Josh Jewett

Operating Executive at UPSTACK

Speaker

Josh is an Operating Partner at UPSTACK, bringing decades of leadership experience as a technology executive and veteran CIO. He has served as CIO for two large retail enterprises—Family Dollar and Dollar Tree—where he led transformative IT initiatives, modernized enterprise systems, and enabled new business models.

Earlier in his career, Josh co-founded and grew a retail technology consulting firm, later acquired by a national consultancy. His expertise spans IT strategy, operational performance improvement, and enabling business growth through advanced technology solutions.

Josh earned a B.A. from Dartmouth College and has been recognized as CIO of the Year by both RIS News and the Charlotte Business Journal.