About Gabriel Denny

From Airman to CFO: A 20-Year Journey in Military Finance Leadership

The Beginning: E-1 Airman

I didn't start my Air Force career as an officer. I started at the bottom—enlisted as an E-1, the lowest rank in the military.

For three years, I worked on aircraft as an Airfield Systems Craftsman. I took orders, did the grunt work, and learned what it meant to be part of a team where everyone's contribution mattered.

That experience taught me something most executives never learn: what it's actually like to work your way up.

The Pivot: From Enlisted to Officer

I worked my way up to E-5 (Staff Sergeant), then made a decision that changed everything: I applied to Officer Training School.

I was accepted, commissioned as a Finance Officer, and began a new chapter—this time as a leader, not just a team member.

But the years I spent as an enlisted airman gave me credibility that most new lieutenants didn't have. I understood what I was asking my teams to do because I'd done it myself.

Combat Finance: $33 Billion in High-Stakes Operations

In 2014, I deployed to the Middle East as the CFO for all special operations aircraft operations (excluding Afghanistan) during ISIL operations.

My mission? Manage financial operations for combat missions worth over $33 billion.

This wasn't boardroom finance. This was:

  • Making funding decisions when missions launched within hours
  • Managing complex financial operations in a combat-adjacent environment
  • Performing the first combat zone audit in five years and finding $2M in reallocatable funds
  • Building systems that worked under pressure—because failure had consequences beyond the P&L

That deployment taught me what real risk management looks like: not theoretical models, but actual decisions with actual stakes.

Squadron Commander & CFO: Malmstrom AFB

In June 2020, I took command of the 341st Comptroller Squadron at Malmstrom Air Force Base—CFO for America's largest nuclear ICBM wing.

The scope:

  • 140 personnel under my command across financial, legal, audit, and public affairs disciplines
  • $125M annual budget execution
  • $372M economic impact to the state of Montana
  • $235M in pay operations for over 8,500 active duty, dependents, and retirees

Key Achievements at Malmstrom:

1. Zero Base Review → $2.4M in Savings

Led the wing's first-ever Zero Base Review, engaging 37 commanders and directors. Identified $2.4M in savings, defended an $80M budget and secured a $12M increase, and built a $130M FY21 budget from the ground up.

2. COVID-19 Leadership → #1 Global Ranking

Took command in June 2020—right in the middle of the pandemic. Led 140 people through crisis while maintaining nuclear deterrence operations. Result: #1 global ranking in our career field within the first year.

3. Process Optimization → 80% Time Reduction

Overhauled financial processes, reducing production time by 80% while cutting labor costs by $5M and increasing organizational effectiveness.

4. Team Development → 11 Major Awards

My team earned 11 AFGSC/FM and wing/group quarterly awards, multiple Below-the-Zone promotions, and OTS selections—proving that taking care of your people drives results.

Military Awards & Recognition

  • Defense Meritorious Service Medal - Awarded for exceptional service in combat operations
  • Meritorious Service Medal (3x) - Multiple awards for outstanding leadership
  • Joint Service Commendation Medal - For joint operations excellence
  • Air Force Commendation Medal (3x) - For superior performance
  • Inherent Resolve Campaign Medal - Middle East combat operations
  • DoD Comptroller of the Year (#1 out of 1,200 finance officers)
  • Field Grade Officer of the Year (#1 out of 240 officers)
  • Space Command Company Grade Officer of the Year (#1 out of 200 officers)
  • Sijan Award Nominee - Air Force's highest honor for junior officers

Transition to Corporate Finance

After retiring in 2022, I transitioned to the private sector—bringing military discipline to growing businesses:

Chief Financial Officer - Entech (PE-Backed MSP)

December 2024 - October 2025

  • Led $29M/year managed service provider through PE transition
  • Facilitated two acquisitions, driving $9M in growth during first year
  • Revamped customer contract structure, increasing total contract value and staging company for exit
  • Managed Business Operations and Accounting teams, led executive team

Director, Finance & Business Analytics - ARCOS LLC (Vista Equity-Backed SaaS)

January 2024 - December 2024

  • Built unified business data lake using AWS, PowerBI, and OpenAI API
  • Contracted Procurement-as-a-Service provider, driving $158K in first-year savings
  • Integrated advanced AI capabilities into account database for TAM insights
  • Enabled largest single customer sale in company history through data-driven insights

I have also sat in the finance seat for two early-stage tech companies raising on SAFEs and first priced rounds.

Education & Certifications

  • Master's Degree, Accounting & Financial Management - University of Maryland Global Campus
  • Bachelor's Degree, Business Administration - University of Phoenix
  • USAF Air Command and Staff College - Military and Strategic Leadership
  • Project Management Professional (PMP) - Project Management Institute
  • Certified Defense Financial Manager (CDFM) - Military equivalent of CFA
  • Defense Acquisition Workforce Improvement Act (DAWIA) Certifications

Why I Do This

Most fractional CFOs come from Big 4 firms or corporate finance roles. That's fine—but it's not the same as managing billions in combat zones or leading financial operations for nuclear deterrence.

I bring a different level of experience:

  • Decision-making under pressure - When your quarterly close feels stressful, remember: I've made financial decisions when lives were on the line.
  • Ground-up leadership - I started as E-1 and earned every promotion. I know what it's like to work your way up.
  • Crisis management - I took command during COVID and achieved #1 global ranking. Your business challenges are real—but they're solvable.
  • Systems that work under stress - I've built financial operations that function in chaos. If your business feels chaotic, I've worked in worse.

That's what I bring to your business. Not theory. Not consultants' "best practices." Real experience delivering results when it actually matters.


Ready to work with a CFO who's been tested under fire?

Book 30 minutes or call (616) 881-6777.

Quick Facts

  • Military Service: 20 years (2002-2022)
  • Final Rank: Major (O-4)
  • Started as: E-1 (Airman Basic)
  • Combat Deployments: Middle East operations
  • Largest Command: 140 personnel
  • Largest Budget: $720M annual
  • Funds Managed: $33B+ in combat ops

Core Competencies

  • Zero-Based Budgeting
  • M&A Due Diligence & Integration
  • FP&A & Strategic Planning
  • Crisis Leadership
  • Risk Management
  • Process Optimization
  • Team Development
  • Audit & Compliance
  • ERP Implementation (NetSuite, Sage, Salesforce)
  • AI-Driven Analytics

Let's Connect

Want to discuss how military-grade financial leadership can help your business scale?

Phone: (616) 881-6777

Email: gabe@gabrieldenny.com

Book 30 minutes