Prior to joining CHCF, Sherman was a legal editor and managing editor of Internet products for Nolo Press, a publisher of self-help legal books and software, where his work centered on educating consumers about personal legal issues. He was the editor of Nolo's Guide to Social Security Disability: Getting and Keeping Your Benefits; Beat the Nursing Home Trap; Child Custody: Building Parenting Agreements That Work; and Social Security, Medicare and Pensions, among others.

As a filmmaker and journalist, he covered the US Supreme Court, served as a foreign correspondent in Asia, and was a television executive in Japan. Sherman earned his bachelor's degree in American studies and political science from the University of California, Santa Cruz.