Summary
Matt Flaherty is a seasoned technology leader and founder with over a decade of engineering leadership across startups and established companies in the San Francisco Bay Area. He currently guides engineering at Maven AGI and leads Outrigger Solutions as founder/owner, blending hands-on delivery with strategic product and organizational leadership. In past roles, he steered growth engineering at One Medical through IPO and acquisition, built conversational UI teams at Hipmunk, TripIt, and Concur, and founded When Labs to craft union-compliant scheduling experiences. His early career spanned security-centric roles at IBM and Eclipse, giving him a durable focus on secure, reliable systems, while his tech scope covers Ruby on Rails, Python, React, Node.js, AWS, and data platforms. An MIT Sloan and MIT Engineering Management alumnus, he is adept at aligning product, security, and engineering to ship scalable software for a diverse set of industries. Based in San Francisco, California, he brings entrepreneurial grit, cross-stack fluency, and a calm, results-driven leadership style.
11 years of coding experience
17 years of employment as a software developer
SM, Engineering Management, SM, Engineering Management at Massachusetts Institute of Technology
SM, Engineering Management, SM, Engineering Management at Massachusetts Institute of Technology - Sloan School of Management
BS, Computer Science, BS, Computer Science at Syracuse University
Saint John's High School