San Mateo, California, United States, August 2025 – Kelly Whiteside has been appointed as Chief People Officer at California Casualty, where she will lead the company’s people strategy, overseeing talent acquisition, employee engagement, organisational development, leadership capability building, DEI initiatives, and total rewards. Her role will be pivotal in supporting California Casualty’s mission of providing protection and peace of mind for those who serve our communities.
Whiteside most recently spent over seven years with Afiniti, where she held multiple leadership positions including Senior Vice President, Global Human Resources; Global Head of Culture and People Development; and Vice President, Client Services. In these roles, she led global people operations, talent and performance management, DEI and belonging, people development, and benefits strategy, while also overseeing large client service operations. She played a central role in shaping a high-performance culture and aligning people strategies with business growth objectives.
Previously, she was Principal, Service and Operations Transformation at The Montage Group, where she partnered with organisations across industries to improve customer experience and operational efficiency. Her work included reducing conversion times by more than 80%, increasing customer retention to over 94%, and implementing innovative process improvements to deliver world-class experiences.
Earlier in her career, Whiteside spent over 13 years at T-Mobile, where she held senior leadership positions including Vice President, Service Transformation; Vice President, Operations and Sales Enablement; Director and General Manager, Bellingham Call Center; and General Manager, Frisco Call Center. She led large-scale organisational transformations, built and launched new operational hubs, implemented digital-first customer experience strategies, and drove award-winning service improvements recognised by J.D. Power.
She began her career with Verizon Enterprise Solutions as Regional Senior Manager, B2B, where she oversaw customer service operations for a $10M annual base and earned top performance recognition.
About California Casualty
Founded in 1914, California Casualty is dedicated to providing high-quality insurance coverage at competitive prices to those who serve our communities, including educators, law enforcement, and public safety professionals. The company offers tailored benefits such as deductible waivers for educators’ vehicles damaged at school and premium waivers for survivors of public safety officers lost in the line of duty. California Casualty also actively supports community causes, from heart disease and cancer research to environmental sustainability through digital service options.
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