This document describes Focal Point's cyber risk quantification services for insurance underwriting. It outlines a four-step roadmap for measuring an organization's cyber risk profile to inform insurance strategies. The first step leverages an organization's existing NIST Cybersecurity Framework assessment. The second step involves further evaluating cyber risks through an online self-assessment or deeper evaluation. The third step uses Monte Carlo modeling to measure potential cyber loss scenarios. The fourth step provides insights to define an appropriate risk strategy and optimize insurance coverage, limits, and deductibles. The document argues this approach helps organizations better understand cyber risks, prioritize mitigation options, and make informed decisions about cyber insurance.