Ask Sage, a generative artificial intelligence startup founded in 2023 by Nicolas Chaillan and based in Front Royal, Virginia, has secured a new multi-million dollar partnership with the Department of Defense to further deploy its technology across the US military. The deal follows a previous five-year agreement under which Ask Sage´s platform became integral to the Army´s ´Enterprise Large Language Model Workspace,´ supporting tasks from rewriting personnel descriptions to automating press releases and optimizing operational workflows. The workspace is already deployed for office operations and enhancing ´warfighter readiness´, signaling the Pentagon´s evolving focus on artificial intelligence-driven speed and efficiency in various mission-critical scenarios.
Ask Sage’s generative tools, authorized for both classified and unclassified settings, are built to meet stringent government security standards, including FedRAMP High certification. According to CEO Chaillan, who previously served as chief software officer for the Air Force, this level of official trust is key to scaling artificial intelligence throughout Department of Defense operations. Currently, more than 15,000 teams across 27 federal agencies are using Ask Sage’s platform for tasks such as code generation, rapid response to government RFPs, and complex data analysis. The startup, which operates a remote team of over 20 employees, also completed a series A round in late 2024, further fueling its growth and ability to serve increasingly complex federal contracts.
The latest contract will fund expansion of Ask Sage’s proven technology beyond the Army, making it accessible to Combatant Commands, the Joint Staff, and top Pentagon offices. Rather than creating new products, the effort centers on scaling up established, policy-compliant tools for acquisition, cybersecurity, logistics, and military operations—areas where, according to Chaillan, automated generative artificial intelligence has significantly shortened compliance timelines and acquisition cycles. The ongoing shift toward commercial procurement models, reinforced by an executive order in April 2025, is enabling broader adoption of solutions like Ask Sage across federal agencies, encouraging competition and reducing reliance on custom, in-house government software. Outside its military focus, Ask Sage is also collaborating with cloud and tech giants including Microsoft, AWS, Meta, Nvidia, and Google through various Department of Defense industry initiatives.
