Insurance Operations Specialist

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.