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From Pilot to Defense Innovator: Forrest Underwood on Navigating the Future of Government Contracting
Forrest Underwood’s career is a story of serendipity, bold pivots, and an insider’s view of how defense innovation is reshaping the future of U.S. national security. What began with an unlikely conversation at a grocery store in high school evolved into a path that took him from flying special operations aircraft to helping shape how the Pentagon invests in emerging technology.
Today, Underwood serves as Chief of Joint Investment Strategies at the Office of the Secretary of Defense. Along the way, he has flown MC-130Js, stood up overseas squadrons, embedded with SOCOM on urgent missions, worked with Silicon Valley venture firms, and guided startups seeking a foothold in the defense market. His career blends real-world operations with lessons from acquisition, venture capital, and policy—a perspective that few others in the defense ecosystem possess.
This blog post unpacks his journey, insights, and lessons for those navigating the complexities of government contracting today.
A Career Built on Serendipity and Service
Underwood’s career wasn’t the result of a meticulously planned roadmap. In fact, it started in a grocery store, where a chance encounter with a wing commander changed the course of his life. Encouraged by mentorship and inspired by the possibility of service, he applied to the U.S. Air Force Academy, launching a career that would take him far beyond what he had imagined.
This theme of mentorship is one he returns to often. A single leader’s guidance, he notes, can influence not only an individual career but also the wider defense ecosystem for decades to come. Mentorship, in his view, is not just about professional development—it’s about shaping the future of national security.
From Special Operations to Acquisition
As a pilot in Air Force Special Operations Command, Underwood experienced the mission side of national defense firsthand. Flying MC-130Js, standing up squadrons overseas, and working alongside SOCOM gave him a perspective few acquisition professionals ever acquire.
That operational grounding became a competitive advantage when he transitioned into acquisition and later into venture capital advising. Having been on the receiving end of technology, Underwood understood which innovations truly advanced the mission and which merely added complexity.
This dual lens—operator and acquisitions leader—gave him clarity on a question many in defense overlook: does the technology solve a real mission-critical problem?
The Complexities of Defense Acquisition
One recurring theme in Underwood’s career is the inherent tension within defense acquisition: speed versus bureaucracy.
The Department of Defense urgently needs to move faster, especially as global adversaries adopt emerging technologies at unprecedented rates. Yet the acquisition process is designed for accountability, oversight, and taxpayer protection—factors that often slow down innovation.
Underwood sees this duality as both frustrating and necessary. Federal regulations like the FAR, cybersecurity certifications like CMMC, and systems like FedRAMP create bottlenecks—but they also ensure responsible stewardship. The challenge, he argues, is in striking the right balance.
Product–Mission Fit: The Key to Winning
For startups trying to break into defense, Underwood emphasizes that the best product on paper doesn’t always win. Success depends on what he calls product–mission fit.
Technology must align with real-world mission needs. A flashy tool with no operational utility will fall flat, while even a modest solution that directly supports a warfighter’s objectives can gain traction quickly.
For companies, this requires more than technical brilliance—it requires listening, understanding the operational environment, and translating innovation into mission outcomes.
The SOCOM Model: Speed Meets Urgency
Special Operations Command (SOCOM) stands out as a model of what’s possible in defense acquisition. SOCOM’s smaller scale, urgency, and agile culture allow it to adopt and deploy technology far faster than traditional service branches.
From embedding acquisition officers directly with operators to running initiatives like the “ghost program” (where junior officers immerse in SOCOM to learn acquisition), SOCOM demonstrates how bureaucracy can be trimmed without sacrificing accountability.
Underwood believes the broader DoD could learn much from this model.
Bridging the Gap Between Startups and the Pentagon
One of Underwood’s unique perspectives comes from his time working alongside Silicon Valley venture capital. There, he saw how difficult it is for even the most promising startups to navigate the defense market.
The problem, he explains, is rarely the technology itself—it’s the communication gap. Startups often fail to frame their solutions in ways that resonate with government buyers, while the Pentagon sometimes struggles to fully grasp the potential of emerging commercial innovations.
Today, much of his work centers on closing that gap: helping startups translate their value into mission terms and helping DoD leaders recognize the potential in cutting-edge commercial technology.
The Next Wave: AI, Cyber, and Space
Looking ahead, Underwood points to three areas where defense investment is accelerating: artificial intelligence, cybersecurity, and space. These domains represent both opportunity and risk, and they are where the government is directing increasing resources.
By contrast, sectors tied to legacy solutions or compliance-heavy systems are losing traction. For founders and business leaders, the lesson is clear: follow the money, but more importantly, follow the mission priorities.
Reform on the Horizon
Defense acquisition is entering a period of change. Legislation like the FORGE Act and SPEED Act, along with expanded use of Other Transaction Authorities (OTAs), signals a shift toward cutting red tape and bringing in non-traditional players.
Underwood sees this as the calm before a storm of reform. For startups, this could mean new contract vehicles, faster pathways, and expanded opportunities. For the DoD, it represents a chance to rethink decades of acquisition culture.
Lessons for Founders and Leaders
Underwood’s experiences yield several key lessons:
Mentorship matters. One leader’s guidance can change careers and ripple across the defense ecosystem.
Operational grounding is critical. Acquisition leaders with mission experience make better decisions.
Product–mission fit drives success. Winning isn’t about the “best” product—it’s about solving the mission problem.
SOCOM offers a blueprint. Speed and agility in acquisition are possible—and replicable.
Bridging cultures is essential. Startups must learn to speak “Pentagon,” and the DoD must learn to understand startups.
The next frontier is clear. AI, cyber, and space are where the biggest opportunities lie.
Final Reflections: Charting the Future of Defense Innovation
Forrest Underwood’s story is more than a personal journey—it’s a reflection of the challenges and opportunities shaping the future of government contracting. From the cockpit of a special operations aircraft to advising senior defense leaders at the Pentagon, he has witnessed firsthand how culture, technology, and leadership collide in the defense ecosystem.
The message he carries forward is clear: the defense sector is at a turning point. Startups, innovators, and acquisition leaders face an unprecedented opportunity to reshape how technology supports the mission. But success will require more than ideas—it will demand alignment with mission needs, reform-minded thinking, and the relationships that make innovation possible.
In a landscape marked by bureaucracy, urgency, and global competition, Underwood stands as both a guide and a bridge—connecting the speed of Silicon Valley with the scale of the Pentagon. For those looking to enter or expand in the defense market, his insights are not only timely but essential.
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