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White Mountains Insurance Group

23 South Main Street, Suite 3B, Hanover, NH, 03755, United States

Overview

White Mountains Insurance Group, Ltd. (White Mountains or the Company) is a financial services holding company with primary business interests in property and casualty insurance and reinsurance. The Company's corporate headquarters and its registered office are located in Hamilton, Bermuda and its principal executive office is located in Hanover, New Hampshire.

Total investments
4
Lead investments
3
Investments · 12mo
1
Active investors
5

Sector focus

  • Banking
  • Financial Services
  • Insurance
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Investment portfolio

  • Bishop Street Underwriters

    Led · Equity · Feb 2026

    Bishop Street Underwriters operates as a managing general agent (MGA) platform focused on underwriting excellence, program launches, and accretive acquisitions. In 2025 the company surpassed $650 million in gross written premium while maintaining an industry-leading portfolio loss ratio below 50 percent, underscoring strong organic growth and disciplined risk management. Management plans to leverage its momentum to expand its global footprint in 2026, accelerating both de novo program launches and strategic acquisitions. The firm positions itself as a partner of choice for high-performing underwriters and operating partners across the insurance distribution landscape. Bishop Street emphasizes data-driven underwriting, scalable infrastructure, and a network of specialist MGAs to drive continued growth. The newly secured capital and strategic guidance are intended to fuel these initiatives and solidify the platform’s industry leadership.

  • Pie Insurance

    Participated · Series D · Sep 2022

    Pie Insurance provides digitally distributed workers’ compensation insurance to small businesses, selling directly via its website and through thousands of independent agents. The company uses data and analytics to price and underwrite policies and says it has maintained strong unit economics and sustainable loss ratios. In the first four months of 2022 Pie increased its annualized run rate premium to nearly $300 million and more than doubled its gross written premium in Q1 2022 versus Q1 2021. Since early 2021 through May 2022 the company more than doubled its number of policyholders and insurance agency partners. Pie has raised over $615 million in total capital since its 2017 inception. The company plans to use the new capital to expand into new lines of business and to transition to a full-stack carrier. Pie Insurance is a Washington, D.C.-based startup selling workers' compensation insurance to small businesses through an internet-driven, cloud-based platform. The company leverages proprietary data and analytics to provide faster, more affordable underwriting and sells directly online and through thousands of independent agents. Pie began selling policies in March 2018 and has grown its gross written premium to over $100 million while partnering with over 1,000 agencies nationwide. Revenues have climbed 150% since its $127M Series B extension last May, and headcount rose to 260 from 140 over the past year; the company declined to disclose recent hard revenue figures. Pie plans to use new capital to invest further in technology and automation, grow its core workers' comp business, and lay the groundwork for new business offerings in 2021 and beyond. The company was founded in 2017. Pie Insurance offers workers' compensation insurance directly to small businesses and via partnerships with local, regional, and national insurance agencies. The company operates as a managing general agency for Sirius America Insurance Company and provides A.M. Best A- rated workers' compensation coverage. Pie sells coverage in 34 states and the District of Columbia and is expanding nationwide. Founded in 2017 by CEO John Swigart, the firm is headquartered in Washington, DC and Denver, CO. The company plans to use new capital to grow its offering to small business owners and expand distribution through agents. Pie Insurance, founded in 2017, provides workers' compensation insurance directly to small businesses through an easy-to-use digital experience and operates as a managing general agency for Sirius America Insurance Company. The company began offering policies in 2018 and sold its first policy in March 2018. In the first 11 months since launch it generated more than $10 million in written premium and reports that 80% of small businesses overpay for workers' compensation coverage. Pie is available in 19 states covering more than 60% of the U.S. workers' compensation market and expects to expand nationally by the end of 2019. The company offers A.M. Best A rated workers' compensation insurance and plans to use new funding to expand geographically, add new distribution sources, and further simplify the customer experience. Pie Insurance offers near-instant online workers' compensation policies to small businesses through a frictionless direct distribution platform. The company built a full-stack managing general agent (MGA) operation and secured required regulatory approvals in under 12 months. It began offering policies in 2018 and today sells in eight states. Pie uses advanced analytics and a predictive model that estimates 80% of small businesses overpay for coverage—often by as much as 30%—to more accurately identify risk and simplify purchasing. Insurance offered by Pie holds an A.M. Best A rating. The company intends to use new capital to scale operations and expand geographically.

