Pie Insurance vs Kin Insurance
Side-by-side comparison of AI visibility scores, market position, and capabilities
Data-driven workers' comp for small businesses; raised $300M+; ML underwriting enables fast quotes through digital brokers; one of the largest insurtech workers' comp carriers in the US.
About
Pie Insurance is a Washington, D.C.-based insurtech company that provides workers' compensation insurance to small and medium-sized businesses through a technology-enabled platform. Pie uses alternative data sources and machine learning to underwrite workers' comp policies more accurately than traditional actuarial models, enabling it to offer competitive pricing to businesses in industries like construction, restaurants, and healthcare services. The platform delivers quotes in minutes through a digital flow that connects directly with insurance brokers and agents, who remain central to Pie's distribution strategy. Founded in 2017, Pie has raised over $300M from investors including Accel, Greycroft, and Moxley Holdings and has grown to become one of the largest insurtech workers' comp carriers in the United States. Pie's model captures the small business segment that is often underserved or overpriced by traditional carriers who rely on limited data for these accounts.
Chicago DTC homeowners insurtech (founded 2016); $50M Series E $2B valuation (Sep 2025) total $476M raised, $495M premiums (+43%), 160K policyholders in cat markets, IPO filing planned 2025 competing with Hippo for catastrophe insurance.
About
Kin Insurance is a Chicago, Illinois-based direct-to-consumer homeowners insurtech — having raised $476 million total including a $50 million Series E in September 2025 at a $2 billion pre-money valuation led by QED Investors and Activate Capital, plus $200 million in debt financing from Wellington Management — providing technology-driven homeowners insurance in catastrophe-exposed markets including Florida, Texas, California, Louisiana, Georgia, Alabama, Mississippi, South Carolina, Tennessee, Arizona, and Virginia where traditional insurers are retreating. Founded in 2016 by CEO Sean Harper, Lucas Ward, Sebastian Villarreal, and Stephen Wooten (entrepreneurs with fintech backgrounds from Groupon, Insight Venture Partners, and Avant), Kin operates as a Managing General Agent (MGA) writing policies on behalf of reciprocal exchanges it manages — a structure that gives Kin underwriting control and risk management authority while distributing policy risk through the reciprocal exchange mechanism rather than Kin's own balance sheet. In fiscal year 2024, Kin wrote $495.3 million in premiums (up 43% from $346.3 million in 2023), generated $156.1 million in total revenue (+48% YoY), served 160,000 policyholders (up from 115,000 in 2023), and the reciprocal exchanges it manages achieved their first full year of profitability with $12 million in operating income (+126%). The company's total insured property value surpassed $100 billion by April 2025, and Kin employs 800 people.
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