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
Gabriel Denny Financial Services, LLC