As a serial entrepreneur turned executive coach, Dileepan works with founders, CEOs, and senior leaders navigating high-stakes growth, transition, and organizational complexity. Over a 20-year career as a builder and operator, he learned that your own strengths and weaknesses are mirrored in the organization you build — and how you relate to your business is often how you relate to other parts of your life. This critical insight, borne out of deep work with exceptional guides, led him down the path of coaching top-tier founders and leaders in their own business and personal transformation journeys.

Dileepan has built, scaled, and sold three venture-backed startups and served as a senior commerce executive at Twitter and eBay. Earlier in his career, he advised leaders at global Fortune 50 companies including PepsiCo and Unilever, as well as public and non-profit institutions including the United Nations, US Department of State, and the Gates Foundation. He brings this breadth of operating and advisory experience directly into his coaching practice.

Dileepan's approach blends rigorous executive coaching with depth psychology and spiritual traditions. He is trained through the Co-Active Training Institute (CTI), Conscious Leadership Group, and Neuro-Linguistic Programming (NLP), and draws on a longstanding meditation and mindfulness practice rooted in Buddhism. He holds a BA from the University of California, Berkeley and an MBA from Harvard Business School.

Born in London, raised in the Middle East, and having lived and worked in over 40 countries across five continents, Dileepan brings a global perspective and deep cross-cultural fluency to his work with leaders. He currently resides in Los Angeles.