In this podcast episode, Jackie shares her personal journey from working as a lawyer to founding Clearbrief, an AI-powered litigation analysis tool that integrates with Microsoft Word to assist with research, citations, and document management. Jackie and Charlie discuss the challenges women founders face in getting venture capital attention and support, even when their offerings are high quality. Jackie spoke about the importance of women legal tech startup leaders speaking confidently about their product and its market prospects (especially when, as was the case with Jackie’s own early product development efforts, the assessment of product prospects is based on feedback arising out of literally hundreds of customer interviews). Charlie and Jackie also talk about the difficulties of marketing a product to senior law firm decision-makers (who, after all, control budgets) based not only on the product’s firm-wide and enterprise-wide benefits but also on the product’s prospects for improving the quality of life for junior lawyers and paralegals. Charlie and Jackie cover the implications of AI on the legal profession, including AI’s potential impact on billing practices as technology continues to drive efficiency.