Caroline Payne

I bring nearly 20 years of leadership and management experience across the technology sector and U.S. Navy, along with an MBA from the Kellogg School of Management and formal training in executive coaching through Georgetown University's Leadership Coaching Certificate Program. Most recently, I served as VP of Operations at Fundrise, a technology-driven real estate investment platform, where I led a 60-person business unit with responsibility for business operations, financial performance, strategic planning, and organizational leadership. My work also included developing managers, building teams and functions, leading organizational change, and navigating complex cross-functional challenges. Before Fundrise, I served as a U.S. Navy P-3C pilot, leading teams in demanding operational environments. I flew combat missions and was awarded the Air Medal in recognition of my service. I also served as Division Officer for a 70-person aircraft maintenance organization and as Flag Aide to two Navy admirals. In the latter role, I worked closely with senior leadership to manage priorities, coordinate across staffs, prepare for key engagements, and support decision-making. Over time, I became a trusted advisor, gaining firsthand experience with the complexities of senior executive leadership. Throughout my career, I've worked with more than 60 individuals navigating leadership transitions, complex workplace relationships, competing priorities, and the challenges that come with greater responsibility. My approach is thoughtful, direct, and grounded in genuine curiosity. I help clients step back from the immediate problem, recognize patterns and assumptions, and gain a clearer understanding of the dynamics at play. From there, we focus on what matters most, the choices available, and how to move forward with intention and confidence.