Leading with: Dave Carhart’s Experimentation, Emotional Mastery & Fractional Leadership

In this episode of Becoming Better with StartupExperts, Jesse sits down with Dave Carhart, one of our 25 Leaders to Follow in 2025 and a long-time contributor to the StartupExperts community. Dave shares his career journey from technical recruiting in Milwaukee to leading HR teams through hyper-growth, IPO, and acquisition — and eventually transitioning into his current role as a fractional CPO and compensation/AI consultant. The conversation explores Dave’s reflections from his time on the StartupExperts Executive Leadership Team, how the community became a lifeline for him during the pandemic, and why emotional resilience and self-management have become central to his leadership philosophy. Dave also dives into his unexpected passion for gardening, the lessons it taught him about patience and limitations, and how those same lessons show up in HR and fractional consulting. Jesse and Dave discuss the evolving role of AI in HR, the mindset shift required to think like a product manager, and the power of experimentation as a career and life strategy. Dave closes by sharing a powerful piece of advice for the community: stay curious, try things, and keep experimenting — especially as AI reshapes the future of work. A thoughtful, candid conversation with a leader who has been instrumental in shaping the StartupExperts community.