After serving at the SEC and FINRA, Carlo di Florio left the regulatory world to join ACA Compliance Group (ACA) as a partner and global chief services officer. Joining the SEC’s Office of Compliance Inspections and Examinations (OCIE) in the wake of the financial crisis, di Florio oversaw a comprehensive review and transformation of the National Exam Program, and at FINRA, he was responsible for oversight of key functions such as risk management, regulatory programs and data analytics. The Hedge Fund Law Report recently interviewed di Florio in connection with his move to ACA. This first article in our two‑part series covers his move to the private sector; his experience at the SEC and FINRA; and the relationship between OCIE and the Division of Enforcement. The second article will discuss his time at OCIE reviewing and redesigning the National Exam Program; the impact of technology on the exam program; the benefits of regulatory transparency; and the challenges faced by chief compliance officers. For coverage of di Florio while he was at the SEC, see “OCIE Director Carlo di Florio and Asset Management Unit Chief Bruce Karpati Address Examination and Enforcement Priorities for Hedge Fund Managers at the RCA’s Compliance, Risk & Enforcement 2012 Symposium” (Jan. 24, 2013); and “SEC’s OCIE Director, Carlo di Florio, Discusses Examination Strategies and Expectations for Impending Examinations of Private Equity Advisers” (May 10, 2012).