Westfield Promotes Tonya Ray Bailey to Head of Sales in Small Business
She will support the segment’s strategic growth by leading sales initiatives, strengthening agency relationships, and fostering a high-performing sales culture.
Bailey will work closely with Westfield Distribution, Product, and Underwriting teams to execute go-to-market strategies, increase agency engagement, and drive profitable portfolio growth through disciplined planning, analytics, and sales execution. Bailey has been with Westfield since June of 2022, most recently serving as Sales Lead for Small Business. She has more than 20 years of experience in the insurance industry, with a background that includes claims, underwriting, and sales.
Prior to joining Westfield, Bailey held progressive leadership roles with Nationwide, Harden, and Kemper Personal Insurance. Most recently, she served as Assistant Vice President of Strategy and Sales Execution in Personal Insurance with Kemper where she helped lead their national sales strategy and built a collaborative cross-functional sales and distribution team.
“Strong performance starts with clear priorities and alignment,” said Bailey. “My focus in this role is on creating clarity for our sales teams, deepening agency relationships, and establishing consistent execution that supports mutually beneficial long-term, sustainable, profitable growth.”
Bailey will report directly to Westfield’s Head of Small Business, Andy Rose, who has worked closely with Bailey during her tenure at Westfield. “Tonya Ray has consistently demonstrated strategic leadership and brings deep expertise and trusted relationships to this role. She is focused on strengthening Westfield’s value proposition for independent agents by making it easier to do business with us, aligning on shared goals, and helping agents grow their businesses and serve their clients more effectively.”
About Westfield
Founded in 1848, Westfield is a global leader in property and casualty insurance, delivering superior risk insights and innovative solutions to customers through a portfolio of insurance products. Westfield underwrites commercial, personal, surety and specialty lines of coverage through a network of leading independent agents and brokers in the United States and specialty products through Lloyd's of London Syndicate 1200. As a mutual insurance company with a workforce of more than 4,000, Westfield has revenues in excess of $4 billion and more than $11 billion in assets. Learn more at www.westfieldinsurance.com.