20 Oct October 20, 2025 – AI Medicare Alex Doonanco and Greatest Hits VC Ann Winblad
Alex Doonaco – Co-founder & CEO of careCycle (YC W25)
I think the technology is going to be commoditized eventually… so in order to build a really generational or defensible business here, we need to find a way to embed very vertical-specific knowledge into it, solve very specific problems, and build a platform around it.
Alex Doonanco
Alex Doonanco is the CEO and Co-founder of careCycle, where he leads the development of AI voice teams that have transformed Medicare agency operations, having over 400,000 conversations with seniors since October 2024. With deep expertise in conversational AI and healthcare technology, Alex previously served as the first U.S. hire and GTM lead at AI Rudder, architecting contact center automation projects across several B2C industries. As an early leader in voice AI application development, he regularly shares insights on the transformative power of well-architected solutions for business interactions with customers. Recognized for pioneering the AI communication layer for medicare distribution, Alex is passionate about democratizing enterprise-grade technology to ensure every senior receives the consistent, high-quality care they deserve. The platform delivers measurable impact, including up to 40 percent lower acquisition costs and 37 percent higher effectuation rates.
Ann Winblad – Co-Founder & Managing Director Hummer Winblad Venture Partners
Our job is not to predict the future, but to purchase it, and I believe that you really got to be very open minded….
Ann Winblad
Ann Winblad is the Co-Founder and Managing Director of Hummer Winblad Venture Partners, the first venture capital firm to focus exclusively on software. A pioneering entrepreneur turned investor, she began her career as a systems programmer at the Federal Reserve Bank of Minneapolis before co-founding Open Systems, Inc., an accounting software company she later grew and sold successfully. In 1989 she co-launched Hummer Winblad, where she has since helped build and scale more than 160 enterprise software companies across analytics, cloud computing, cybersecurity, and infrastructure. With a background in mathematics and business administration from St. Catherine University and a master’s degree from the University of St. Thomas, Winblad is widely regarded as one of the most influential figures in early enterprise software investment. Beyond venture capital, she serves on educational and nonprofit boards and continues to mentor founders at the intersection of innovation, strategy, and technology.