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Holly Caldwell

Vice President
Voya Financial

Holly Caldwell is a digital and customer experience executive with over 20 years of business to business and business to consumer experience in the financial services industry. Holly currently leads the Digital Product Management team at Voya Financial, where she is responsible for the strategic direction, vision and customer experience across Voya’s digital properties. Holly and her team work with Voya’s customers, partners and leadership to define digital product solutions and priorities that meet the unique needs of their employee, employer and intermediary markets. Prior to joining Voya in 2018, Holly was a Senior Director at TIAA, where she developed strategies and solutions for the web, mobile and emerging channels serving their individual customers. Holly also spent 7 years at Fidelity Investments. As Senior Vice President, Advice and Guidance Product, she was responsible for the delivery of an integrated digital retail, workplace and intermediary retirement and financial planning offering. During that time, she led the development of the award winning “myPlan” product and was selected as one of twelve Fidelity executives to develop the firm’s 5-year business plan.


Holly’s career as a business leader in digital innovation and transformation began during the first dotcom boom in her role as Partner with the global consulting firm USWeb/CKS. With her focus on the creation of business value through digital communications and strategies, task number one at the time was convincing the C-suite that the internet was not just a fad. Her client work spanned Fortune 500 and start-up firms, and demanded her strategic, creative thinking as the world and business models were changing in profound ways. Throughout her career, Holly has maintained her intense focus on the customer and how their lives and experiences can be improved through compelling digital interactions.


Holly has a BS in Aeronautical Engineering from the United States Air Force Academy, and attended both the Babson School and Kellogg School of Management’s Executive Education programs. She lives on the coast of Connecticut with her husband and two rowdy golden retrievers. 

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