Earlier in her career, Horowitz worked as a union organizer with 1199, SEIU, a public defender with the Legal Aid Society, and as a union-side labor lawyer.

An early career misclassification as an independent contractor, rather than a full-time employee, led her to realize the effects of the benefits gap that many freelance workers face in today’s labor economy.

[13] From 2018-2020, Horowitz was the CEO and co-founder of a Sequoia backed startup developing insurtech infrastructure for portable benefits for freelancers.

Trupo developed proprietary short term disability (income replacement) insurance products in Georgia, New York, New Jersey to demonstrate the needed features of the new social safety net.

In recognition of her efforts to create a self-sustaining organization of flexible workers, Sara Horowitz was awarded a MacArthur Foundation Fellowship ("genius" grant) in 1999.

[35] In 2002, she was named as one of Esquire Magazine’s "Fifty Best & Brightest" and received a community development award from the New York Mayor’s Office.