The insurance industry is heavily dependent on several processes executed among multiple entities, such as insurer, insured, and third-party services. The increasingly competitive environment is pushing insurance companies to use advanced technologies to address multiple challenges, namely lack of trust, lack of transparency, and economic instability. To this end, blockchain is used as an emerging technology that enables transparent and secure data storage and transmission. In this paper, we propose CioSy, a collaborative blockchain-based insurance system for monitoring and processing the insurance transactions. To the best of our knowledge, the existing approaches do not consider collaborative insurance to achieve an automated, transparent, and tamper-proof solution. CioSy aims at automating the insurance policy processing, claim handling, and payment using smart contracts. For validation purposes, an experimental prototype is developed on Ethereum blockchain. Our experimental results show that the proposed approach is both feasible and economical in terms of time and cost.