Why Kay.ai
We’re building AI co-workers that eliminate repetitive data entry in insurance operations. Right now, we’re riding the wave of rapid growth and scaling our team fast. Here’s why you should join us:
Pushing frontier tech every day: We’re solving some of the hardest challenges in LLM reliability, browser automation, and adaptive workflows.
Right Market Opportunity: The need for automation has never been more urgent in insurance (40% workforce bogged down in admin tasks, 400K worker shortage expected by 2026).
Demand Outpacing Supply: 100% MoM growth, strong word-of-mouth, saving >100 hours/month for clients, and the right market positioning mean we’re growing faster than we can handle.
World-class team and advisors: Our team includes machine learning experts and insurance operators from Microsoft, Amazon, Twitter, AmWINS, Insureon, and IITs. We’ve also assembled a top-tier panel of insurtech founders and insurance executives as advisors.
Strategic investors: We’ve raised our seed round from investors with deep expertise in AI and insurance, including Wing VC, South Park Commons, and 101 Weston Labs.
What You’ll Build
As a HITL (Human-in-the-Loop) Specialist, you’ll act as both executor and expert across our insurance workflows. You’ll be the human eyes and hands helping our AI co-workers learn faster and perform better. Specifically, you will:
Complete and review insurance operational workflows using our internal platform.
Identify failure points, missing logic, and system bugs as a true end-user.
Collaborate directly with product and engineering to test prototypes, validate changes, and ship features that reduce friction in our quoting engine.
Support the On-Call Specialist team by assisting with onboarding, live workflow coverage
Help develop scalable SOPs and internal documentation to improve task accuracy
Surface high-impact improvement ideas based on real submission behavior, client needs, and workflow insights.
About You
You have 2-5 years of experience in commercial or personal insurance operations, preferably with exposure to quoting, processing, or rating.
You love to spot process inefficiencies and are naturally detail-obsessed.
You’re excited by technology and can quickly adapt to new tools and systems.
You’ve worked in fast-paced environments where documentation is evolving and priorities shift quickly.
You’re confident communicating across teams and giving structured feedback.
You’ve either trained, mentored, or led others - or are eager to grow into that role.
Bonus: Experience at an insurtech, MGA, agency, or startup is a plus.
Compensation, Benefits, and Perks
Competitive salary and generous equity
100% coverage health, vision, and dental insurance; 20% coverage for dependents
Beautiful NYC office space right off Domino Park in Williamsburg
If This Isn’t the Right Role for You
Please take a moment to reflect on the 1 or 2 most brilliant collaborators you’ve ever worked with and consider whether this might be a fit for them.
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