Casey Woo, CEO/Founder of Operators Guild: Strategic Headcount Planning and AI’s Impact on Venture Funding

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Scaling People Podcast

Rasika Rajagopalan

35 episodes

5 days ago

A podcast about the people behind people teams. Join me as I have conversations with other People and Talent Leaders to learn more about their journey, and the innovative approaches they have taken to support, empower, and grow their teams.

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Management

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Casey Woo, CEO/Founder of Operators Guild: Strategic Headcount Planning and AI’s Impact on Venture Funding

Scaling People Podcast

35 minutes 31 seconds

8 months ago

Casey Woo, CEO/Founder of Operators Guild: Strategic Headcount Planning and AI’s Impact on Venture Funding

In this episode of the Scaling People Podcast, host Rasika Rajagopalan sits down with the incredible Casey Woo—5x CFO, COO, and now CEO and Founder of the Operators Guild. Casey has a wealth of experience, having served as Global Head of Strategic Finance at WeWork, CFO at Landing, and as an investor and thought leader helping operators level up across industries.

Join us for a dynamic conversation packed with actionable insights on:✅ Strategic headcount planning for growth vs. profitability✅ The impact of AI on middle management and "The Great Flattening"✅ Building strong partnerships between CFOs and CPOs✅ Metrics that matter for people investments (ARR per employee and more)✅ How AI and operational efficiencies are reshaping funding and the role of operators

Casey’s high-energy approach and deep expertise make this a must-watch for operators, people leaders, and business executives navigating today’s fast-evolving business landscape.