Crosby wants to insure its AI agents—so it can deploy bots that bill for unsupervised work

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</style><style></style></head><body class="a" style="margin:0px auto;padding:0px;word-wrap:normal;word-spacing:normal;background-color:#FFFFFF;"><div role="article" aria-roledescription="email" aria-label="email_name" lang="en" style="font-size:1rem"><div style="display:none;max-height:0px;overflow:hidden;"> Plus, CLO shares 5-part prompting framework  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ </div><table role="none" width="100%" border="0" cellspacing="0" align="center" cellpadding="0" class="gg"><tr><td align="center" valign="top"><table role="none" width="670" border="0" cellspacing="0" cellpadding="0" class="aa" style="width:670px;table-layout:fixed;"><tr><td class="bodyWrapper" align="center" valign="top" style="padding:0px 5px 0px 5px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td align="center" valign="top" style="border-width:0px 0px 0px 0px;border-style: solid; border-color: #030712FF;border-radius:0px 0px 0px 0px;background-color:#FFFFFF;" class="c"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr id="header"><td style="padding:0px 0px 0px 0px;"><div style="padding-top:0px;padding-right:0px;padding-bottom:20px;padding-left:0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td class="f" align="right" valign="top"><p> August 04, 2026 </p></td></tr></table></div></td></tr><tr id="content-blocks"><td class="email-card-body" align="center" valign="top" style="padding-bottom:0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td align="center" valign="top" style="padding-bottom:20px;padding-left:0px;padding-right:0px;padding-top:20px; " class="dd"><table role="none" border="0" cellspacing="0" cellpadding="0" style="margin:0 auto 0 auto;"><tr><td align="center" valign="top" style="width:660px;"><img src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80,width=1920,height=3840/uploads/asset/file/a11935c7-f948-4ef9-aab5-e4f384c8b445/Frame_76_2x.png?t=1775918098" alt="" height="auto" width="660" style="display:block;width:100%;" border="0"/></td></tr></table></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#d6d6d6;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(252, 25, 25);font-size:0.8rem;"><b>TODAY’S </b></span><span style="color:rgb(252, 25, 25);font-size:0.8rem;font-weight:400;"><b>REDLINES</b></span></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(10, 10, 10);font-family:monospace;font-size:14px;font-weight:400;"> </span>• Crosby plans to insure its AI agents </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(10, 10, 10);font-family:monospace;font-size:14px;font-weight:400;"> </span>• OpenAI agent hacks Hugging Face </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(10, 10, 10);font-family:monospace;font-size:14px;font-weight:400;"> </span>• Perplexity is hiring a Legal AI Strategist </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(10, 10, 10);font-family:monospace;font-size:14px;font-weight:400;"> </span>• 9 rules for legal prompting </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="font-family:Arial, "Helvetica Neue", Helvetica, sans-serif;"><i>5-minute read</i></span></p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(252, 25, 25);font-family:Arial, Helvetica, sans-serif;font-size:0.8rem;font-weight:700;"><b>TRACKED CHANGES</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h1 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><b>Crosby wants to insure its AI agents—so it can deploy bots that bill for unsupervised work</b></h1></td></tr><tr><td align="center" valign="top" style="padding-bottom:20px;padding-left:0px;padding-right:0px;padding-top:20px; " class="dd"><table role="none" border="0" cellspacing="0" cellpadding="0" style="margin:0 auto 0 auto;"><tr><td align="center" valign="top" style="width:636px;"><img src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80,width=1920,height=3840/uploads/asset/file/556e9fe0-4023-4f70-af8f-b475a535c0d8/Newsletter_Image__3_.jpg?t=1785805807" alt="" height="auto" width="636" style="display:block;width:100%;border-radius:0px 0px 0px 0px;border-style:solid;border-width:0px 0px 0px 0px;box-sizing:border-box;border-color:#E5E7EB;" border="0"/></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> Crosby, an AI-native law firm that raised $60M in March, <a class="link" href="https://www.linkedin.com/posts/crosbyryan_we-are-starting-on-the-next-chapter-of-ugcPost-7487592613617745921-woO_/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=12612039e588e6cb64cef8e2c602f0e3d45aca7f" target="_blank" rel="noopener noreferrer nofollow"><span>announced on LinkedIn</span></a> that it is taking out professional liability insurance for its AI agents so they can do legal work <i>without</i> humans in the