Dennis D. Scott – My Story
I work on the hardest part of leadership: decision-making when it matters.
I’m Dennis D. Scott - a strategic leader, founder, and systems thinker shaped by service, disruption, and a lifelong focus on how humans operate inside complex systems.
How He Works
In 1996, I entered military service and served as a soldier in the 3rd U.S. Infantry Regiment (The Old Guard) - a unit defined by discipline, precision, and public trust. During that time, I was nominated to attend the United States Military Academy Preparatory School, and subsequently the United States Military Academy at West Point. Those years fundamentally shaped how I think about leadership, responsibility, and the weight of decisions when others depend on them.
That trajectory was interrupted by a medical discharge.
It was an unexpected transition - one that forced me to confront uncertainty early in life. But it also clarified something essential: my commitment was never to a uniform or a role. It was to service, judgment, and helping people perform at their best under pressure.
From Service to Systems
After leaving the Army, I began my civilian career as a human factors engineer, working inside complex environments where small design decisions could have outsized consequences. My focus wasn’t on tools - it was on how people interact with systems, how confusion is created, and how clarity can be designed.
From there, my career expanded into leadership roles with increasing responsibility, guiding initiatives that bridged people and technology to improve decision - making, execution, and experience - both internally within organizations and externally for those they serve.
Across healthcare, higher education, research institutions, and large enterprises, I saw the same pattern repeat:
Smart people. Capable teams. Powerful systems. And yet - misalignment, hesitation, poor decisions.
The result was predictable: slower execution, stalled initiatives, and outcomes that fell short - not because of effort, but because of how decisions were framed and owned.
The constraint was never intelligence or effort.
It was how decisions were framed, felt, and made.
Executive Leadership & Transformation
That insight carried me into senior leadership, including work as a Digital Transformation Leader at Microsoft, where I partnered directly with executives navigating modernization, large-scale change, and emerging technologies like AI.
My role was rarely about the technology itself. It was about helping leaders see clearly - how incentives, emotions, narratives, and systems intersect - and then design decisions that teams could actually execute.
My leadership style emphasizes clarity, accountability, and narrative alignment, because strategy only matters if people understand it well enough to act.
Founder: iExperience iLearn
Everything I’ve lived and observed ultimately converged into one question:
Why do we wait until adulthood - often after failure - to teach decision-making?
Most of us learned decision-making the hard way - through mistakes that were expensive, painful, or permanent. I believe children deserve a better path.
That question led me to found iExperience iLearn.
iExperience iLearn is an AI-powered emotional learning ecosystem that uses cinematic storytelling and adaptive intelligence to help learners experience decisions, consequences, and emotional signals in context. Instead of abstract instruction, learners build judgment through lived experience - safely, early, and intentionally.
The platform begins with children, because that’s where the gap starts. It is intentionally designed to scale across age groups and contexts - from families, to schools, to leaders and organizations - because the need for better decisions never goes away.
Foundation & Perspective
My work is grounded in a multidisciplinary foundation:
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United States Military Academy at West Point - B.S., Engineering Psychology
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University of Pennsylvania - M.S.E., Engineering (Wharton & Penn Engineering)
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University of Oxford, Saïd Business School - Executive MBA
This blend allows me to operate fluently across human behavior, systems design, and executive strategy - and to connect them into coherent, usable frameworks.
What Drives Me
At the core, I believe this:
The quality of our lives, organizations, and societies is determined by the quality of our decisions - and decision-making is a skill that can be developed.
My work is about building systems that make that development possible - clearly, responsibly, and at scale.
I don’t chase novelty.
I build for durability.
Join me
on my Journey
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In Short
Dennis D. Scott is a strategic leader, AI innovator, and founder focused on elevating human decision-making. With over two decades of experience across the military, enterprise technology, and executive leadership, he helps leaders and organizations navigate complexity with clarity and intent.
As the Founder of iExperience iLearn, Dennis is building an AI-powered emotional learning ecosystem that blends cinematic storytelling with adaptive intelligence to develop judgment, resilience, and emotional awareness. He holds degrees from West Point, Wharton/Penn Engineering, and Oxford Saïd, and works at the intersection of strategy, technology, and human potential.
My Core Identity
“I help people and organizations make better decisions by designing systems that align strategy, emotion, and intelligence.”