Building the AI-Native Enterprise: Leadership, Software, and Compounding with Mahesh Rajasekharan - EP.286

Mahesh Rajasekharan has spent over twenty-five years in supply chain and leads Cleo, a category leader in AI-driven supply chain orchestration serving more than five thousand customers globally. In this episode of Think Like an Owner, Alex Bridgeman, Rob Southern, and Mahesh explore how AI is fundamentally reshaping enterprise software and what it means to build an AI-native company. Mahesh shares how Cleo combines powerful intelligence with accumulated data, context, and domain expertise to close the gap between planning and execution in complex supply chain environments.

They discuss:

- Why AI amplifies existing strengths rather than creating value from weak foundations

- How software production has shifted from humans writing code to humans defining problems while agents participate in building

- The economic discipline required when allocating capital across frontier models, open-source alternatives, and purpose-built solutions

- Why supply chain orchestration represents a structural opportunity to coordinate action across multi-enterprise ecosystems

- How clarity of purpose, exceptional talent, and leading transformation from the front become even more critical in the AI era

This episode offers practical insight for software leaders and business owners navigating technology transitions while maintaining long-term compounding growth.

Topics:

(00:00:00) - Intro

(00:00:57) - Mahesh's background and Cleo's mission

(00:03:20) - What AI-first actually means