Small business insurance struggles to meet digital demands of owners

In recent discussions with industry leaders, it has been revealed that the small business insurance sector is experiencing significant challenges in adapting to the digital demands of small business owners. According to a report from Deloitte’s 2025 Insurance Industry Outlook, over 60% of small business owners prioritize digital experiences when choosing their insurance providers. However, these same owners feel that the insurance sector has fallen behind in terms of convenience, transparency, and personalization. Insurers are responding by streamlining offerings and enhancing service automation, with an eager focus on addressing this gap known as the 'employee confusion gap,' which refers to the disconnect between the benefits offered and employees’ understanding of them. To gain insight into these innovations, industry experts Bradd Chignoli from MetLife and Ben Rubin from Wintrust Financial Corporation shared their perspectives on the necessary changes within the industry. Chignoli emphasized the importance of fast onboarding processes for new plans, especially as many small employers lack the resources to manage complex benefits for their workers effectively. He stated that over 90% of new plans are implemented within a week, underscoring the need for efficiency in the onboarding process. Meanwhile, Rubin discussed the role of technology in significantly enhancing operational efficiency, noting the benefits of automating back-end processes that are time-consuming and often create bottlenecks in underwriting and approvals. He highlighted the integration of premium finance agreements with agency management systems, allowing brokers to streamline policy binding with ease. As medical and insurance costs rise, small employers are seeking creative solutions to manage expenses while maintaining adequate coverage for their employees. Utilizing voluntary benefits has proven to be a beneficial strategy, as it can enhance employees' perception of their benefits package, even when employers shift more financial responsibility onto their employees. Both leaders agreed that embracing technology is not just beneficial but essential to staying competitive. They contend that the small business insurance sector, despite complex challenges, is gradually becoming more accessible and efficient. Chignoli and Rubin's insights underscore that innovation is possible in a mature market, provided companies focus on solving real issues that affect their customers directly.