Winners' Circle

Robert Klamser on Using AI to Make Chapter 11 Bankruptcy Easier to Understand

40 min · 25. maj 2026
episode Robert Klamser on Using AI to Make Chapter 11 Bankruptcy Easier to Understand cover

Description

Robert Klamser is helping make one of the most complex corners of the legal system easier to navigate. As the leader of Stretto’s AI focused innovation efforts, Robert works on technology that supports professionals, creditors, vendors, employees, courts, and other stakeholders involved in bankruptcy cases. Stretto recently won an AI Excellence Award for Conductor, its AI powered platform built to make Chapter 11 information more accessible, understandable, and useful. In this episode, Russ and Robert explore why bankruptcy is such a document heavy, high stakes, and often confusing process. Robert explains how large Chapter 11 cases can involve thousands of pages of filings, multiple jurisdictions, local rules, federal bankruptcy code, and millions of affected stakeholders who may have never encountered bankruptcy before. They dive into Stretto Conductor and how it helps users ask plain language questions about complex bankruptcy documents. Robert shares how the platform is designed to understand filings in the context of the specific case, the related docket history, the bankruptcy code, and the local rules that may shape the answer. The conversation also covers why general purpose AI is not enough for this kind of work. Robert explains the importance of domain specific AI, grounded answers, citations, legal precision, multilingual access, and making sure the platform provides information without crossing into legal advice. Along the way, Robert discusses creditor communications, call center operations, hallucination concerns, attorney trust, AI adoption in the legal industry, and why the future of legal technology will likely depend on purpose built systems that do one thing extremely well. Topics Covered: [00:01] Welcome and intro, Robert Klamser and Stretto’s AI Excellence Award win [00:17] Stretto’s role in bankruptcy support services and technology [02:11] The communication challenges inside large Chapter 11 cases [03:00] How Conductor helps vendors, creditors, and lawyers understand filings [04:34] What is broken about how information flows in bankruptcy cases [06:31] Why basic case information can be hard for stakeholders to access [07:00] How bankruptcy case websites changed access to documents [09:18] Why documents still need context from the bankruptcy code and local rules [10:54] What Stretto Conductor does differently [11:12] Teaching AI the rules, nuance, and structure of bankruptcy [13:31] Why legal AI must be grounded, intelligent, and precise [15:37] Why purpose built AI matters in bankruptcy law [17:02] Why one document rarely tells the full story in a Chapter 11 case [19:20] Naive retrieval, missing context, and reasoning errors in general AI tools [21:01] Building trust with skeptical legal professionals [21:21] Why every answer must be cited and grounded in the right source [22:38] How users are learning to trust Conductor [23:00] Why Conductor answers questions instead of drafting legal documents [24:21] How large bankruptcies create massive temporary operating structures [24:55] Supporting bankrupt entities while the business keeps operating [27:08] Making newly filed documents understandable within minutes [28:00] Multilingual access for stakeholders in global bankruptcy cases [28:54] How Conductor can reduce pressure on large call centers [31:45] Why lawyers have traditionally been slow to adopt new technology [32:27] How courts, caution, and hallucination concerns affect AI adoption [35:53] Where legal AI may be heading over the next five years [37:00] The need for clearer standards around AI use in legal work [38:25] Why clients may soon expect attorneys to use AI efficiently [39:58] Final thoughts on making bankruptcy easier to understand

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episode Katy Irving and Rory Mitchell on AI Avatars in Healthcare Research artwork

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