Laura Olson

About the Author

Laura Taccini Olson is the Chief Insurance Officer at Obie, where she leads the company's insurance strategy, overseeing product development, underwriting, actuarial, claims strategy, compliance, customer experience, and insurance operations. As a member of the executive leadership team, she is responsible for building scalable insurance solutions that enable real estate investors to protect and grow their portfolios with confidence. With more than two decades of experience spanning carriers, reinsurers, and InsurTech, Laura has built a reputation for transforming complex insurance organizations into high-performing, technology-enabled businesses. Prior to joining Obie, she held senior leadership roles at CSAA Insurance Group, Esurance, Munich Re, and Homesite Insurance, where she led initiatives across product management, business development, operations, underwriting, and strategic partnerships. This breadth of experience provides her with a unique perspective across the entire insurance value chain—from risk selection and pricing to distribution, technology, and customer experience. Since joining Obie, Laura has played a pivotal role in scaling the company's insurance platform, expanding its product portfolio, strengthening underwriting capabilities, and developing innovative solutions tailored to the evolving needs of real estate investors. She has helped build a modern insurance organization that combines data-driven underwriting, proprietary technology, and disciplined risk management to deliver exceptional customer outcomes while supporting rapid business growth. Laura is passionate about modernizing the insurance industry through thoughtful innovation, operational excellence, and cross-functional leadership. She is recognized for her ability to bridge business strategy with technology, align diverse stakeholders around ambitious goals, and build teams that consistently deliver market-leading results.