loop. </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><b>The details:</b></p></td></tr><tr><td style="padding-bottom:20px;padding-left:10px;padding-right:10px;padding-top:10px;" class="ee"><div style="margin-left:0px;" class="edm_outlooklist"><ul style="font-weight:400;list-style-type:disc;margin-bottom:12px !important;margin-top:12px !important;padding:0px 0px 0px 0px;"><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> Today, lawyers review every Crosby output. But CEO Ryan Daniels says agents have improved so quickly that this safeguard “won’t be necessary” for some work. </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> A demo shows the intended end state: a user asks a contract question and receives an “insured output” directly from a Crosby agent. </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> Crosby is working with auditors to define evals, plus bar associations, state regulators, and insurers. A carrier hasn’t been named yet. </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> Corgi, an AI insurance startup, <a class="link" href="https://www.artificiallawyer.com/2026/05/05/corgi-launches-ai-liability-insurance/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=5d9722fe3607570a1229f7deab1702448c1e3668" target="_blank" rel="noopener noreferrer nofollow"><span>launched</span></a> liability coverage for AI failures in May. Crosby could become an early test of this emerging market. </p></li></ul></div></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><b>Why it matters: </b>There are two ways to read this. One is that Crosby found the unlock for AI-native firms: remove costly lawyer review while giving clients financial protection when something goes wrong. The other is that the marketing is way ahead of reality. Insurance doesn’t magically turn an agent into a lawyer, and Crosby has not said what its proposed policy would actually cover. Still, AI-native firms are <a class="link" href="https://aifirmindex.com/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=26ca7507dd37e9eac5a8c1fda4131a365fb819d9" target="_blank" rel="noopener noreferrer nofollow"><span>multiplying fast</span></a>, and the rules for autonomous legal work remain unsettled. If Crosby wins over clients, insurers, and regulators, I’d expect rivals to follow. </p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(252, 25, 25);font-size:13px;"><b>FOR REVIEW</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h2 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><span style="font-family:Arial, "Helvetica Neue", Helvetica, sans-serif;"><b>Other stories</b></span></h2></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.nbcnews.com/tech/tech-news/openai-says-ai-models-went-rogue-testing-triggering-unprecedented-brea-rcna588611?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=94f76179afff51a44df281843dab361e6608614a" target="_blank" rel="noopener noreferrer nofollow"><span>OpenAI agent escapes</span></a> security test and hacks Hugging Face—but who’s liable? </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.wsj.com/business/david-fox-lawyer-big-law-ai-304ec652?mod=e2tw&utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=85624815d90c35c8503d657b5a01f49460eb7406" target="_blank" rel="noopener noreferrer nofollow"><span>David Fox launches Irving</span></a>, an AI-native firm challenging the BigLaw model he built. </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://news.bloomberglaw.com/business-and-practice/the-hottest-job-at-big-law-firms-is-becoming-difficult-to-fill?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=0d3ea39946d85079473d804130bce01f3f4c329d" target="_blank" rel="noopener noreferrer nofollow"><span>BigLaw's hottest new job</span></a> is a $440K AI director role nobody can fill. </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.reddit.com/r/biglaw/comments/1v9zj7j/when_is_ai_use_from_a_junior_embarrassing_and/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=efa40bce2e5c3a4f82cedac7f94e55e271f3f26f" target="_blank" rel="noopener noreferrer nofollow"><span>Redditor asks r/biglaw</span></a>: “when is AI use from a junior embarrassing and when is it not.” </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.globallegalpost.com/news/legora-acquires-uk-ai-litigation-intelligence-start-up-wexler-1776300633?