Understanding the impact of cyber attacks on our financial system remains an essential goal for the private sector, policy-makers and academic researchers. MIT, the Federal Reserve Bank of Richmond, and the Federal Reserve Board are sponsoring a multi-part series dedicated to exploring the relationship between cyber incidents, measurable associated losses, and cyber risk modeling. For this initial, smaller session, subject matter experts from financial services firms (banks, insurance firms, etc.) and third-party data providers are invited to share existing best practices, common challenges, and areas of opportunity for cyber risk measurements with fellow practitioners, as well as computer scientists and economists with expertise in risk modeling. Our goal is to identify common approaches to data collection, relevant definitions, and risk measurements, along with computational techniques that enable necessary data insights while preserving sensitive, proprietary information. A second conference-style meeting will be held at a later date in mid-2022, bringing together a broader set of leaders from industry, academia, the Federal Reserve and other supervisory agencies to address key themes identified by Research Roundtable participants.