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February 19 2026

KippsDeSanto & Co. advises Ask Sage, Inc. on its sale to BigBear.ai

KippsDeSanto & Co. is pleased to announce the sale of its client, Ask Sage, Inc. (“Ask Sage” or the “Company”), to BigBear.ai (NYSE: BBAI) for $250 million. This transaction underscores the surging demand for secure, mission-critical AI infrastructure and highlights Ask Sage’s position as a premier vertical SaaS provider of generative AI capabilities for the defense and national security sectors.

Founded by Nicolas Chaillan, former Air Force and Space Force Chief Software Officer, Ask Sage was purpose-built for government and other highly regulated sectors to overcome the challenges of security, compliance, and vendor lock-in. At the time of closing, Ask Sage supported more than 100,000 users across 16,000 government teams and hundreds of commercial organizations.

KippsDeSanto & Co. believes this transaction highlights several key themes in the AI and Defense Tech M&A markets:

- Significant market demand for vertical-focused SaaS providers with solutions that are deeply embedded with users and create profound operational impact;

- Appetite for scalable AI infrastructure that provides access to a large user footprint and facilitates cross-sell potential of additional capabilities; and

- Prioritization of assets with a competitive moat in highly regulated industries, such as differentiated security authorization in the AI and Defense Tech markets

About KippsDeSanto & Co.

KippsDeSanto & Co. is an investment banking firm focused on serving growth-oriented Aerospace & Defense, Government Technology Solutions, and Enterprise Technology companies. We are focused on delivering exceptional M&A and financing transaction results to our clients via leveraging our scale, creativity, and industry experience. We help market leaders realize their full strategic value. Having advised on more than 250 industry transactions, KippsDeSanto is recognized for its analytical rigor, market insight, and broad industry relationships. There’s no substitute for experience. For more information, visit www.kippsdesanto.com.

Investment Banking products and services are offered through KippsDeSanto & Co., a non-bank subsidiary of Capital One, N.A., a wholly-owned subsidiary of Capital One Financial Corporation, and a member of FINRA and SIPC. Products and services are Not FDIC insured, Not Bank Guaranteed, May Lose Value, Not a Deposit, and Not Insured by Any Federal Government Agency.

KippsDeSanto & Co. is pleased to announce the sale of its client, Ask Sage, Inc. (“Ask Sage” or the “Company”), to BigBear.ai (NYSE: BBAI) for $250 million. This transaction underscores the surging demand for secure, mission-critical AI infrastructure and highlights Ask Sage’s position as a premier vertical SaaS provider of generative AI capabilities for the defense and national security sectors.

Founded by Nicolas Chaillan, former Air Force and Space Force Chief Software Officer, Ask Sage was purpose-built for government and other highly regulated sectors to overcome the challenges of security, compliance, and vendor lock-in. At the time of closing, Ask Sage supported more than 100,000 users across 16,000 government teams and hundreds of commercial organizations.

KippsDeSanto & Co. believes this transaction highlights several key themes in the AI and Defense Tech M&A markets:

- Significant market demand for vertical-focused SaaS providers with solutions that are deeply embedded with users and create profound operational impact;

- Appetite for scalable AI infrastructure that provides access to a large user footprint and facilitates cross-sell potential of additional capabilities; and

- Prioritization of assets with a competitive moat in highly regulated industries, such as differentiated security authorization in the AI and Defense Tech markets

About KippsDeSanto & Co.

KippsDeSanto & Co. is an investment banking firm focused on serving growth-oriented Aerospace & Defense, Government Technology Solutions, and Enterprise Technology companies. We are focused on delivering exceptional M&A and financing transaction results to our clients via leveraging our scale, creativity, and industry experience. We help market leaders realize their full strategic value. Having advised on more than 250 industry transactions, KippsDeSanto is recognized for its analytical rigor, market insight, and broad industry relationships. There’s no substitute for experience. For more information, visit www.kippsdesanto.com.

Investment Banking products and services are offered through KippsDeSanto & Co., a non-bank subsidiary of Capital One, N.A., a wholly-owned subsidiary of Capital One Financial Corporation, and a member of FINRA and SIPC. Products and services are Not FDIC insured, Not Bank Guaranteed, May Lose Value, Not a Deposit, and Not Insured by Any Federal Government Agency.