From Services to Software: How Dual-Use AI Companies Actually Scale Inside Government | The Pair Program Ep94

From Services to Software: How Dual-Use AI Companies Actually Scale Inside Government | The Pair Program Ep94

In this episode of The Pair Program, we’re joined by Darren Kimura, Chairman and Chief Executive Officer of AI Squared, and Abir Ray, CEO of Expression, for a deep dive into what it really takes to scale AI in complex, high-stakes environments. From the “last mile” problem in AI adoption to the realities of deploying technology in government systems, this conversation explores where innovation meets execution, and what breaks along the way.

Inside the episode:

• Why embedding AI into real workflows is harder than building the models
• The “last mile” problem and what it takes to operationalize AI
• How cognitive overload impacts decision-making in AI-driven environments
• The shift from services to scalable software platforms
• Why human-in-the-loop systems are still critical
• What breaks when moving from pilot to production, and how to fix it

About Darren Kimura: Darren is a technology executive, entrepreneur, and venture investor with 30+ years of experience across AI, enterprise software, cybersecurity, and energy. He currently leads AI Squared, focused on secure enterprise and federal AI deployment.

About Abir Ray: Abir is the CEO of Expression, a defense technology firm specializing in AI/ML systems, cloud-native platforms, and cybersecurity. He also teaches at Cornell and is an expert in spectrum operations and trustworthy AI.

This episode is supported by Defense Unicorns

Defense Unicorns builds platform technologies that help deliver mission-critical capabilities faster and more reliably. Their open architecture approach enables secure, scalable systems without vendor lock, creating flexibility across the software ecosystem. Backed by a team of engineers, innovators, and veterans, they bring deep experience across defense and federal tech.

Get in touch at hello@defenseunicorns.com

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