Dan Cimaglia is a founding team member at Hera, a NYC startup helping seniors navigate the healthcare system. Prior to joining Hera in 2025, he spent five years at Headway, the nation’s largest network of therapists and psychiatrists who take insurance through their technology platform.

After graduating from Georgetown, Dan pivoted away from trading at J.P. Morgan and decided to enter the startup world. He joined Headway in 2020 as their 20th hire, and by the time of his departure the company had grown to 800 employees. In his first role, he helped scale Headway’s provider sales function, growing its network from 800 providers to what is now the largest behavioral health provider group in the U.S. In 2021, Dan moved to the payer partnerships team, supporting and negotiating Headway’s relationships with health plans. In 2023, he became Chief of Staff to the Chief Commercial Officer, responsible for commercial operations and strategy, Headway’s national expansion, fundraising, and the growth of its payer coverage.

Dan graduated from Georgetown University with a BBA in Finance from the McDonough School of Business and a minor in Psychology. At Georgetown, he served on the board of the Georgetown University Alumni and Student Federal Credit Union. Outside of work, Dan enjoys learning Italian, exploring his home base of New York City, and hiking.

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