The Kanawai AI Team


Combining Legal, AI, and Cybersecurity to deliver Secure AI Automation

The Founders

Nicolle Cumberland

CEO, Co-Founder

Nicolle is a veteran litigator and former U.S. diplomat. Before co-founding Kanawai AI, she started her career at the LA District Attorney's office, later specializing in Workers' Compensation, insurance and third-party administration litigation for 10 years. At the U.S. Department of State, Nicolle mastered high-stakes negotiations at the US Embassy in Beijing, where her contributions directly shaped foreign policy. Later, as a Google Cloud Sales Leader, she proved her ability to sell complex cybersecurity solutions and AI supporting Foreign Military Sales across the globe. Nicolle is licensed to practice law in the State of California. She has a J.D. from University of Southern California, Gould School of Law.

Nicolle Cumberland

Rob Waters

CTO, Co-Founder

Rob is a visionary and technology execution engine. With 15+ years of IT and AI Architecture experience, Rob has a proven ability to develop and implement cutting-edge solutions for the enterprise. Prior to co-founding Kanawai AI, Rob spent over 6 years at Google engineering secure AI solutions and infrastructure for highly regulated environments across the U.S. Military. He has previously supported global network operations and architecture at Cisco, Forescout, and the U.S. Military. Rob has a Master's in Business Administration from the University of Southern California, a Master's in Cybersecurity from the University of Maryland, Baltimore County.

Rob Waters

Our Team

Olivia Cai

AI Product Engineer

Olivia is an AI product engineer, data strategist, and former e-commerce entrepreneur. Before joining Kanawai AI, she founded and scaled an e-commerce business, driving over 1,380% year-over-year growth in shop visits. She also gained consulting and analytics experience across market research, document processing automation, and AI product strategy at organizations like FTI Consulting, Perplexity, and Outamation. Olivia holds a B.S. in International Business from UC San Diego and is completing her M.S. in Business Analytics with a concentration in Data Science at the USC Marshall School of Business.

Olivia Cai