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.
Christine Song, CPO at Knix: the CEO/CPO Relationship
In this episode of the Scaling People Podcast, host Rasika Rajagopalan sits down with Christine Song, Chief People Officer at Knix, to explore one of the most critical dynamics in leadership: the relationship between the CPO and the CEO. With prior roles as CPO at Notch and Coinsquare, Christine brings a wealth of experience in scaling high-growth organizations and working closely with CEOs to align people strategies with business goals. This episode is packed with actionable insights for building trust, navigating challenges, and fostering a strong executive presence.
18 Feb 2025
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.
11 Feb 2025
Jessica Swank, CPO of Box: Rethinking Productivity through the AI Talent Race
In this episode of the Scaling People Podcast, host Rasika Rajagopalan sits down with Jessica Swank, Chief People Officer at Box, to explore the future of HR in an AI-driven world. Jessica, an experienced public company leader with an impressive background at HP and Blue Bottle, shares practical advice on:
- How Box is preparing its workforce for AI integration
- The impact of AI on workforce planning and job roles
- Strategies to attract and retain top AI talent amidst fierce competition
- The shift towards performance-driven cultures and its implications
- Jessica’s approach to driving meaningful change in later-s stage, public companies
- How to set up organizations to adapt quickly to market pivots
- Whether you're navigating the rise of AI or looking to build a more adaptable organization, Jessica's insights are packed with actionable advice for HR and business leaders alike.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
4,657,723,678
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
9 ratings
Spotify
5.0 / 5
11 ratings
Podcast Authority Score: 44 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
30
Social presence
0
YouTube
93
Engagement
51
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