Conor Healy built IAB's IT function from the ground up after inheriting a failed Salesforce implementation and a leadership team that had already been burned. He explains how he used a 30/60/90 framework to earn trust without rubbing anyone's face in what had gone wrong, and why getting leadership to feel like co-owners of a solution is the actual work of building credibility in a role with no track record.

A nine-year CIO explains how credit unions accumulate operational debt by launching products and processes with "just make it work" as the plan. The manual handoffs, duplicate data entry, and uncoordinated workflows quietly compound until the organization can't scale or adopt automation.

José Manuel Rodríguez Jiménez, CIO at Metro in Portland, Oregon, explains why AI efficiency claims fall flat without a plan for the reclaimed hours. Drawing on 25 years of IT leadership across two continents, he describes how building relationships at every level of the organization, starting with frustrations rather than requirements, creates the foundation for shared ownership of technology decisions.

Chuck Scharnagle, CIO at Revere Copper Products, describes how he rebuilt credibility at the oldest continuous manufacturer in the United States by delivering incrementally, speaking in business outcomes, and treating IT as a customer service organization. His approach turned a department that executives openly resented into one they no longer question.