Partner

Connor Cosgrove leads Digital Transformation at Cosgrove Partners, helping executive teams modernize how their organizations run — across data infrastructure, AI and automation, and technology strategy. He operates at the intersection of finance, technology, and operations, serving as an embedded technology leader and strategic partner who augments internal capabilities to support value creation initiatives and integrations.

His work spans the full transformation stack: designing modern data warehousing and analytics platforms that consolidate disparate business systems into a single source of truth; building AI-powered tools and automation that eliminate manual work and unlock new capabilities; and advising on the technology strategy, ERP architecture, and system integrations that let growing companies scale without breaking. Connor's engagements range from board-level advisory to dashboards and KPI scorecards to custom internal AI applications — always with an eye toward turning technology into a durable, actionable asset.

With 10+ years of experience spanning software engineering, data analytics, and financial strategy, Connor brings a unique blend of technical and business expertise. Prior to joining Cosgrove Partners, he worked as a full-stack product engineer in both the private and public sectors and led client success initiatives focused on retention, satisfaction, and product expansion.

Connor studied Informatics, Finance, and History at Indiana University. Outside of work, he’s an avid golfer and lifelong fan of IU athletics, the Colts, and Liverpool FC.