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=a58196420ee223346f4cbca11ea869726c7fb0e6" target="_blank" rel="noopener noreferrer nofollow"><span>Legora buys its way</span></a> into litigation with Wexler, acquisition No. 5 of 2026. </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://techcrunch.com/2026/07/14/google-faces-another-ai-training-lawsuit-from-major-publishers/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=e0225b0b408f21086da8887d3cc979ea068fc9cf" target="_blank" rel="noopener noreferrer nofollow"><span>Hachette, Elsevier, and Scott Turow</span></a> drag Google to court over Gemini training. </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.workplaceprivacyreport.com/2026/07/articles/uncategorized/alabama-state-bar-issues-ai-ethics-guidance-for-lawyers-key-questions-and-practical-answers/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=bbda13c4c7ddf4e89c27f770770a06761719e2db" target="_blank" rel="noopener noreferrer nofollow"><span>Alabama's bar tackles</span></a> the AI billing question—can you bill hours for minutes of work? </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://x.com/paulg/status/2078807311263392182?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=6b1b6105b246c415b7fc230ff0764016388e2847" target="_blank" rel="noopener noreferrer nofollow"><span>Paul Graham blames trial lawyers</span></a> for slowing self-driving cars; post goes viral. </p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(252, 25, 25);font-size:13px;"><b>CAREER MOVES</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h2 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><span style="font-family:Arial, "Helvetica Neue", Helvetica, sans-serif;"><b>Legal AI jobs</b></span></h2></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.linkedin.com/jobs/view/4444044166/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=4a0bf7a11ae20178ce876796e6956df8f7f7f7d6" target="_blank" rel="noopener noreferrer nofollow"><span>AI Strategist, Legal</span></a> @ Perplexity<br></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://job-boards.greenhouse.io/anthropic/jobs/5160459008?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=cb16766d2e94f5561ae192bc5b9167abced535d7" target="_blank" rel="noopener noreferrer nofollow"><span>IP Counsel, Copyright</span></a> @ Anthropic </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://www.linkedin.com/jobs/view/4433219542/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=af5cd02d67ae6a306a55ff6a6efaf8e639e36f19" target="_blank" rel="noopener noreferrer nofollow"><span>Embedded Legal Engineer</span></a> @ Palantir </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://jobs.cliffordchance.com/job/legal-technology-advisor-forward-deployed-in-london-jid-3004?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=a6acf7249072eb7eb4ceb14c1fd74b18ca277582" target="_blank" rel="noopener noreferrer nofollow"><span>Legal Tech Advisor</span></a> @ Clifford Chance </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://uk.indeed.com/viewjob?jk=8aeb46deb98413da&utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=2631145f3af5c2686925910bf1a704d567e26f01" target="_blank" rel="noopener noreferrer nofollow"><span>Legal Engineer</span></a> @ White & Case </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><a class="link" href="https://spellbook.com/careers?ashby_jid=e41772f0-d9d3-4bc5-9d40-cf92efdb076b&utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=6dc3b9602e761a8b3105ef22d5c642f075b8369e" target="_blank" rel="noopener noreferrer nofollow"><span>Legal Solutions Architect</span></a> @ Spellbook </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:#fc1919;font-family:Arial,Helvetica,sans-serif;font-size:0.8rem;font-weight:700;"><b>DATA</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h2 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><b>Law school didn’t teach you how to prompt</b></h2></td></tr><tr><td align="center" valign="top" style="padding-bottom:20px;padding-left:0px;padding-right:0px;padding-top:20px; " class="dd"><table role="none" border="0" cellspacing="0" cellpadding="0" style="margin:0 auto 0 auto;"><tr><td align="center" valign="top" style="width:636px;"><img src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80,width=1920,height=3840/uploads/asset/file/47e50ebe-1b3d-47e9-a0e2-b7de3fb43cd2/webinar-thumbnail-1__3___1_.jpg?t=1785770621" alt="" height="auto" width="636" style="display:block;width:100%;" border="0"/></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="background-color:rgb(255, 255, 255);">On August 11, former CLO Jamie Lieberman is leading a live class on how to write better prompts for contract work. </span><br><br><span style="background-color:rgb(255, 255, 255);">She’ll cover:</span></p></td></tr><tr><td style="padding-bottom:20px;padding-left:10px;padding-right:10px;padding-top:10px;" class="ee"><div style="margin-left:0px;" class="edm_outlooklist"><ul style="font-weight:400;list-style-type:disc;margin-bottom:12px !important;margin-top:12px !important;padding:0px 0px 0px 0px;"><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"><span style="background-color:rgb(255, 255, 255);">Her 5-part prompting framework</span></p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"><span style="background-color:rgb(255, 255, 255);">9 rules for better AI outputs</span></p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"><span style="background-color:rgb(255, 255, 255);">How to prompt for targeted redlines</span></p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"><span style="background-color:rgb(255, 255, 255);">How to avoid AI slop </span></p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"><span style="background-color:rgb(255, 255, 255);">And more!