Erin Fleckenstein Joins Goodwill Greater Milwaukee & Chicago As Senior Vice President, Information Technology
Goodwill Greater Milwaukee & Chicago today named Erin Fleckenstein, senior vice president, information technology, effective September 2, 2025.
Fleckenstein has more than two decades of experience leading digital transformation in complex, highly regulated environments, aligning technology strategy with core business objectives. She has extensive expertise delivering scalable solutions that drive operational efficiency, enhance customer experience, and accelerate enterprise growth for companies including ADUSA and The Options Clearing Corporation.
“Erin’s experience designing and implementing sophisticated technical solutions across in-store, mobile and online platforms to support large-scale e-commerce, retail, media and marketing initiatives will help us build and scale our technology investments as we grow our businesses and expand our mission impact,” said Jeff Docalavich, chief financial and administrative officer for Goodwill Greater Milwaukee & Chicago. At Goodwill, she’ll use that experience to advance the organization’s mission - Connecting people to work. Preparing people for life. - while driving business growth throughout the social enterprise. Erin will lead the strategic direction, innovation and operational excellence of the organization’s technology team, ensuring that its IT systems and solutions effectively support business goals and drive digital transformation.
“I am honored to be joining the talented team at Goodwill Greater Milwaukee & Chicago,” Fleckenstein shared. “The mission of connecting people to work and preparing people for life is inspiring, and I am excited to have the opportunity to contribute to its advancement. I look forward to collaborating with the technology team to deliver innovative solutions that enhance the experience of our customers and make a lasting impact in the communities we serve.”
At the forefront of the organization’s strategic priorities, Goodwill is focused on providing exceptional shopping and donating experiences which fuel its community impact across greater Milwaukee and Chicago.