Nicolas M. Chaillan
Serial Entrepreneur · Former USAF/USSF Chief Software Officer · AI Investor · Author
Key Achievements
- Sold Ask Sage for $250M (2025) — First FedRAMP High authorized GenAI platform for government
- First USAF & USSF Chief Software Officer (2018–2021) — Brought DevSecOps DoD-wide
- Founded 12 companies, sold 180+ products to Fortune 500 — started first company at age 15
- Big Bear.ai CTO (Dec 2025 – Feb 2026) — Ask Sage acquired by Big Bear.ai
- DHS Special Advisor — Designed Cyber.gov architecture for federal cybersecurity
- PHP Pioneer — Recognized contributor to one of the world's most-used programming languages
- Fox News, Epoch Times, major media — 15+ national TV/media appearances on defense & AI
Summary
Nicolas M. Chaillan is a serial entrepreneur, cybersecurity expert, and former senior U.S. government technology leader. He served as the first Air Force and Space Force Chief Software Officer under Dr. William Roper, bringing DevSecOps, continuous Authority to Operate (c-ATO), and modern software practices across the entire Department of Defense.
In 2022, he founded Ask Sage, Inc., the first generative AI platform to achieve FedRAMP High Authorization for government teams. Ask Sage was acquired by Big Bear.ai in 2025 for $250M, and Nicolas served briefly as Big Bear.ai's CTO before departing in February 2026.
Previously, he served as Special Advisor for Cloud Security and DevSecOps at the Department of Defense and Special Advisor for Cybersecurity and Chief Architect for Cyber.gov at the Department of Homeland Security.
Nicolas founded 12 companies starting at age 15, created and sold over 180 innovative software products to Fortune 500 companies, and is recognized as a pioneer of PHP. He has over 25 years of experience in cybersecurity, software development, and government modernization.
He is currently focused on AI investing, authoring "Replacement" — a book on AI's impact on the workforce — and hosting "In the Nic of Time" on LinkedIn and YouTube.
Career Chronology
WorldAKT — Founder and CEO, Marseille, France
GamesAKT — Founder and CEO, Marseille, France
AKT — CEO and CISO, Lyon, France
SOFTAKT — Founder and CEO, Lyon, France
AFTER-MOUSE.COM — Founder and CIO, Washington, DC
anyGuest.com — Founder and CIO, Washington, DC
Holding AKT — Chairman of the Board, New York, NY
Wait List Ordering, LLC — Founder and CEO, Washington, DC
Nesting Partners — Founder and CTO, Washington, DC
Cyber Revolution, Inc. — CISO, Washington, DC
Department of Homeland Security — Chief Architect and Special Advisor for Cybersecurity (IPA), Washington, DC
Prevent Breach — CTO, Washington, DC
Qualys, Inc. (QLYS) — Federal CTO, Washington, DC
Department of Defense, OSD — Special Advisor for Cloud Security and DevSecOps (IPA), Washington, DC
Assistant Secretary of the Air Force (A&S) — Chief Software Officer, Washington, DC
Board member and On Air Host of "In the Nic of Time"
Ask Sage, Inc. — Founder. Sold for $250M (2025)
Big Bear.ai — Chief Technology Officer (CTO), Resigned
Board Memberships and Associations
- March 2022 — Scryb Inc.
- March 2022 — Crowdbotics
- March 2022 — Traceable AI
- February 2022 — Exovera
- January 2022 — Raft Strategic Advisor
- December 2021 — Tetrate
- December 2021 — Security Compass Strategic Advisory
- October 2021 — VivSoft Strategic Advisor
- December 2017 — EC Council
- June 2018 – June 2019 — Forbes Technology Council
- January 2014 – January 2018 — Holding AKT
Professional Certifications
- Apr 2016 — CISSP – (ISC)² Certified Information Systems Security Professional, Certificate 550109
- Jul 2017 — CEH – EC-Council, Certified Ethical Hacker
- Sep 2015 — CompTIA Security+ Certification
Languages
English and French (native)