Explore every episode of the podcast 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 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.

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!

Join me on this episode of Scaling People as I chat with Lars Schmidt, founder of Amplify Talent and author of Redefining HR. We cover the biggest changes in hiring, the role of AI in recruitment, and how to effectively interview executive-level candidates. Lars shares his expertise on building standout people teams and adapting to the future of work. Tune in for an inspiring conversation with one of the most influential voices in the people space!

In this episode of the Scaling People Podcast, I sit down with Cara Allamano, former Chief People Officer at Lattice and co-founder of People Tech Partners. We dive into her experience navigating "wartime" leadership during layoffs, restructuring, and major transitions, while balancing immediate needs with long-term people strategies. Cara also shares why she founded People Tech Partners—to bridge the gap between HR leaders and the tools they need to lead effectively through tech innovation. With leadership roles at Udemy, Pinterest, and Adobe, her perspective on crisis management is invaluable. Don’t miss this insightful discussion on resilience and the future of HR leadership!

In this episode, Katie Burke, former Chief People Officer at HubSpot, shares insights on supporting entry-level talent in today’s world, emphasizing the importance of sustainable mental health programs, effective onboarding in remote environments, and attracting Gen Z talent. She also discusses the challenges of hiring non-traditional candidates in a remote-first world and the balance between personal and employer brand building for HR leaders. Katie offers valuable advice on continuing to invest in company culture during tough times and navigating career transitions as a Chief People Officer.

In this exciting episode of the Scaling People Podcast, I sit down with serial entrepreneur and investor Spencer Rascoff. Spencer is the co-founder of Hotwire, Zillow, and Pacaso, and is also the founder of the venture capital firm 75 and Sunny. With his extensive background in launching and scaling companies, Spencer has always been known for his people-first leadership approach, well before it became a widely accepted best practice.

Join us as we dive into the philosophy behind his leadership style, explore common blind spots founders face when managing teams, and discuss how people leaders can help drive business success. We also tackle timely questions about scaling companies during economic downturns, the future of the Chief People Officer role, and emerging trends in HR tech. Spencer brings his unique insights from both the founder and investor perspectives, offering invaluable takeaways for entrepreneurs, people leaders, and business executives alike.

In this episode of the Scaling People Podcast, I chat with Mel Steinbach, Chief People Officer at Masterclass. We explore her experience leading people teams at Fortune 500 giants like McDonald's and scaling startups like Cameo. Mel shares insights on balancing innovation and risk, hiring for adaptability, and maintaining mission-driven teams at scale. Tune in for practical takeaways on what it takes to succeed in both corporate and startup environments.

In this episode Sid Pandiya talks about the story and inspiration behind Kona, his company that provides companies a tool to drive conversations around how teams are authentically feeling, and how to best support one another. Sid shares many tips around how managers can generally build trust and psychological safety on their teams, and how Kona leverages their learnings through their platform as they internal build their own company culture. Sid talks about his journey as an entrepreneur and what he's learned as he has built Kona through a time where more and more companies are moving towards distributed or hybridized work. 

In this episode, Emma talks about the evolution of the interview process over the last few years, and discusses what types of qualities employers should be looking out for as they evaluate talent. She gives advice to candidates that are contemplating a career pivot, and shares her personal story around how she managed the pivot from marketing to people operations. Lastly, we talk about strategies to build authentic employer brand, and how to think about creating that through the lens of how you think about branding your product. 

Sean Cervera has been in the diversity space for over 10 years and has a wealth of experiences leading diversity and recruiting initiatives from LinkedIn, Twilio, Uber, SpaceX, Google, and most recently, Curology. Sean talks about the distinction between Inclusive Recruiting, vs. Diversity Recruiting, the former being a philosophy and process towards enabling all candidates to have equitable opportunities, and the later focusing on key outcomes. Sean also talks about the challenges of developing diversity strategies for large globalized companies, and shares insights into how he has approached this in the past. 

In this episode, Claire talks about her inspiration to found AllVoices, a powerful platform geared towards enabling employees to anonymously share feedback with their company’s leadership and people team. AllVoices also provides leaders and People team members the opportunity to respond directly to employees around feedback, opening up conversations and dialogues that may not otherwise have surfaced. AllVoices captures everything from culture feedback, to harassment related feedback, to even Covid19 Health and Safety Related feedback. Claire talks about everything AllVoices has learned about harassment prevention and enablement as her team worked with many companies over the last few years through her product.

GitLab was early in the game in building a fully distributed work experience. In this episode, Darren shares insight into what guided GitLab's initial decision to be a fully distributed company, along with best practices around scaling your remote culture and experience. He discuss the importance of enabling asynchronous work, the value of in transparently sharing your philosophies, and the importance of discussing core values in your hiring process. 

In this episode, Aubrey talks about the power of Equitable Design in making meaningful, impactful, systemic change, and what this looks like at CultureAmp. She also talks about how companies can cultivate belonging as they transition to distributed models for the longer term. Lastly, Aubrey touches on diversity fatigue, the future of DEB, and the role that her own identity plays in this work. 

