Counsel, AI Liability & Claims at Ollive AI

As Counsel for AI Liability & Claims at Ollive AI, you will define how emerging AI risks are priced, evidenced, and adjudicated. Reporting to the Head of Underwriting, you’ll bridge the gap between complex legal theory and technical telemetry, shaping both a novel insurance product and the platform that detects liability in real-time.

• Assess liability exposure from AI pilot findings, estimating defense costs and regulatory outcomes for negligence or misrepresentation.
• Define technical evidence requirements for engineering teams to ensure agent logs can effectively establish or rule out liability.
• Build the claims function from scratch, including handling procedures, reserving guidelines, and establishing a US/UK panel of defense firms.

• 5-10 years of experience defending liability claims in technology E&O, cyber, or professional liability at an insurer or MGA.
• Qualified to practice law in at least one US state or as a solicitor/barrister in England and Wales.
• A hands-on builder mindset with a deep habit of establishing the root cause of losses through technical records.

• Shape a brand-new insurance category for the AI agent economy before claims history even exists.
• Work at the intersection of law and engineering, translating agent logs and telemetry into actionable legal evidence.
• Join a specialized, high-impact team building a runtime risk layer that blocks or redacts harmful AI outputs in real-time.