Ironclad, a pioneer in deploying generative AI in legal tech, has achieved significant success by integrating AI tools into familiar interfaces like Microsoft Word, making it easier for lawyers to adopt their technology. Founded by Raza Habib and Cai Gogwilt, Ironclad offers AI products that automate contract review and negotiation, with over 50% of contracts at top clients, including OpenAI, being processed by AI. Despite initial challenges that nearly led to abandoning their AI agents project, Ironclad succeeded by developing Rivet, an open-source AI agent builder that simplifies debugging and iteration. Gogwilt advises product leaders to move quickly and boldly in adopting AI, emphasizing the importance of fitting AI features into existing workflows and launching early to gather user feedback. The company's experience underscores the necessity of robust tooling for evaluating and debugging AI applications to ensure reliability and alignment with user needs.