Ross Kukulinski

Ross Kukulinski is Vice President of Product at Tailscale, where he leads product strategy and execution across the company's secure connectivity platform. Ross is a technical product leader who builds businesses at the intersection of open source, cloud infrastructure, and developer experience. He has spent nearly two decades working on cloud-native technologies, helping organizations move from early adoption to reliable, large-scale production use. His work has focused on turning complex distributed systems into products that are easier to adopt, operate, and trust—without hiding the underlying engineering or limiting flexibility. Before joining Tailscale, Ross was VP of Product Management at Kong, where he led the transformation from packaged on-prem software to a cloud-first platform. Prior to Kong, he spent four years at VMware following the acquisition of Heptio, where he was an initial employee. At Heptio and VMware, he led product for Kubernetes platforms including Tanzu Kubernetes Grid, working closely with engineering teams and customers to shape how modern infrastructure is packaged, delivered, and operated. Ross is passionate about building products that balance strong technical foundations with clear customer value, mentoring future product leaders, and earning developer trust through great experiences.