Cindy Gross (she/her) is an executive coach, facilitator, and leadership systems strategist with 25+ years of experience in complex technology organizations, including 18 years at Microsoft across engineering, cloud architecture, and culture leadership. She brings a rare combination of deep technical fluency and human-centered coaching to her work —helping leaders and teams navigate volatile, matrixed environments with greater clarity, confidence, and impact.
In technology modernization engagements, Cindy bridges the gap between technical systems and human systems. She supports organizations in diagnosing and reducing systemic friction, building leadership capacity during transitions, and developing the organizational velocity needed to sustain change. Her coaching and facilitation work is grounded in Adaptive Leadership, Systems Thinking, and the Leadership Circle Profile (LCP) 360 — an evidence-based assessment that surfaces what leaders and organizations often can't see on their own.
Cindy is an ICF Professional Certified Coach (PCC),a Certified Gracious Space Facilitator, and a certified practitioner of the Leadership Circle Profile 360. Her facilitation approach draws on Gracious Space, anti-oppressive frameworks, and equity-centered design — creating environments where diverse voices are heard and teams can do their most honest,generative work together. As a citizen of the Cherokee Nation and Delaware Tribe of Indians, she brings an Indigenous perspective to collective leadership and systems change, grounded in the concept of Gadugi — community coming together in shared purpose.
Cindy's work spans public sector technology modernization, leadership development, and organizational health. She is committed to building leadership infrastructure that holds — not just during periods of stability, but especially under pressure.
