Why this might interest you You've spent a career in insurance. You know where the work breaks down and why, and you've watched AI arrive in this industry sold by people who have never done the job. Maybe you're still in a full-time role, maybe you're past wanting one. Either way, you're not done. You'd rather build something than take the occasional consulting call. You want to work for yourself, on your own schedule, with real ownership in what you help create. And you want the next thing you build to change how this industry works, not just keep it running. If that's you, we should talk. Structure Fully remote, 1x per week calls and async input Designed to fit around your existing work Equity and paid engagement compensation About GuideGuide AI is building an AI platform for insurance operations. Our belief is that half of the mistakes and paperwork in insurance can be resolved with the right AI support. We're building tools to help teams understand files faster, catch issues earlier, reduce rework, and close cleaner work, without replacing human judgment. What the role actually looks like Most weeks, it's a conversation. Product feedback, strategizing on sales calls, helping us break in-the-door, consulting on client engagements as the subject matter expert. Your expertise is valuable in: Networking with insurance leaders and operators Positioning and selling into insurance: pricing, procurement, buying committees, objections Where insurance teams lose time, money, and control Where AI can move loss ratios, retention and growth, not just cut handling costs Stress-testing our product and rollout plans against what actually worked, and what didn't, when you launched something new What we're building Claims: file first-read, missing-document and deadline detection, QA, leakage, and regulatory and guideline checks Summaries, chronologies and reports across the file Next: underwriting and distribution workflows (submission intake, coverage review, agency servicing)
About the team:
Our team brings experience from the Lloyd's of London insurance market, startup company-building, claims-adjacent operations, and AI product/infrastructure work. Across the team, we have built three AI products and are now applying that experience to insurance operations. Guide is backed by Sisu, a Silicon Valley startup incubator with LPs including operators and early builders behind companies like Skype, PayPal, and First Round Capital.
