This consultant advised Big Law at McKinsey. Now Sequoia is backing his AI startup for in-house lawyers.

The legal industry is navigating a complex relationship with artificial intelligence, as tools designed to enhance lawyer efficiency could inadvertently reduce billable hours. This reality hit Nick Fleisher hard during his tenure at McKinsey, where he assisted prestigious law firms in integrating technology—often facing resistance from the very lawyers expected to utilize these innovations. Fleisher's experiences at McKinsey propelled him to establish his own company, Sandstone, in August. Targeting in-house legal teams rather than traditional law firms, Sandstone has secured $10 million in seed funding led by Sequoia Capital, with additional backing from investors such as Kearny Jackson and SV Angel, as well as corporate general counsels from companies like eBay. Based in Brooklyn, Sandstone utilizes AI to help in-house lawyers streamline the drafting and review of contracts by analyzing how similar agreements were handled in the past. Fleisher, a Wharton School graduate, was part of a team at McKinsey that collaborated closely with QuantumBlack, the firm's AI division, on projects like creating an 'AI arbitrator' for construction disputes. In his final months at McKinsey, Fleisher conducted numerous workshops for general counsels who sought to build their own technology strategies without committing to a full McKinsey engagement. He found that many teams were still grappling with fundamental issues, such as the effective use of contract lifecycle management software and tracking external legal expenditures. However, Fleisher noted a significant shift in attitude among general counsels, many of whom were receiving directives from CEOs or boards to adopt AI solutions despite uncertainties about the financial implications. During his off-hours at McKinsey, he partnered with former technology lawyer Jarryd Strydom to develop a task tracker for legal teams. Their initial prototype gained traction among a few in-house lawyers, validating the concept. On the final day of their McKinsey journey, Fleisher and Strydom pitched their startup to Sequoia, which promptly led Sandstone's seed funding round. The startup now boasts several dozen paying customers, primarily from midsize firms with legal departments across various sectors, including software, manufacturing, finance, and insurance. While Sandstone's approach is not entirely novel—companies like Harvey and Clio have similarly ventured into the legal tech space—Fleisher believes that a dedicated system for corporate legal teams is lacking. He envisions Sandstone as a comprehensive platform that integrates legal work with other business functions, enabling seamless collaboration across departments. Through its innovative design, Sandstone allows sales personnel to submit draft agreements via Slack, where the AI system assesses the document against previous contracts and internal guidelines, highlighting potential risks and suggesting revisions before it reaches the appropriate lawyer for final approval. Fleisher asserts that this could allow legal professionals to focus more on critical tasks that require human judgment, rather than being bogged down by administrative requests. Sequoia partner Bogomil Balkansky first learned about Fleisher through the firm's talent acquisition team, which recognized his potential. Although Balkansky initially attempted to recruit Fleisher for a different role, he ultimately supported Fleisher's vision for his own legal tech company, leading to Sequoia's significant investment in Sandstone. As interest in legal tech surges—evidenced by nearly doubling funding from $2.2 billion in 2024 to $4 billion in 2025—Fleisher's venture stands to capitalize on a market ripe for transformation. With over a million lawyers in the U.S. and many companies keen to optimize costs, Fleisher believes that the future of legal AI lies not in traditional hourly billing but in enhancing the efficiency of business operations.