Summary
Gagan Maheshwari is a product-first founder and former PayPal Head of Product with 11+ years of experience turning complex fintech and enterprise mandates into production-ready platforms and measurable revenue. He began as a software engineer and architect, which informs his pragmatic approach to product, risk, and operations—closing the gap between executive ambition and engineering reality. At PayPal he drove $200M+ in net-new revenue, launched embedded payments with Fortune 50 partners, and deployed AI/ML models that added $15M in incremental checkout revenue while acquiring 750K customers. As Founder and CPO of Orlaya he now serves as a fractional and interim product leader, specializing in payments, platform modernization, and AI governance, and has a track record of cutting OPEX and accelerating time-to-first-transaction. He also founded an AI-driven recruiting startup that scaled to eight-figure revenue, reflecting an uncommon blend of operator grit, technical depth, and commercial execution.
11 years of coding experience
16 years of employment as a software developer
Executive Education, Executive Education at Massachusetts Institute of Technology
Executive Education, Executive Education at INSEAD
Bachelor of Engineering (BE/B.Tech), Computer Science, Bachelor of Engineering (BE/B.Tech), Computer Science at Savitribai Phule Pune University