</span></p></li></ul></div></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> 📅 <span style="background-color:rgb(255, 255, 255);"><i>Tuesday, August 11, 2026</i></span></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> 🕐 <span style="background-color:rgb(255, 255, 255);"><i>12:30 p.m. ET</i></span></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="background-color:rgb(255, 255, 255);"><a class="link" href="https://spellbook.wistia.com/live/events/5bm13bl5ee?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=ea0c9369b7c68c2dc5096564f043d72f70b677a6" target="_blank" rel="noopener noreferrer nofollow"><span>Register Now (Limited Seats)</span></a></span></p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:#fc1919;font-family:Arial,Helvetica,sans-serif;font-size:0.8rem;font-weight:700;"><b>PODCAST</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h2 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><b>Why lawyers are working more but billing less, according to 10 years of data</b></h2></td></tr><tr><td align="center" valign="top" style="padding-bottom:20px;padding-left:0px;padding-right:0px;padding-top:20px; " class="dd"><table role="none" border="0" cellspacing="0" cellpadding="0" style="margin:0 auto 0 auto;"><tr><td align="center" valign="top" style="width:636px;"><img src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80,width=1920,height=3840/uploads/asset/file/791fdc2d-7c09-42ee-91cf-614f5ac9e61f/Newsletter_Thumbnail__5___1_.png?t=1785773039" alt="" height="auto" width="636" style="display:block;width:100%;" border="0"/></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> Joshua Lenon, Clio’s lawyer-in-residence, joins Mike to unpack what a decade of billing, payment, matter, and client survey data says about practicing law in 2026. </p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> He covers: </p></td></tr><tr><td style="padding-bottom:20px;padding-left:10px;padding-right:10px;padding-top:10px;" class="ee"><div style="margin-left:0px;" class="edm_outlooklist"><ul style="font-weight:400;list-style-type:disc;margin-bottom:12px !important;margin-top:12px !important;padding:0px 0px 0px 0px;"><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> Why flat-fee firms handle 8% more matters </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> Why fast replies win new clients </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> How payment plans lift firm revenue </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> What clients want that lawyers don't expect </p></li><li class="listItem ultext"><p style="mso-line-height-alt:150.0%;padding:0px;text-align:left;word-break:break-word;"> Why AI is growing the market, not shrinking it </p></li></ul></div></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> Full episode → <a class="link" href="https://open.spotify.com/show/1RqIrtqTgbng2BGuzr4aAq?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=ee6d1ae15041563878561b9852bf9b7f0815ab0f" target="_blank" rel="noopener noreferrer nofollow"><span>Spotify</span></a> | <a class="link" href="https://podcasts.apple.com/us/podcast/ai-in-practice/id1896630797?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=831244738a0f73a9bfba383964fb88adb71039c8" target="_blank" rel="noopener noreferrer nofollow"><span>Apple</span></a> | <a class="link" href="https://www.youtube.com/watch?v=a-4VyGvTpi0&t=1s&utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=3f909c590351d22913ef3df7ad5baddd4c4765ae" target="_blank" rel="noopener noreferrer nofollow"><span>YouTube</span></a></p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:#fc1919;font-family:Arial,Helvetica,sans-serif;font-size:0.8rem;font-weight:700;"><b>MEMES</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h2 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><b>The Entity</b></h2></td></tr><tr><td align="center" valign="top" style="padding-bottom:20px;padding-left:0px;padding-right:0px;padding-top:20px; " class="dd"><table role="none" border="0" cellspacing="0" cellpadding="0" style="margin:0 auto 0 auto;"><tr><td align="center" valign="top" style="width:636px;"><a href="https://x.com/lawyer_humor/status/2083295890224345267?s=20&utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=825135ebf912455a2b553cd91a9418a78f16a054" rel="noopener noreferrer nofollow" style="text-decoration:none;" target="_blank"><img