Diana Hamilton

Ms. Hamilton, founded Sycamore Advisors in 2004, following her tenure as Director of Public Finance for the State of Indiana for two gubernatorial terms, overseeing all debt issuance for the various State entities (transportation, SRF, buildings, correctional and cultural facilities). Ms. Hamilton has over 30 years’ experience in investment banking and finance, including time on Wall Street at Salomon Brothers and Goldman Sachs. She serves as lead advisor for a number of large issuers, including State of Illinois, Cook County, Illinois, Chicago Transit Authority, Illinois Finance Authority, Indianapolis Local Public Improvement Bond Bank, Regional Transportation Authority of Chicago, Hudson Yards Infrastructure Corp and the City of Chicago, assisting clients with developing the plan of finance and potential new revenue streams and credits, rating agency strategy and pricing and investor outreach. Sycamore has offices in Chicago, Indianapolis and New York City, intentionally building out an MA practice with a team of seasoned professionals offering specific areas of expertise and high levels of customer service and analytics on a par with the top firms in the industry. Since 2010, Sycamore has assisted clients with over $18 billion in debt issuance, often as the lead advisor. Unique among smaller firms, Sycamore’s clients have been finalists for Bond Buyer Deal of the Year three separate times. In 2019, Ms. Hamilton was recognized as a “Trailblazer” by NE Women in Public Finance. Ms. Hamilton is a graduate of Smith College and holds an MBA from Yale University. She holds both the Series 50 and 54 MSRB certifications.