Cybersecurity has become less of a technical operation and more of the main element of organizational resilience. Although massive investments in the world have been made, most organizations are still susceptible because of disjointed strategies and insufficient attention to human and procedural factors. This paper presents a quantitative, decision-based, cyber insurance framework that overcomes the limitations of the existing models such as lack of past data and ambiguity of its coverage by a risk assessment framework of 12 parameters of organizational, regulatory and technological aspects. The framework was verified on a synthetic data containing 500,000 organizational profiles and an interactive Dash-Plotly dashboard, which allows visualizing cyber risk scores in real-time. This strategy enables firms to recognize the points of vulnerability, evaluate cyber maturity, and make informed insurance decisions by combining human, process, and technological dimensions and helping insurers to make accurate underwriting choices. The model facilitates data-oriented, scalable and responsive cyber resilience, adjusting the management of security systems to risk transfer policies.