in 2023, scene by scene →
2022 9 mentions in 4 episodes 2 per episode
- How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable)
- How to build trust and grow as a product leader | Fareed Mosavat (Reforge, Slack, Instacart, Pixar)
- Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)
- Why product-led growth is the future | Elena Verna (Amplitude, Miro, Surveymonkey)
- every mention in 2022, scene by scene →
Everything said about Casey Winters, oldest first
Jul 21, 2022 positive
Winters: Avoiding specialization slows early promotions but speeds executive ascension
“The other element that served me well was just refusing to specialize. I thought if I could learn all the skills that would allow me to combine them to work on the most important things versus only work on the thing I knew how to work on. And that definitely l…”
Jul 21, 2022 bullish
Jul 21, 2022 negative
Winters: Avoid 'big reveal' meetings and de-risk executive presentations beforehand
“I think there's a tendency in product management and product design to want to do meetings where there's kind of this big reveal and an aha to the audience. And it's kind of the opposite of how you want to handle most of these situations. You want to de-risk t…”
Jul 21, 2022 positive
Jul 21, 2022 bullish
Winters: Proprietary product data provides an edge after Apple privacy shifts
“Especially with Facebook and Apple's platform changes, your product being able to generate its own data versus just relying on the big platforms to do all the work for you. That's a real edge that companies are starting to wake up to.”
Jul 21, 2022 negative
Winters: Employees chronically under-communicate upward and unfairly blame executives
“I find that in general, people just weigh under communicate upward inside of companies, and then they'll complain that executives are out of touch, you know, when they aren't telling executives what the executives need to know.”
Jul 21, 2022 positive
Jul 21, 2022 positive
Winters: WhatsApp executes perceived simplicity better than any other company
“The company that I feel like has always done the best job of this is, is WhatsApp where, you know, at its core, it's a chat app and it's really good at being a chat app. But I remember when I went to Brazil, all of a sudden I started receiving like voice messa…”
Jul 21, 2022 positive
Winters: 'Perceived simplicity' hides advanced features until users seek them out
“We strive for this concept of what we call perceived simplicity, which is there are advanced features in the product and they are easily discoverable when you look for them, but they're effectively hidden if you're not looking for them. And of course the major…”
Jul 21, 2022 positive
Winters: Hire full-time growth leads only after finding scalable loops
“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. And it's once you unlock a fire strategy, that's when I think you think about hirin…”
Jul 21, 2022 positive
Winters: CPOs must optimize for the company over their own team
“I think one of the things that's different about being a chief product officer versus, you know, other product rules is how much of a company leadership role it is versus a functional leadership role. You're expected in this role to optimize for the entire com…”
Jul 21, 2022
Casey Winters: Grubhub scaled double-digit million marketing without ops team
“As someone who ran a double digit million marketing budget at Grubhub without marketing ops, because we invested in automation and we invested in process, it scares me when the first tactic people to go to is to add people to help scale.”
Feb 16, 2023 positive
Mar 30, 2023
Winters focuses angel investing on marketplaces and tech debt as a service
“And I'm doing some angel investing and in marketplaces and what I call tech debt as a service, which is, you know, what are startups that are building out things that were hard for my teams in the past to like build or maintain inside previous companies.”
Mar 30, 2023 bearish
Winters: Consumer startups using paid acquisition plus freemium should pivot immediately
“So if what your plan is, is to use paid acquisition on top of a freemium model to get a percentage of people to convert and hopefully stick around forever. I'd pivot right now. Like, I just can't see it working.”
Mar 30, 2023
Winters: High-scale consumer products should test first, research when confused
“The more scale you have, Tends to be, you have less sophisticated customers because you're generally like, you know, consumer thing where the customers are rational. They're not experts. And that's generally where you just try things. You measure the impact th…”
Mar 30, 2023
Winters: Cross-functional teams need a single DRI with no escalation path
“Something we started doing more recently at both Eventbrite and whatnot is just designating the person on the cross-functional team who drives the project. At Eventbrite, we call it the driver. At whatnot, we call it the DRI, directly responsible individual. B…”
Mar 30, 2023 negative
Winters: Consumer subscription startups require 60-70% annual retention to scale
“What that means is you need higher user-based retention. Than a B to B SaaS businesses with more unpredictable users. And it's a lot higher than I think, you know, founders tend to think. We're talking annual retention that needs to be north of 60, perhaps eve…”
Mar 30, 2023 negative
Winters: Paid acquisition efficiency inevitably degrades as startups scale
“Paid acquisition tends to get worse as you scale. You know, you target the best customers first. They have great conversion, great retention. And then as you expand your targeting of new customers, every one of those metrics gets worse until it's no longer pro…”