Jackie Shiff is a lawyer, executive coach and facilitator focused on human and relational intelligence—the capabilities that determine whether teams simply function or truly perform.

Her path has been nonlinear, shaped by moments of change, risk, and uncertainty. Much of her growth has come from transforming vulnerability into strength—an experience that now informs her work with leaders.

Jackie partners with investors, founders, and leadership teams as a trusted confidante, helping them navigate complexity and build the trust, alignment, and accountability required for success. Her approach blends intellectual rigor with deep empathy, enabling leaders to see more clearly, engage more effectively, and make sound decisions when it matters most.

Jackie received her certification in executive coaching from Columbia University and has held leadership roles at the Aspen Institute and the University of Chicago. She is licensed to practice law and served as a judicial clerk to the Honorable Mary L. Mikva.

Most importantly, Jackie ran a very profitable lemonade stand as a kid in Chicago!