Strategic Advisor, Insurance

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.
You're past wanting another full-time role. You're not done either. 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 Guide
Guide 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
• High-value use cases across QA, file review, reporting, leakage, and rework
• Stress-testing our product and rollout plans against what actually worked, and what didn't, when you launched something new
What we're building
• File and document first-read and orientation
• QA and risk review on open work
• Missing document and deadline detection
• Exception, leakage, and escalation indicators
• Summarization, chronology, and report generation
• Pre-submission review to reduce rework
• Guideline, SOP, and regulatory checks
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 claims.
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.

Work arrangement
Yes