Kenneth Rivera

Kenneth Rivera is the Vice President of AI Engineering at Growth Acceleration Partners (GAP), where he leads the engineering team behind GAPVelocity AI — the company’s hybrid AI platform for legacy application modernization. With over 24 years of experience as a technology executive and engineering leader managing globally distributed teams, Kenneth is responsible for the architecture, development, and delivery of GAPVelocity’s AI-powered migration tools, including the VB6 AI Migrator, PowerBuilder AI Migrator, and the ByteInsight codebase analysis platform. Before joining GAP, Kenneth spent nearly three years at Microsoft as Director of Customer Success Account Management, where he oversaw a team managing enterprise client relationships across Canada from Microsoft’s Costa Rica hub — a high-exposure role supporting the broader Latin America region. Prior to Microsoft, he served as Chief Technology Officer at UpMeals, a food-tech startup where he led the technology strategy and engineering organization. His earlier career includes five years at Hewlett-Packard as IT Service Delivery Manager for the Procter & Gamble account, and five years at Mobilize.Net (now part of GAP) as General Manager of Customer Success, where he oversaw project delivery, IT operations, HR, and finance. Kenneth’s leadership philosophy centers on what he calls the “Swiss Army Knife” approach — deliberately seeking diverse experiences across engineering, sales, customer success, and business operations to build the broad executive perspective needed to lead at the intersection of technology and business. He has been featured in the Microsoft Alumni Network’s “Beyond the Blue Badge” interview series, where he shared insights on cross-cultural leadership, communication clarity, and building authentic professional relationships. Kenneth holds an MBA and a Bachelor of Engineering in Computer Science, both from Universidad Latina de Costa Rica. He is based in Costa Rica, where he leads GAP’s engineering operations across multiple time zones.