In February 2022, True Wind made a growth equity investment in Sterling to help the company leverage technology to capitalize on the large and growing demand for customizable and affordable group benefit insurance options for Canadian businesses. The investment was Sterling’s first institutional capital. True Wind developed a value creation plan aimed at establishing the infrastructure to support the company’s rapid growth and identifying new organic and inorganic growth opportunities. The partnership between True Wind and Sterling helped Sterling focus on growing its business while implementing the operational rigor to support clients at scale. In October 2025, Sterling was acquired by HGGC, a Palo Alto-based private investment firm.