Win Win Aviation, Inc.

Win Win Aviation, Inc., doing business as Win Aviation, is a self-certified small disadvantaged business based in DeKalb, Illinois, that provides military freefall and static line parachuting support services, fixed-wing airlift operations, and specialized aircraft rental to the Department of Defense as a prime contractor on multiple indefinite delivery vehicles. The company operates exclusively as a prime (100% of awards), competing across both set-aside and full-and-open vehicles, with set-aside designations appearing on roughly 40% of recent delivery orders.

Win Aviation's core capability is delivering specialized aviation training and operational support across four primary dimensions: military freefall and static line parachuting (HALO/HAHO operations, ground instruction, and administrative support); fixed-wing airlift services using Sherpa and Skyvan aircraft for rescue squadrons and special operations forces; blade hour aviation services for training and proficiency missions; and aircraft rental with specialized crews for high-risk training exercises. Representative work includes a $1.13 billion delivery order from Naval Special Warfare Command for full-spectrum military freefall and static line support through May 2028, a $3.92 million Navy order for freefall and static line services in Marana, Arizona through October 2026, a $5.43 million single-award contract from Air Force Defense Finance and Accounting Service for fixed-wing airlift at Davis-Monthan through August 2030, and a $4.0 million multiple-award BPA from Air Force Space Command for 920th Rescue Squadron training through January 2029.

Customer concentration sits decisively with U.S. Special Operations Command and Air Force Air Combat Command. SOCOM accounts for 41 awards carrying $1.32 billion in combined potential value—97% of the vendor's total dollar footprint—anchored by the $1.3 billion Military Freefall and Static Line Support Services IDIQ awarded August 25, 2021, through August 24, 2029. Air Combat Command places the most orders (109 awards, 37% of volume), but at lower per-order magnitude ($17.3 million combined), reflecting routine delivery orders for Skyvan and Sherpa airlift to the 48th, 68th, 304th, and 306th Rescue Squadrons. Naval Expeditionary Combat Command (65 awards, $9.7 million) and Army Test and Evaluation Command (18 awards, $1.2 million) round out the active set. The revenue concentration is severe: 41 SOCOM task orders represent 97% of potential value, while 109 ACC awards represent 1.3% despite being nearly three times as numerous.

Win Aviation holds three primary IDVs. The $1.3 billion SOCOM IDIQ for military freefall and static line support (multiple award, no set-aside, through August 2029) is the dominant vehicle, with 73 delivery orders issued and funding flowing from Naval Special Warfare Command, Air Force Special Operations Command, Air Mobility Command, and other SOCOM-aligned customers. The $5.43 million single-award ACC contract for fixed-wing airlift at Davis-Monthan (total small business set-aside, through August 2030) has generated 79 delivery orders under vehicle FA487720D0006, nearly all under $300 thousand. The $247.45 thousand Army Test and Evaluation Command blade hour aviation IDC (total small business set-aside, through April 2026) supports Advanced Base Non-Standard Training and Doctrine requirements. A fourth vehicle, the $4.0 million Air Force Space Command BPA for 920th Rescue Squadron training (multiple award, no set-aside, through January 2029), was awarded December 23, 2024, and represents recent vehicle expansion.

Activity has been steady, ranging from 31 to 46 awards annually over the past five years, with 13 awards recorded in 2026 through May 14. Twelve awards with ultimate completion dates in the next twenty-four months carry combined potential value of $8.3 million—modest recompete exposure relative to the vendor's overall footprint, reflecting the continuing nature of military training and operational support requirements. The SOCOM IDIQ, which expires August 24, 2029, does not face recompete until then, but the company will likely pursue recompete or compete for successor vehicles as renewal nears.

Win Aviation's contract portfolio centers on NAICS 481219 (Other Nonscheduled Air Transportation, 68% of awards) and PSC codes for air charter transportation and aircraft rental. The vendor has no identified subcontract footprint—all 292 awards reflect direct prime performance. The company's business model is transactional and responsive: delivery orders typically range from under $10 thousand to $4.9 million, with firm fixed-price structures and completion dates of days to months, reflecting day-to-day operational and training support rather than large sustained programs. Win Aviation's headquarters and administrative oversight sit in DeKalb, Illinois, but performance is geographically dispersed across military installations including Davis-Monthan Air Force Base (Arizona), Fort Liberty (North Carolina), Hurlburt Field (Florida), Pope Field (North Carolina), Naval Air Station North Island (California), and various drop zones in Arizona, California, and Florida, reflecting its role as a critical logistics and training enabler for special operations and rescue operations across the continental United States and select overseas locations.