Scaling People Podcast

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 operatorsCasey’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.

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.

In this episode of the Scaling People Podcast, host Rasika Rajagopalan sits down with Jeff Diana, former Chief People Officer at Calendly and Atlassian. With leadership experience at Expedia, SAP, and Microsoft, Jeff is a seasoned advisor and board member who helps companies navigate the unique challenges of growth at every stage. This episode is a masterclass in executive team dynamics, leadership coaching, and aligning your team around the business strategy in high-stakes environments.

In this episode of the Scaling People Podcast, host Rasika Rajagopalan sits down with Jevan Soo Lenox, Chief People Officer at Insitro, to uncover what sets the top 1% of people leaders apart. With a career spanning leadership CPO at StitchFix, Minted, and BlueBottle, Jevan shares his insights on everything from navigating crises to driving innovation and leaving a lasting legacy. Whether you’re a CEO, HR leader, or curious about mastering leadership in the workplace, this episode is packed with actionable insights.

In this episode of the Scaling People Podcast, host Rasika Rajagopalan sits down with Liz Simon, COO at Industrious, to explore the evolving workplace landscape. They discuss the future of remote and hybrid work, balancing flexibility with productivity, and how coworking spaces meet the changing needs of businesses. Packed with insights on navigating post-COVID workplace trends, this is a must-watch for leaders shaping the future of work.

In this episode of the Scaling People Podcast, I chat with Marty Reaume, former CPO at Sequoia, Twilio, Fitbit, and NetSuite, about her journey from executive leadership to board membership. Marty shares her insights on landing a first board seat, adapting to influence without authority, and elevating board discussions with people expertise. We also explore the KPIs that matter most in boardrooms and how people leaders can establish credibility across industries. Tune in for practical advice and lessons from one of the most seasoned leaders in the space!

Excited to share the latest episode of Scaling People featuring Priti Patel, Chief People Officer at G2! 🎙️In this episode, Priti and I talk about how to approach organizational transformation when you need to adapt the way you operate to meet the demands of the future. We discuss discuss reshaping leadership, reskilling for the future, overcoming transformation fatigue, and more. Priti shares some personal anecdotes from her time at G2, as well as examples from other companies that have had to make major changes in the way they operate to drive success. Packed with actionable insights, this is a must-watch for HR leaders and execs.

Tune in to the Scaling People Podcast, where host Rasika Rajagopalan interviews Shane Koller, Chief People Officer at Ancestry. Shane delves into the importance of aligning HR metrics with business goals, the challenges of measuring productivity in remote work environments, and how to effectively communicate these metrics to non-HR leaders. He also shares his thoughts on emerging metrics that HR professionals will want to be keeping pulse of.

In this episode of the Scaling People Podcast, I sit down with Donald Knight, SVP of People at Warner Bros. Donald, who has led HR teams across tech, utilities, and entertainment, shares insights on the unique and universal challenges in People and Talent leadership. We discuss the key differences in managing talent in various industries, how to effectively onboard as a new leader in a completely different sector, and the importance of building trust with leadership and key stakeholders. DK also offers valuable lessons on shaping company culture and cross-pollinating HR practices across industries.

In this episode of the Scaling People Podcast, I chat with Lorna Hagen, founder of Win Consulting and former CPO at Namely and iHeartMedia. We dive into the ROI of investing in culture, balancing startup norms without bureaucracy, and how to influence leadership when they don’t see the value of people strategy. Lorna also shares tips for navigating budget cuts without sacrificing engagement. Don’t miss it!