Published: November 1, 2025 | By Gabriel Denny

I didn't start as an officer. I started as an E-1 Airman—the lowest rank in the Air Force.

Three years working on aircraft. Taking orders. Doing grunt work.

Then Officer Training School. Finance Officer. Squadron Commander. CFO of a nuclear missile wing leading 140 people.

That journey taught me more about leadership than any MBA program could.

Why Starting at the Bottom Matters

When you've been on the receiving end of leadership decisions, you lead differently.

You remember what it felt like when:

• Leadership made changes without explaining why
• Your supervisor didn't have your back
• Policies sounded good on paper but failed in execution
• You felt like a number instead of a person

That perspective is irreplaceable.

What Working Your Way Up Teaches

1. Respect is Earned, Not Given

Commissioning as an officer didn't make me a better leader. But having enlisted experience gave me credibility with troops who knew I'd walked their path.

2. You Learn What Actually Matters

Enlisted troops don't care about strategic visions. They care about: Does my supervisor support me? Am I learning? Do I feel valued?

Those questions don't change when you become a CFO.

3. You See Both Sides

As a commander making budget cuts or policy changes, I understood their impact because I'd been on the receiving end. That made me a better communicator and decision-maker.

4. Humility Gets Baked In

When you start at the bottom, you fail. A lot. You learn humility the hard way—and that makes you better when you're in charge.

How This Applies to CFO Work

Most fractional CFOs come from corporate accounting roles. They understand spreadsheets and compliance.

But have they:

• Done the manual data entry their team does?
• Struggled with unclear direction from leadership?
• Felt undervalued despite working hard?

Ground-up leaders have. We know what's broken because we've lived it.

The Leadership Difference

Working your way up changes how you lead:

• You understand what motivates your team (purpose, growth, respect—not just comp)
• You earn credibility through experience, not title
• You see the ripple effects of your decisions
• You lead with humility instead of ego
• You build deeper networks across all levels

The Bottom Line

Starting as an E-1 Airman and rising to Major wasn't just a career path. It was leadership training that no classroom could replicate.

I remember what it's like to be on the other side of leadership decisions.

That perspective makes me a better CFO.

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About Gabriel Denny

E-1 Airman to Major and Squadron Commander. The journey taught me everything about leadership that matters.