Oyster™

AI software for insurance agencies, brokerages, and wholesalers.

Distribution & Sales Startup USD 11.6M (Seed, Seed II)

Overview

Oyster Technologies is a New York-based AI software company for insurance, connecting agents, agencies, and carriers through an intelligent operating system. Founded in 2021 by Vic Yeh (CEO), Jon Patel (COO), and Nikhil Kansal (CTO) -- alumni of Blend Labs, Stripe, and Strategy& -- the company originally built a point-of-sale embedded insurance platform for e-commerce merchants and a usage-based rental insurance product for outdoor equipment rental shops.

In 2025, Oyster sold its insurance brokerage book of business to The McGowan Companies and pivoted exclusively to AI software. The team launched Cara, a domain-specific AI system for insurance agencies, brokerages, and wholesalers that automates the administrative workflows consuming agents daily time: coverage comparisons, proposal generation, certificate of insurance (COI) handling, ACORD form completion, and multi-channel client communications.

Cara raised an USD 8M seed round in April 2026, led by Kearny Jackson, with backing from notable angels including Claire Hughes Johnson (former Stripe COO), Kevin Mahaffey (SNR founder), and Sam Hodges (CEO of Vouch Insurance). The company reached seven-figure ARR within seven months of commercial launch, with over 80% of customers acquired through word-of-mouth.

Products & Services

Cara -- Agency Intelligence System

Cara is a domain-specific AI platform that functions as a 24/7 digital workforce for insurance agencies, brokerages, and wholesalers. It automates high-volume administrative tasks so agents can focus on premium production and client relationships.

Key Features

Copilot: AI command center for task automation and team workflow management
Servicing: Converts unstructured client communications (voice, email) into organized actionable tasks
Knowledge: Stores and retrieves agency documentation, internal knowledge, and account-specific data
Communication: Multi-channel client interaction via voice, email, and web
Quote research and coverage comparison
Certificate of insurance (COI) generation and management
Policy document analysis and exclusion review
ACORD and supplemental form completion
Errors and omissions review
Call triage and email assistance
Post-bind customer journey automation