Headway has raised $325.5 million across six funding rounds, most recently securing $100 million in its Series D round in July 2024, led by Spark Capital at a valuation of $2.3 billion. Founded in 2019, the New York–based company connects patients with in-network therapists while reducing administrative burdens for providers. Earlier backers include Accel, Thrive Capital, and Andreessen Horowitz. The Series D round is focused on expanding into Medicare Advantage and Medicaid, broadening access to affordable mental health care.