Sara Ross
Operational Leader / Chief of Staff
Sara Ross
Operational Leader / Chief of Staff
With 20+ years of operational leadership across startups, colleges, and high-net-worth private organizations, I am a proven thought partner and action-leader people count on to synthesize information and get things done. A core distinction of my work lies in the ability to listen to leaders at a level below words and translate vision into action. I thrive in working with people who learn to trust my instincts, bring me into their ideas, and allow me to do more than execute, co-creating in genuine partnership.
Every organization or leader I have worked with has learned to give me more, to lean on me with more responsibility and more trust. From the time I was 19 and tapped to manage a high-grossing retail bookstore, to the college dean nearly 20 years later who created a new role at the university simply so he could have me help him run the show, and the CEO who worked with me for 6 months then invited me into his home to help orchestrate the world of his family, I have been a trusted colleague and leader of people and projects.
I currently serve as Head of Operations for a serial entrepreneur and philanthropist, building the operational infrastructure across a portfolio spanning business and philanthropic ventures. In this role, I work across entities, coordinating operations, finance, and administration for a principal who moves quickly and cares deeply, while increasingly leaning into investor relations as part of the broader mission. This work draws on everything I've built over two decades: the ability to construct systems, hold complexity across many fronts, and earn the kind of trust that expands scope over time.
For the nearly 8 years prior to this role, I served as the operational backbone for a serial entrepreneur across three startups, a private estate, and every complexity in between. I built offices and dismantled them. I managed the financial and operational infrastructure of two high-value private residences. I coordinated legal, HR, finance, facilities, and events, often as a team of one. At my most recent company, with a first-time CEO at the helm, I held the entire operational architecture of the business, allowing leadership to focus on product and people. Each chapter of this work gave me more autonomy, more trust, and more scope than the last.
My education spans an MFA in Creative Writing and graduate work in Library Studies and Counseling Psychology, three fields that appear unrelated until you see what they share. Each one is fundamentally about listening and seeing deeply: how structure builds meaning, how people exist within their own minds and across their differences, how to slot together seemingly disparate pieces of a puzzle. That same capacity is at the core of everything I do professionally.
I am energized by work worthy of my genuine investment: leaders and missions I believe in, where my instincts are trusted and my autonomy is real. I work hard because I legitimately enjoy the feeling of delivering great results; contributing at a high level to people I admire matters deeply to me.