Against a backdrop of escalating global competition, health insurance firms grapple with the need to stand out amidst a saturated market. The study recognizes the imperative for organizations to adopt differentiation strategies, with a focus on product, personnel, distribution, and image differentiation. Acknowledging the current dearth of comprehensive research in the Kenyan context, the research problem centres on the critical need to investigate the extent to which differentiation strategies influence the performance of health insurance companies in the region. The general objective of the study was to investigate the effect of differentiation strategy on performance of Health Insurance Companies in Kenya. Drawing on established theories such as Porter's Competitive Advantage Model, Upper Echelons Theory, Resource-Based View, and Transaction Cost Economics, the study employs a multi-theoretical framework to provide a nuanced understanding of the complex relationships between differentiation strategies and organizational outcomes. Adopting the descriptive research design, the target population comprises 980 employees in the medical insurance firms in the top management and middle level management in Nairobi, drawn from the respective insurance firms’ Human Resources Departments. Employing a multi-stage sampling technique, the established sample size is 101 top and middle level management staff who were reached by stratified random sampling. A semi-structured questionnaire was the main data collection instrument and was distributed through a drop-and- pick- latter approach. Data was analyzed using both descriptive and inferential statistics. Descriptive statistics measures of mean and standard deviation was used, while for inferential statistics, regression equations were employed. The study established that product differentiation strategy, personnel differentiation strategy, product differentiation strategy and image differentiation strategy had a positive significant effect on performance of health insurance companies in Kenya. The study concludes that product differentiation is the key aspect distinguishing one company’s products or services from its competition. Personnel differentiation strategy gives an organization the ability to respond in time to the needs of their members through the skills and knowledge of employees. A differentiated distribution strategy allows insurance companies to expand their sale potential by getting their product in front of more potential customers. An effective image establishes the product's character and value proposition and a person responds differently to company and brand images. The study recommends that the insurance companies should consider opportunities for differentiation in all of its production areas: marketing, product management, engineering, sales, and customer support. Organizations looking to build personnel differentiation strategy will need to produce or design extremely unique or distinctive products or services that create increased value for the consumer. The insurance companies should devote resources to channel management preferably at least one dedicated manager whose sole responsibility is to manage those relationships and build the marketing programs to drive revenue through the channel. The insurance companies should identify their brand gaps, which are the discrepancies between their desired and actual brand performance.