Oh Advisory

Oh Advisory is founded on a simple premise: Most organizations don't fail because of their tech stack. They stall because of broken feedback loops, organizational friction, and cultures that quietly punish candor. Our work begins where standard playbooks end: with a rigorous diagnosis of an organization's true operating system. This premise is the culmination of a 20-year career leading technology and product at every scale—from building investment banking systems to scaling marketplace platforms at Etsy and Shutterstock to architecting subscription products in healthtech. In 2023, I established this practice to formalize this life's work. The central project is the development of proprietary frameworks on systemic risk and organizational design, a body of research currently being authored as a book-length manuscript. This deep, first-principles research is the foundation of the advisory practice. It is applied across several core areas: → Systemic Technology Strategy: Anticipating next year's problems, not just next sprint's tickets, by treating architecture as a function of the entire organization. → Organizational Diagnosis & Design: Building engineering cultures where psychological safety and high performance are mutually reinforcing. → First-Principles Product: Aligning roadmaps with foundational truths, not political drift. → Leadership Development: Transforming senior talent into strategic thinkers who can navigate complexity. The firm engages with a select number of leaders and organizations—typically those facing complex, systemic challenges where standard solutions have failed. The approach is recursive and reflective, grounded in the belief that the best outcomes emerge from asking uncomfortable questions with intellectual rigor and radical candor.