Amy S. Fleming

Amy Fleming is the Chief of Staff at Cock Island Capital, a single-family office in Suffolk, VA. 

Amy joined Cock Island Capital in May of 2022, following a 20-year career in the insurance industry with Bankers Insurance, one of the nation’s largest privately-owned independent insurance agencies. She began her career with Bankers Insurance immediately after college where she started off as an Administrative Assistant in her hometown. After obtaining her Property and Casualty license, she was entrusted with managing a portfolio in the commercial insurance department.

In 2005, Amy relocated to the Bankers Insurance Portsmouth branch where she worked with senior management to establish and oversee the Customer Care Center (CCC), a specialized unit for small business clients. Following four years in this role, she transitioned to the Quality Assurance department where she developed and disseminated reports to support daily operations, conducted internal audits, and facilitated compliance reviews.

In 2019, Amy was promoted to Vice President of Project Management working closely with the Executive Team on multiple acquisitions of agencies across Virginia, West Virginia, and North Carolina. She also played a key role in fostering and promoting the agency's culture, which was particularly vital during the transition to a remote/hybrid work model amid the pandemic.