Rob May

Overview

Rob May is a seasoned entrepreneur and angel investor with over two decades of experience in the technology industry. He is the founder and CEO of BrandGuard, an artificial intelligence brand management company. Prior to BrandGuard, Rob co-founded Talla, a company specializing in artificial intelligence and automation for workplace productivity enhancement. As CEO of Talla, he successfully guided the company through multiple rounds of funding, earning recognition for its innovative AI solutions. Before Talla, Rob founded Backupify, a pioneering cloud-to-cloud backup platform for SaaS applications, which he led to become a market leader in cloud data protection before its acquisition by Datto. Rob's career also includes roles as a Venture Partner at Pillar VC, a General Partner at PJC, and managing an AI-focused angel investment fund, Half Court Ventures. Beyond his executive roles, Rob remains active in the Boston startup community as an angel investor, mentor to aspiring entrepreneurs, and frequent speaker and writer on innovation and technology. Passionate about driving growth and success, Rob continues to make significant contributions to the companies he supports. Rob's investment focus includes early-stage technology startups, particularly in sectors such as artificial intelligence, analytics, customer relationship management (CRM), software as a service (SaaS), sales automation, machine learning, marketplaces, online portals, retail, and sales. He typically invests between $10,000 and $500,000 in seed, pre-seed, and Series A funding rounds, primarily within the United States. His portfolio reflects a strong thematic focus on AI and related technologies, demonstrating his commitment to fostering innovation in these rapidly evolving fields. Through his ventures and investments, Rob has demonstrated a keen ability to identify and nurture high-potential startups, guiding them from inception to successful exits. His leadership at Talla and Backupify showcases his expertise in scaling technology companies and his dedication to advancing the adoption of artificial intelligence in business operations. Rob's active involvement in the startup ecosystem underscores his passion for innovation and his commitment to supporting the next generation of entrepreneurs.