Buy Now, Maybe Pay Later - Dealing with Prompt-Tax While Staying at the Frontier

Learn practical strategies for managing the "Prompt-Tax" challenge that occurs when frontier LLMs rapidly evolve and break existing prompts in production systems. Discover how to maintain cutting-edge AI capabilities while minimizing disruption to your development workflow through 18 months of real-world experience building an agentic product for real-estate lawyers. Explore the core challenge of maintaining an evolving prompt library that breaks with each model upgrade, and master bare-bones tactics that actually work for faster model migrations. Understand the "betting on the model" philosophy of shipping the newest frontier model even when rough around the edges, then racing to close gaps before competitors. Gain actionable insights for handling busted prompts, managing cranky domain experts, and dealing with delayed evaluation results. Walk away with a comprehensive playbook to stay at the AI frontier without derailing your roadmap or overwhelming your team.