From E-1 Airman to Major: Why the Journey Matters for CFO Work Working your way up changes how you lead

Published: February 18, 2026 | By Gabriel Denny

I didn't commission as an Air Force officer.

I enlisted as an E-1—the lowest rank in the military. For three years, I worked on aircraft, took orders, did the grunt work that keeps the mission moving.

Then I went to Officer Training School, commissioned as a Finance Officer, and worked my way to Major and Squadron Commander—leading 140 people and serving as CFO for a nuclear missile wing.

That journey—from bottom to top—taught me more about leadership than any MBA program could.

Here's why it matters for CFO work.

You Learn What Actually Matters

When you're an E-1, you see the difference between leaders who talk about values and leaders who live them.

You see which policies make sense and which are bureaucratic garbage that wastes everyone's time.

You learn which leaders earn respect and which demand it (and fail).

The business lesson: If you've never done the work your team does, you don't really understand the problems you're asking them to solve.

The best CFOs have been in the trenches. They know what's hard, what's tedious, and what's broken.

You Understand What Motivates People

As an enlisted airman, I didn't care about the Wing Commander's strategic vision.

I cared about:

Does my supervisor have my back?
Am I learning skills that matter?
Do I feel valued or like a cog in a machine?
Can I see a path forward?

Those questions don't change when you become an officer or a CFO. People want to feel valued, challenged, and supported—regardless of rank or title.

The business lesson: Most executives think comp and titles motivate people. They don't. Purpose, growth, and respect do.

If you've been at the bottom, you remember what actually mattered.

You Earn Credibility the Hard Way

When I commissioned as an officer, I didn't magically become a better leader.

But I had something most new lieutenants didn't: credibility with enlisted troops.

They knew I'd done their job. I understood their challenges. I wasn't some college kid fresh out of ROTC telling them how things should work.

That credibility mattered. When I gave direction, they trusted I understood what I was asking them to do.

The business lesson: Leaders who've never done the hard work struggle to earn respect.

You can demand compliance, but you can't demand trust. Trust is earned—usually by proving you've walked the path your team is walking.

You See Both Sides of Every Decision

As a commander and CFO at Malmstrom, I made decisions that affected hundreds of people. Budget cuts, reorganizations, policy changes.

But because I'd been on the receiving end of those decisions as an enlisted airman, I understood their impact differently.

I knew what it felt like when leadership made changes without explaining why. I knew how frustrating vague direction was. I knew when a policy sounded good on paper but would fail in execution.

So when I made decisions, I communicated clearly. I explained the "why." I anticipated pushback because I'd been the one pushing back years earlier.

The business lesson: Leaders who've only been at the top make tone-deaf decisions.

They don't understand how their choices ripple through the organization. Ground-up leaders do.

You Learn Humility (The Hard Way)

When you start at the bottom, you fail. A lot.

You make mistakes, get corrected, and learn humility.

I've screwed up aircraft maintenance. I've been chewed out by senior enlisted leaders. I've had to apologize for errors and fix them.

That shapes you. It teaches you that rank doesn't make you infallible. It teaches you to admit mistakes, learn fast, and move forward.

Contrast that with leaders who've never failed publicly. They double down on bad decisions because admitting error feels like weakness.

The business lesson: The best leaders I know have failed spectacularly at some point. It made them better.

Leaders who've never struggled often crack under real pressure.

You Build a Deeper Network

Because I came up through enlisted ranks, I built relationships across the entire organization—not just with officers.

When I needed something done as a commander, I knew who the key people were. I knew which senior enlisted leaders ran the real show. I knew how to navigate the system.

Leaders who only know other executives miss 80% of what's actually happening in their organizations.

The business lesson: The people closest to the work know where the problems are.

If you only talk to VPs, you're getting a filtered version of reality. Ground-up leaders know who to talk to for truth.

You Appreciate Opportunity

When you start as an E-1, getting promoted to E-2 feels like an achievement. Becoming an NCO is huge. Commissioning as an officer feels impossible.

Every step up, you appreciate it. You don't take it for granted.

Leaders who started at the top often don't realize how fortunate they are. They expect opportunities. They feel entitled to advancement.

Ground-up leaders know better. We earned everything. We don't expect handouts.

The business lesson: Gratitude and humility make better leaders than entitlement and ego.

How This Applies to CFO Work

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

But have they:

Done manual data entry and reconciliation?
Dealt with frustrating accounting software?
Struggled with unclear direction from leadership?
Felt undervalued despite working hard?

If not, they don't fully understand the challenges their finance teams face.

Ground-up CFOs do. We've been there. We know what's broken because we've lived it.

The Bottom Line

Working your way up from the bottom isn't just a nice backstory.

It fundamentally changes how you lead:

You understand what actually matters to your team
You earn credibility through experience, not title
You see both sides of every decision
You lead with humility instead of ego
You build deeper networks across all levels
You appreciate every opportunity

At Malmstrom AFB, my enlisted background made me a better commander. In fractional CFO work, it makes me a better leader.

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

And that perspective is irreplaceable.

Want a CFO who understands your team's challenges from experience?

Schedule a Financial Health Assessment and see how ground-up leadership makes a difference.

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About Gabriel Denny

Started as E-1 Airman. Retired as Major and Squadron Commander. The journey taught me everything about leadership.