Colorado Springs, CO

Gary Whitsett

Executive Advisor for Leaders Managing Risk, Security, and Change

I work directly with CEOs and leadership teams when decisions carry real consequence.

How I think

Most organizations don’t fail because they lack tools or effort — they fail because decisions are made without enough context, structure, or accountability. Over time, I’ve learned that clarity matters more than speed, and judgment matters more than activity.

I approach security, compliance, and emerging technology as leadership problems first — and technical ones second. That means understanding risk in business terms, aligning priorities at the executive level, and ensuring responsibility is clear before execution begins. When decisions are treated as purely operational, organizations end up reacting instead of leading.

My work is guided by a set of principles: assess reality honestly, decide deliberately, and act in ways that can be sustained. I’m less interested in perfect answers than I am in sound decisions that hold up under pressure — especially when the margin for error is small.

The principles that guide my work:

Decisions before tools
Clarity before execution
Accountability over activity

Experience

Over the course of my work, I’ve advised leadership teams operating in environments where security, compliance, and technology decisions carry real organizational risk. Much of that work has involved helping executives navigate uncertainty — audits, regulatory pressure, incidents, and strategic change — while maintaining operational stability and forward momentum.

I’ve been accountable for translating complex technical and regulatory requirements into decisions leaders can stand behind. That means framing risk in business terms, clarifying ownership, and ensuring priorities are aligned before execution begins. In practice, this often involves stepping into moments where clarity is missing and consequences are

real.

My experience has reinforced a consistent pattern: organizations perform best when leadership maintains visibility and accountability over critical decisions, rather than delegating them entirely to tools, vendors, or siloed teams. My role has been to support that leadership posture — especially when the pressure is high and the margin for error is small.

Why I Built Bees

I built Bees after spending years watching capable organizations struggle with the same pattern: important decisions were being made in isolation, without enough context, structure, or ownership. Leaders were expected to move quickly, manage risk, and adopt new technology — often without the clarity or support needed to do so confidently.

I wanted to create a firm that operates differently. One that helps leadership teams slow down just enough to understand what actually matters, decide deliberately, and move forward with confidence. Bees exists to bring structure, discipline, and judgment to decisions that carry real consequence — especially in areas where security, compliance, and technology intersect.

At its core, Bees reflects how I believe this work should be done: advisory-first, grounded in reality, and accountable to outcomes. Not driven by tools, trends, or predefined solutions — but by the responsibility leaders carry and the environments they operate in.

How I Engage

I engage as a thought partner to leadership — working alongside CEOs and executive teams to bring clarity, structure, and perspective to decisions that matter. My role is not to replace internal teams or dictate outcomes, but to help leaders see risk clearly, align priorities, and move forward with confidence.

I work best in environments where open discussion, shared accountability, and disciplined decision-making are valued. That often means asking difficult questions, slowing conversations down when needed, and helping leadership teams navigate trade-offs rather than defaulting to quick fixes.

Engagements are shaped around the realities leaders face: organizational maturity, risk tolerance, and operational constraints. Whether the work involves advisory oversight, fractional leadership, or targeted support, my focus remains the same — improving the quality of decisions and the confidence with which they’re made.