src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80,width=1920,height=3840/uploads/asset/file/3ca73b93-b7d5-44f5-8b08-8d21bcf11139/SCR-20260804-hnau.png?t=1785844617" alt="" height="auto" width="636" style="display:block;width:100%;" border="0"/></a></td></tr></table></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" style=""><tr><td bgcolor="transparent" style="background-color:transparent;border-color:#C0C0C0;border-style:solid;border-width:0.75px;padding:12.0px 12.0px 12.0px 12.0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0"><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(252, 25, 25);font-size:13px;"><b>SUGGESTED EDITS</b></span></p></td></tr><tr><td class="dd" align="left" valign="top" style="color:#111111;font-weight:400;padding:0px 0px;text-align:left;"><h2 style="color:#111111;font-weight:400;mso-line-height-alt:150.0%;"><b>How’d we do?</b></h2></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><span style="color:rgb(0, 0, 0);">If you have suggestions for improving this newsletter, hit reply. We read every message!</span></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"><i>- Niko Pajkovic (</i><span style="color:rgb(0, 0, 0);"><i>Editor, The Redline)</i></span></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"> 📌<b> P.S. Get 50+ prompts for lawyers </b><b><a class="link" href="https://spellbook.com/ai-prompts-for-transactional-lawyers?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=4af71005b987272e8cd999b3b194a9308fd1f3f8" target="_blank" rel="noopener noreferrer nofollow"><span>here</span></a></b><b>.</b></p></td></tr></table></td></tr></table></td></tr><tr><td class="dd" align="left" style="padding:0px 0px;text-align:left;word-break:break-word;"><p style="mso-line-height-alt:150.0%;"></p></td></tr></table></td></tr></table></td></tr><tr><td align="center" valign="top"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td><tr><td class="b" align="center" valign="top" bgcolor="#000000" style="padding:0px 0px 0px 0px;border-style:solid;border-width: 0px 0px 0px 0px;border-color: #030712FF;border-bottom-left-radius:0px;border-bottom-right-radius:0px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td align="center" valign="top" bgcolor="#120307" style="padding:12px"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td><span style="padding-left:1px;"></span></td><td align="center" valign="middle" width="75" style="width:75px;"><a href="https://www.instagram.com/theredlineai/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=6e504c7d1ecfa1146c5ca663a3903226fef00cce" style="text-decoration:none;"><img width="22" height="22" alt="ig" border="0" style="display:block;max-width:22px;color:light" src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/static_assets/instagram_light.png"/></a></td><td align="center" valign="middle" width="75" style="width:75px;"><a href="https://www.linkedin.com/in/nikopajkovic/?utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=63bfc95885b52b9a46a93ede2068bc4b230294d3" style="text-decoration:none;"><img width="22" height="22" alt="in" border="0" style="display:block;max-width:22px;color:light" src="https://media.beehiiv.com/cdn-cgi/image/fit=scale-down,format=auto,onerror=redirect,quality=80/static_assets/linkedin_light.png"/></a></td><td><span style="padding-left:1px;"></span></td></tr></table></td></tr><tr><td height="10" style="line-height:1px;font-size:1px;height:10px;">   </td></tr><tr><td class="w" align="center" valign="top" style="padding:15px 15px 15px 15px;"><table role="none" width="100%" border="0" cellspacing="0" cellpadding="0" align="center"><tr><td align="center" valign="top"><p style="font-family:'Arial',Helvetica,sans-serif;color:#F8F8F8!important;"> Update your email preferences or unsubscribe <a class="link" href="https://the-redline.beehiiv.com/subscribe/SUBSCRIBER_ID/preferences?post_id=15573295-bca8-4ee8-ada7-1c2079745b03&last_resource_guid=Post%3A15573295-bca8-4ee8-ada7-1c2079745b03&utm_source=the-redline.beehiiv.com&utm_medium=newsletter&utm_campaign=crosby-seeks-liability-insurance-for-its-ai-agents&_bhlid=9f997e05f650561f84a65b14c938494e58e170a6" style="text-decoration:underline;text-decoration-color:#F8F8F8!important;color:#F8F8F8!important;"> here</a></p><p class="copyright" style="font-family:'Arial',Helvetica,sans-serif;color:#F8F8F8!important;"> © 2026 The Redline </p><p style="font-family:'Arial',Helvetica,sans-serif;color:#F8F8F8!important;"> 37 Front St. E<br>Toronto, ON M5E 1B3, Canada </p></td></tr><tr style="display: table-row !important;"><td align="center" valign="top" style="padding-top:20px;" style="display:table-cell !important;"><table role="none" border="0" cellspacing="0" cellpadding="0" align="center" style="display:table !important;"><tr style="display:table-row !important;"><td class="u" align="center" valign="middle" height="32" style="height:32px;display:table-cell !important; 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