About Me

About Me

Hi, I’m Jess Sims

I began my career as an Executive Assistant, moved into the PMO, and went on to lead complex Workday and enterprise digital transformation programs for large organizations. That progression gave me a rare vantage point—from day-to-day operations to executive decision-making. Along the way, I saw the same pattern repeat itself: capable teams and well-intentioned leaders derailed by avoidable “gotchas”—misaligned stakeholders, unclear scope and SOWs, weak governance, and technology decisions disconnected from business strategy.

Jessica Sims

Mission - Helping leaders turn complex digital change into clear, achievable outcomes.

My mission is to help leaders and organizations navigate digital transformation with clarity, confidence, and purpose—by turning hard-won lessons into practical strategies that reduce risk, align stakeholders, and drive real business outcomes.

Vision - A world where digital transformation works the way leaders expect it to.

I envision a future where digital transformation is no longer defined by chaos, rework, or missed expectations—but by aligned teams, trusted data, empowered users, and technology that truly enables the business.