Cliff is a commercial trial lawyer. Throughout his career, he has focused on commercial contract disputes, class action defense, entertainment and intellectual property litigation (including TTAB and WIPO proceedings), First Amendment litigation, counseling in the areas of privacy and data security, and insurance coverage. He also participated in a year-long fellowship through which he first-chaired criminal trials in San Francisco and Los Angeles. Cliff's clients have included Bob's Red Mill, IBM, Viacom, MBIA, Astra Oil Company, Twentieth Century Fox, Willamette Week, Cornell University, AT&T, Depository Trust and Clearing Corporation, Take-Two Interactive, the American Bar Association, the Anti-Defamation League, and Community Health Plan of Washington.

Prior to joining Sussman Shank, Cliff practiced at Proskauer Rose and Kendall Brill & Kelly, both in Los Angeles.