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Casey Winters6 posts
Casey Winters

Casey Winters

@casey-winters

Serial operator (Eventbrite, Pinterest) who understands how to rise and influence within companies.

#career-development#influence#organizational-dynamics#growth#leadership
Casey Winters
Casey WintersMar 12

The goal of business operations is to not exist.

#leadership#growth#design#strategy#startups#newsletter
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Casey Winters
Casey WintersFeb 24hot take

Most people think being a good leader means handling situations as best you can given the circumstances. Wrong. The right move is often to escalate so someone can help you change the circumstances.

#leadership#growth#design#strategy#startups#newsletter
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Casey Winters
Casey WintersFeb 18

People way under-communicate upward inside companies. Then they complain executives are out of touch — when they're the ones not telling executives what executives need to know.

#leadership#growth#design#strategy#startups#newsletter
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Casey Winters
Casey WintersJan 21

The best way to coach PMs on presentations isn't to debrief after — it's to prepare before. Role-play the meeting, impersonate each executive, and answer their questions before they're even asked.

#leadership#growth#design#strategy#startups#newsletter
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Casey Winters
Casey WintersJan 15hot take

Product ops roles are a hack to deal with a functional issue. That's fine — but if the solution is building larger and larger ops teams, you're not fixing the inefficiency, you're exacerbating it.

#leadership#growth#design#strategy#startups#newsletter
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Casey Winters
Casey WintersDec 31

Executive communication is about finding the last point in your story that's completely obvious to your audience — and starting there. Don't start on chapter 6, but don't re-explain things everyone already knows either.

#leadership#growth#design#strategy#startups#newsletter
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