I’m Diana Lee — a strategist, systems thinker, educator, and founder working at the intersection of AI adoption, operational modernization, communication, and human behavior.
My background spans healthcare, software engineering, systems design, branding, operations, entrepreneurship, and AI implementation. At one point those experiences felt disconnected. Now they feel like different ways of studying the same thing:
how humans operate inside systems.
I founded Waggle.ai during the rise of generative AI after leaving my 9–5 in 2023 — stepping directly into one of the biggest technological shifts of our time alongside everyone else trying to make sense of it in real time.
A lot of what I’ve done over the last several years has been less about “teaching AI” and more about observing people inside transition.
§ Observed
- How humans respond under pressure.
- How teams communicate.
- How leadership adapts.
- How people learn.
- How they resist.
- How they burn out.
- How they rebuild.
- How systems either support people — or quietly overwhelm them.
I’ve now worked with thousands of people globally across different stages of AI readiness — from people opening ChatGPT for the first time to organizations trying to understand what modernization actually looks like operationally.
And underneath most of it was the same thing:
people overloaded, communication fragmented, systems disconnected, and teams trying to adapt while still keeping everything moving.
That’s the layer of the work I care most about.
Not automation for automation’s sake.
Not chasing trends.
Not removing humanity from work.
I care about helping people modernize in ways that are practical, sustainable, and human.
§ Background
- Healthcare & pharmacy operations
- Software engineering & government technology
- Systems & workflow design
- Branding & digital ecosystems
- Entrepreneurship & operations
- AI education, implementation & adoption
§ A maternal lens
A huge part of this perspective comes from being a mother.
When you look at technology through a maternal lens, you stop asking only:
“What can this do?”
You start asking:
- What is this doing to people?
- How are humans experiencing this?
- What kind of environments are we creating?
- What happens to communication, trust, attention, learning, confidence, and identity inside rapidly changing systems?
That lens shapes everything I do.
It’s why I care deeply about clarity. About operational sustainability. About reducing overwhelm instead of adding to it. About helping people think more clearly instead of faster. About building systems that support humans rather than quietly fragmenting them.
Technology may move fast.
Humans still have to live inside the systems we build.
And I think that deserves far more thought, care, and responsibility than most conversations around AI currently allow.