In this richly packed episode, Archana reflects on her discoveries after sorting through thousands of data points through 2020. She talks about the drivers of burnout risk and how companies can place focus around learning and development to prevent burnout. She talks about the plateau of Diversity Initiatives through the last decade, the re-invigoration of this work in 2020 and the role executive leaders will need to have in driving more change around DEB work moving forward. She talks about the ongoing transition organizations are having from managing through command and control to trust and empowerment and why that’s becoming increasingly important. Lastly, we touch on her experience working abroad in Singapore and how work culture and conversations around work culture are similar/different to her experience in driving this work in the US. 

In this episode, Heather Dunn talks about the distinct role that a Chief People Officer plays in an organization as compared to other Senior People Leader roles. She talks about the role the people team plays in building resilience through an organization and the importance of leading with empathy as exemplified by the distinct approach they took to their performance and compensation review process through the pandemic year. Heather also talks about the tailored support people teams need to consider for their various employee groups and highlights some really great programs they kicked off this year.

In this episode, Ashley provides insights around how people leaders and people initiatives can actually have an effect on the end experience your customers have, ultimately impacting your bottom line. Ashley talks about the balance people leaders need to have in leveraging broad trends and people analytics to inform strategy, with the value in creating individualized experiences for each person within your company. Lastly, Ashley touches on the role people leaders have in helping employees find their "purpose" and "meaning" in their work - and how that can be an incredibly powerful mechanism in driving engagement and overall culture. 

In this episode, Erica Johnson, Head of DEB at Chime talks about the role of the DEB leader within the organization. It goes far beyond internal work - DEB leaders partner with all leaders across the business - marketing, product, tech, people, sales, etc. and centralize conversations around diversity and how these concepts impact every piece of the organization. DEB leaders provide insights around the effects of how you're positioning your product, how you're connecting with your customers, and how you're investing in your internal employees. She also talks about the importance of prioritizing diversity in hiring, building mentorship programs, leveraging data, and celebrating incremental milestones. 

In this episode we dive into the adventure Michelle has had through her career up until her most recent venture of cofounding her own company, Eager Labs! Eager Labs serves to provide organizations and individuals tools to learn together and lead better. Michelle shares some great insights around how to give and receive feedback across all levels - to your own peers, to your manager, and direct reports. She also talks about the importance of cultivating your own authentic leadership style, and how she works with leaders to help them find their own.

In this episode Kerry talks about the transition from Counseling Psychology to the People and Culture world. She also talks about the people team as being a steward of culture vs. as a creator of culture, and how you can enable your organization to drive and take ownership of building something together.

In this episode we learn more about how Wistia approached responding to the pandemic by leveraging a team oriented approach to making decisions and supporting their people. We also talk about strategies to drive inclusion across your organization, and the importance behind finding founders that give people and talent leaders a true strategic seat at the table.

In this episode we dive into how to coach executive leaders as new Head of People. We also talk about what it was like to move from the startup world to joining a company that recently went public! Lastly, we talk about the importance of focusing on your internal inclusion and belonging efforts and before doubling down on your external diversity recruiting efforts. 

In this episode, we talk about the important distinction in coaching vs. consulting, and the ability that coaching has to unlock the potential in your employees. Ellen also talks about what MeUndies has learned about distributed work through the pandemic, and how they've decided to build a return to work plan for the future based on those learnings. 

In this episode, we talk about the story behind She Geeks Out, an organization founded by Felicia and her cofounder Rachel Murray geared towards giving other tech and tech-adjacent womxn and their allies an opportunity to network, learn, and connect with each other as well as with companies who want to hire them. Felicia talks about the evolution of diversity related initiatives over the last 10 years, and advice she has to companies that are just getting started with this work. 

In this episode, we talk about how to build trust and psychological safety as a distributed team by focusing on building strong value touchpoints through onboarding, driving a collaborating vs. co-acting culture, and through intentionally creating forums to have conversations that go a lot deeper than your traditional Zoom happy hour. We also talk about how to provide constructive feedback that is clear yet kind, and how to leverage feedback to build people up vs. create a culture of fear, in a distributed environment.

In this episode, we talk about how to build leadership development programs that are sticky and effective, whether you are designing for new managers or seasoned executives. We also talk about how Gabriela approached her role as joined Drizly, and how she worked with the Drizly team to define their core values, the Drizly DNA. 

In this episode, we talk about how leaders can empathetically support their organizations through change by leveraging the change curve. This curve describes the predictable process we all go through of transitioning from denial, to doubt, to acceptance when faced with new changes. We also talk about how leaders can be more meaningful and effective delegators by using Blanchard’s situational leadership model.

In this episode, we talk about the role of equity centered design and democratic decision making in building a culture of inclusion. Diane shares the importance of reflecting on where power resides within your organization, ensuring that your programs are built around the needs of your employees, and shifting power where it feels unbalanced.