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WithCoverage

AI-powered risk management for ambitious, scaling businesses

Distribution & Sales Growth Series B
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Overview

WithCoverage is a commercial insurance brokerage and risk management platform serving mid-market employers in P&C commercial and specialty/E&S lines. The platform combines AI-driven policy analysis with an in-house team of insurance specialists, attorneys, and claims professionals to audit existing coverage, identify gaps and savings opportunities, and negotiate with carriers on behalf of clients.

The technology layer includes proprietary AI tools for policy language analysis, carrier-to-carrier coverage comparison, industry benchmarking, contract review for insurance requirements, and automated data entry. Clients access a centralized portal for policy management, on-demand certificate of insurance (COI) generation, claims tracking, and coverage proposal comparison. WithCoverage operates on a flat-fee pricing model rather than carrier commissions, structuring its compensation around client outcomes rather than premium volume.

Founded in 2023 by JD Ross (co-founder of Opendoor) and Max Brenner (formerly of Bain and Compound), the company closed a USD 42M Series B in January 2026 led by Sequoia Capital and Khosla Ventures. Reported client results include premium savings of USD 80K to over USD 300K per account, with some clients achieving rate reductions of 30-57%.

Products & Services

Risk Management Team

Industry-specialized teams of insurance specialists, attorneys, and claims professionals organized by vertical. The team works alongside the AI platform to deliver advisory, carrier negotiation, and claims advocacy services across hospitality, construction, manufacturing, consumer brands, food and beverage, life sciences, apparel, and entertainment.

Key Features

  • Specialists organized by vertical for industry-specific expertise
  • Attorney support integrated into claims resolution
  • Carrier negotiation on behalf of clients
  • Proactive renewal oversight and policy management

Target Users: Fast-growing mid-market businesses seeking an alternative to commission-based brokers

AI Technology Platform

Proprietary AI tools that analyze policy language, compare coverage across carriers, benchmark against industry peers, review contracts for insurance requirements, and automate data entry workflows. The platform enables clients to identify over- or under-insured positions relative to comparable companies.

Key Features

  • Policy language analysis and coverage gap identification
  • Carrier-to-carrier coverage comparison
  • Industry benchmarking against peer companies
  • Contract review for insurance requirements
  • Automated data entry and policy digitization

Target Users: Operations, finance, and risk management teams at scaling businesses

Claims Management

Full-service claims handling that includes dispute resolution, attorney escalation, and proactive resolution workflows. WithCoverage manages insurer communications so clients are not responsible for navigating complex claims processes directly.

Key Features

  • End-to-end claims filing and tracking
  • Integrated legal support for disputes
  • Real-time status updates through the client portal
  • Proactive intervention on stalled or disputed claims

Target Users: Business owners and operations teams managing active or potential claims

Digital Client Portal

A centralized platform providing policy management and storage, on-demand COI generation, real-time claims tracking, digital applications, billing and payment processing, and a proposals dashboard for comparing coverage options.

Key Features

  • On-demand certificate of insurance (COI) generation
  • Policy storage and version tracking
  • Real-time claims status dashboard
  • Coverage proposals comparison view
  • Digital applications and billing management

Target Users: Finance, operations, legal, and executive teams across client organizations

At a Glance

Founded
2023
Headquarters
New York, NY
Employees
51-200
Funding
Series B

Category & Focus

Category
Distribution & Sales
Subcategories
Commercial Insurance Brokerage Risk Management Platform AI Policy Analysis
Insurance Verticals
P&C Commercial Specialty/E&S
Target Customers
Employers

Customers

  • Hungryroot
  • Chomps
  • GoPuff
  • Blank Street
  • Bluestone Lane
  • Tacombi
  • Caraway
  • Salt and Straw
  • Waterloo
  • GLOW
  • Bombas
  • Cuby
  • Modern Roofing
  • Romair Construction
  • Thirty Madison
  • Eight Sleep
  • Legendary Foods
  • The Escape Game
  • Kitsch
  • True Classic
  • Happy Dad
  • Farmer's Fridge
  • TMRW Life Sciences
  • Merrimak
  • Starke Contractors

Last updated: 2026-06-20