Will Milewski is a seasoned technology executive with deep expertise in public cloud platforms, large‑scale SaaS operations, and enterprise modernization initiatives. He has held multiple senior leadership roles, including Vice President of Cloud Platform Operations at Benefitfocus and Vice President of Cloud Operations at PowerSteering Software. He is recognized as a proven leader for driving digital transformation, operational excellence, and the scaling of global infrastructure teams. As Senior Vice President of Technical Operations at Duck Creek Technologies, he leads cloud engineering, reliability, and platform modernization efforts that support the company’s global customer base.