Leading with: Authenticity, Curiosity, and Growth with Chelsea Gregory

In this episode of Becoming Better with StartupExperts, Jesse sits down with Chelsea Gregory, Head of Global HR at Suki and one of StartupExperts’ “25 Leaders to Follow in 2025.” Chelsea shares her remarkable journey from teaching in Spain to joining Suki as an office manager in 2018 and growing into a senior HR leadership role. The conversation explores her parallel growth with StartupExperts, her passion for cultivating meaningful employee experiences, and her commitment to supporting teams during rapid scale. Chelsea opens up about personal “cringe moments,” the value of vulnerability, what she’s learned through leading our AI Roundtables, and how embracing humanness is critical to thriving in an increasingly tech-driven world. Chelsea also offers insight into what’s ahead for Suki in 2026, how the organization is preparing for significant growth, and the importance of preserving culture while scaling globally. A thoughtful, grounded, and inspiring conversation—perfect for HR, Finance, and Ops leaders looking to lead with authenticity and curiosity in a changing world.