Pepper Sleight

Pepper Sleight is an experienced underwriting professional with a career spanning over a decade in various leadership roles within the insurance industry. Currently serving as Senior Vice President of Underwriting at Rokstone Underwriting since February 2025, Pepper previously held positions at Hudson Insurance Group as Head of GL Binding and Programs from April 2023 to February 2025, and at Berkley Aspire as Vice President of Strategic Initiatives, AVP of Operations, and Director of Underwriting Services from March 2015 to April 2023. Earlier experience includes roles as Underwriting Services Manager at W R Berkley- Berkley Regional Specialty from 2011 to 2015, Underwriting Services Supervisor at Berkely Regional Specialty Ins Co in 2010-2011, and Senior Agency Relations Representative at Berkley Regional Specialty Insurance Company from 2009 to 2010.