Manny Medina

Manny Medina is a serial entrepreneur with a proven track record of building and scaling successful software companies. He co-founded Outreach, a sales engagement platform that achieved a $4.4 billion valuation, and is now pioneering the AI agent monetization space with his new venture, Paid.ai. paid+2

Medina is an advocate for a new approach to AI pricing, moving away from traditional SaaS seat-based models towards outcome-based and agent-based billing. He believes in specialized AI applications that solve narrow, high-friction problems for specific customer segments, rather than broad platforms, and emphasizes the importance of understanding unit economics in the AI era. paid+2

His career demonstrates a blend of technical expertise and leadership, having held roles at Amazon AWS (employee #3 on the AWS team) and leading Microsoft's mobile division to $50 million in annual revenue, before embarking on his entrepreneurial journey. He holds advanced degrees in Computer Science and Business Administration. clay+3

Medina's leadership style is characterized by authenticity, transparency, and a focus on fostering a culture where employees can bring their 'whole selves to work'. He advocates for open discussions on meaningful topics, believing it builds trust, rapport, and a strong community within a company. mayfield+1