Caleb Hailey is a serial entrepreneur and founder based in Portland, Oregon with 13 years of formal experience and nearly two decades of hands-on work in distributed systems and cloud-native infrastructure. He co-founded and led Sensu from early productization through a successful acquisition by Sumo Logic, later serving as Senior Director of Product to integrate that technology at scale. Caleb combines product leadership, developer advocacy, and open-source stewardship—launching a cloud-native observability product used by thousands and maintaining open core projects. He has a proven track record of turning consulting practices into product businesses, raising venture capital, and retaining teams through transitions. A longtime remote-work advocate and two-time tech conference founder, he quietly specializes in “everything as code” automation and Kubernetes-centered initiatives. Now leading Herd Works in stealth, he focuses on building developer-first cloud infrastructure solutions with product-market rigor.
13 years of coding experience
7 years of employment as a software developer
Web/Multimedia Management and Webmaster, Web/Multimedia Management and Webmaster at Mt. Hood Community College
Sensu Go handler for implementing "self healing" workflows
Contributions:16 releases, 9 PRs, 21 pushes in 3 years 3 months
golangsensu-goself-healinggohealing
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