I help organizations turn messy, high-stakes change—like Workday and enterprise technology rollouts—into clear, governed, and human-centered transformations.
“From Executive Assistant to leading large-scale ERP programs, I’ve sat in the seats of stakeholders, PMOs, and executives—and I built The Gotcha Guide so you don’t have to learn everything the hard way.”
I started my career as an Executive Assistant, moved into the PMO, and eventually led complex Workday and digital transformation programs for large organizations. Along the way, I kept seeing the same pattern: smart teams derailed by avoidable “gotchas”—misaligned stakeholders, fuzzy SOWs, weak governance, and tools chosen for the wrong reasons.
The Gotcha Guide is my way of saying: I’ve been there. I gotcha covered.
On this site, you’ll find the frameworks, checklists, and stories I wish I’d had from day one.
I support leaders and teams at critical moments in their transformation—bringing clarity, structure, and momentum when it matters most.
The mission of The Gotcha Guide is to demystify digital transformation by
exposing the “gotchas” that derail well-intentioned initiatives—and replacing them with practical plays leaders can run on purpose.
The Gotcha Guide envisions a generation of leaders who don’t have to learn digital transformation the hard way—because they have access to real stories, proven frameworks, and tools built from experience, not theory.
Mar , 2026
March 30 – April 3
The Gotcha Guide Podcast — Micro-learning in 15 minutes
“Jess brought calm, confident leadership to a complex program with a large, cross-functional team.”
“Clarity around business processes made all the difference.”
“This is the best Workday implementation I’ve ever experienced.”