Win Win Aviation, Inc.

Win Win Aviation, Inc., doing business as Win Aviation, a self-certified small disadvantaged business headquartered in DeKalb, Illinois, provides military freefall and static line parachuting support, fixed-wing airlift operations using Sherpa and Skyvan aircraft, and specialized aircraft rental to the Department of Defense as a prime contractor across 300 federal awards totaling $1.36 billion in combined potential value.

Win Aviation operates exclusively as a prime contractor with no subcontract footprint. The vendor's capability portfolio centers on three core service lines: military freefall and static line parachuting instruction and support, including HALO/HAHO (High Altitude Low Opening/High Altitude High Opening) training; fixed-wing airlift operations and blade hour aviation services for rescue squadrons and special operations forces; and aircraft rental with crew support for training missions. Representative contracts include a $3.92 million delivery order from the Navy for military freefall and static line support services at Marana, Arizona (January 2025); a $713.2 thousand purchase order from Air Mobility Command for Navy ICEX Arctic Exercise support at Prudhoe Bay, Alaska (February 2026); and a $483.8 thousand purchase order from Air Force Special Operations Command for 22 STS military freefall jump support at Hurlburt Field, Florida (November 2025).

Customer concentration is extreme and driven by one anchor customer. The top five funding agencies by award count account for 84% of recent awards, but the dollar distribution is heavily skewed: U.S. Special Operations Command accounts for 41 awards carrying $1.32 billion combined potential value—97% of the entire portfolio—despite representing only 14% of the award count. Air Combat Command comes second with 112 awards worth $17.5 million. Navy Expeditionary Combat Command holds 65 awards valued at $9.7 million. This split reveals a customer concentration profile where SOCOM dominates dollars through large single delivery orders while Air Combat Command and Navy commands anchor volume through smaller routine airlift and training task orders.

Win Aviation holds five parent vehicles anchoring its prime portfolio. The Military Freefall and Static Line Support Services IDIQ—a $1.3 billion multiple-award vehicle awarded by U.S. Special Operations Command on August 25, 2021, and running through August 24, 2029—serves as the cornerstone, with 77 task orders carrying $28.2 million in combined potential value. Win Aviation also operates a $5.43 million single-award Indefinite Delivery Contract with Air Force Defense Finance and Accounting Service for fixed-wing airlift services at Davis-Monthan Air Force Base (award date August 13, 2025, through August 12, 2030), designated as a total small business set-aside. A $4 million multiple-award Blanket Purchase Agreement with Air Force Space Command supporting the 920th Rescue Squadron's training requirements runs through January 12, 2029. The company holds a $247.5 thousand single-award IDC with Army Test and Evaluation Command for ABNSOTD blade hour aviation services (April 7, 2023, through April 4, 2026). Delivery orders under the Air Combat Command vehicle (FA487720D0006) total 79 task orders worth $3.5 million combined.

Activity has remained relatively steady over the past five years, with 34 awards in 2022, 31 in 2023, 46 in 2024, 40 in 2025, and 21 in 2026 year-to-date. Five awards face ultimate completion inside the next twenty-four months, carrying combined potential value of $6.6 million. Obligated dollars across all awards total $36.9 million, representing only 3% of combined potential value—typical for IDV vehicles where ceiling values are established upfront but invoiced incrementally against task orders.

Win Aviation operates across fifteen distinct federal agencies but concentrates almost entirely within the Department of Defense: Air Combat Command, U.S. Special Operations Command, Naval Expeditionary Combat Command, Air Force Special Operations Command, Army Test and Evaluation Command, Air Mobility Command, Air National Guard, Navy, Marine Corps, and Air Forces Europe and Africa. The vendor competes under small business set-aside posture—specifically total small business and small disadvantaged business designations—on a majority of Air Combat Command awards and select Army and Air National Guard orders, while competing full-and-open on most U.S. Special Operations Command delivery orders. Work is performed across multiple locations including Davis-Monthan Air Force Base (Arizona), Marana (Arizona), Hurlburt Field (Florida), Fort Story (Virginia), Fort Liberty (North Carolina), and Pope Field (North Carolina), with administrative headquarters at DeKalb, Illinois.