Sentry, a leading error and performance monitoring tool used by over 90,000 companies including Atlassian, GitHub, and Disney+, has evolved from an open-source project initiated by David Cramer in 2008 to a critical component of the modern software stack. In an episode of the Tractable Podcast, David, the CTO of Sentry, discusses with Kshitij Grover, CTO at Orb, how Sentry grew from a simple error dashboard to a widely adopted tool through strategic decisions, technical challenges, and leadership styles. The conversation highlights Sentry's unique growth strategy influenced by its open-source origins, its adaptability to industry demands, and its approach to AI and brand campaigns, emphasizing how open-source models can drive market share growth. Despite its evolution, Sentry maintains its core functionality while expanding its product offerings to support a diverse range of frameworks and technologies, establishing itself as a well-recognized brand in the tech industry.