Karthikeyan Janakiraman

About Karthikeyan Janakiraman

As a technology executive with 20+ years of experience, I specialize in building world-class platforms, modernizing legacy systems, and driving enterprise transformation through AI, data, and cloud-native architectures.I’ve led technology at scale from startup velocity to enterprise complexity and delivered results that blend deep technical execution with strategic business impact. At Chewy, I helped grow the company from $2B to $11B+ by re-architecting ecommerce, pharmacy, and healthcare platforms, building AI-driven systems that replaced vendor solutions, and leading high-performance teams from 6 to 280+ engineers.Key outcomes:Built a proprietary AI recommendation engine that drove $100M+ in attributable revenue in its first year replacing a commercial vendor stack.Launched an in-house pharmacy and drug manufacturing platform transforming Chewy into a vertically integrated healthcare provider.Scaled cloud-native platforms across ecommerce and healthcare domains improving observability, resilience, and velocity.I lead with a product mindset and operator discipline aligning technology strategy with business growth, building future-ready architecture, and developing resilient, autonomous leaders. I focus on long-term technical investments, clear decision frameworks, and creating leverage through systems that scale.I bring the depth of a platform architect, the urgency of an operator, and the vision of a transformational leader. My goal: to build technology that is invisible when it works but undeniable in the value it creates.

Experience

1. Chief Technology Officer

   Realtor.com

   Sep 2025 — Present · Austin, TX, US

Education

• Shiv Nadar University Chennai - MBA

  MCA, Computers

  2002 — 2005

• University of Madras

  BCom, Commerce

  1999 — 2002