  • Buzzmove

    Led · Seed · Aug 2016

    Buzzmove, launched in 2014 and led by CEO Rebecca Downing, provides an online price comparison and booking platform for the moving industry that enables consumers to inventory belongings digitally and purchase home and household contents insurance. The company also offers SaaS-based professional surveying software to moving companies. Buzzmove participated in Startupbootcamp InsurTech prior to the investment. The startup is based in London, UK. The company aims to use raised capital to continue development of its platform. Buzzmove operates an algorithm-powered online marketplace that lets consumers inventory belongings, compare exact quotes from vetted movers and book removals online. Its front end uses proprietary inventory technology with a drag-and-drop interface and an algorithm at the centre to produce instant, exact quotes. The company launched a London beta in November and plans a nationwide U.K. launch and national marketing campaign to scale vendor participation and user bookings. Buzzmove has an exclusive partnership with the British Association of Removers (BAR) to vet and validate vendors listed on its site. Revenue streams include a 13% commission on removal bookings, referral fees for related services, and a monthly recurring SaaS fee. CEO Becky Downing says Buzzmove is first to market in Europe, with U.S. rival Unpakt as the closest competitor.

  • Vidado

    Led · Series C · Jan 2016

    Captricity provides a SaaS platform that transforms handwritten paper forms into digital data using crowd-guided deep learning. Its technology extracts data from paper documents, scans, faxes, emails, call centers and web forms, and connects automatically to backend systems to enable advanced analytics. The company serves insurance, healthcare, government and non-profit customers and lists New York Life, AXA, the FDA, the FEC, inVentiv Health, Xerox Healthcare and Innovations in Poverty Action among its users. Founded by CEO Kuang Chen and based in Oakland, California, Captricity commercialized its solution in 2011. The company raised $35M in a Series C and has raised $49M to date; it will use the new funds to expand operations. As part of the financing, Teresa Chia of White Mountains will join Captricity’s board. Captricity provides a cloud SaaS platform that converts static documents and handwriting into 99% accurate, machine-readable data using a combination of machine learning and human intelligence. It ingests forms via faxes, email attachments, scans or mobile phone photos and offers same-day turnaround for any volume. The company has processed data for clients across regulated sectors including health, government and enterprise, with customers such as the FDA, Symantec and Humana. Captricity has announced partnerships to scale its enterprise use cases, including a deal with New York Life Direct to digitize more than 500,000 paper-based leads annually and work with the FDA to digitize MedWatch reports for openFDA. The team emphasizes expansion in paper-intensive, compliance-driven markets like government, healthcare and insurance. Financially, the company has completed a $10M Series B and has now raised $14M in total. Captricity is a Berkeley, CA–based developer of a web app that turns handwritten documents into digital ones. It offers a self-serve data-entry service for digitizing paper forms and extracts data into digital tables via captricity.com and via an API for developers. The company’s solution has been used by Catapult Health, a team of economists from New York University’s Center for Technology and Economic Development (CTED), Code for America (Captricity participated in their accelerator program), the Fair Political Practices Commission of California, PrepSmart, the University of California, and independent insurance broker David Luc. Captricity raised $4.5M in venture funding according to an SEC filing. The filing lists Chamath Palihapitiya as an investor among 22 other backers. The company is led by founder and CEO Kuang Chen and Brian Busch, Director of Business Development. Captricity is a Berkeley, CA-based cloud service that captures digital data from paper documents. Founded in 2011 by Kuang Chen and Jeff J. Lin, the company converts scanned or photographed paper records into structured digital data. The Knight Foundation said it will help build awareness of Captricity’s products and services among its network of communities, nonprofits and media organizations. Financially, Captricity has raised $1.6M to date. Investors include Menlo Ventures, Charles River Ventures, Attractor Ventures, Sky Dayton, Greylock Partners, Social + Capital Partnership, Kapor Capital, Atlas Ventures, and the Knight Foundation Enterprise Fund. The company was actively hiring at the time of the report.

Team

  • