Cindy Chastain is an award-winning design and transformation executive with more than two decades of experience helping global organizations turn customer insight and ambitious strategy into customer-centered growth.

During a decade at Mastercard, most recently as SVP and Global Head of Customer Experience & Design, Cindy led enterprise transformation work spanning customer experience, brand identity, digital platforms, and the company’s product operating model. Over her tenure, she built experience design into a strategic business capability that improved product adoption, sales growth, and revenue. She also helped shape the product strategy and design of more than 40 new-product initiatives within an innovation portfolio representing $800 million in potential revenue. Her work was recognized with two Mastercard CEO Awards, honoring team contributions to the company’s brand identity relaunch and its first GenAI productivity tool for frontline implementation specialists.

Before Mastercard, Cindy was a customer experience strategy and design leader in R/GA’s Business Transformation group. There, she partnered with Nike on a three-year transformation of its B2B go-to-market platform. She helped define the future-state ambition, connect capability needs to customer value, design an ecosystem of eleven integrated applications, and establish a new operating model to sustain the transformation. The program generated more than $500 million in incremental revenue during its first eighteen months. Her clients also included Volvo, Verizon, and Walmart.

Today, through Indelible Design, Cindy advises executive leaders on organizational adaptation in the age of AI. She is known for bringing clarity to complex transformation challenges and turning that clarity into aligned leadership decisions and pragmatic paths to action—while keeping human judgment and customer value at the center.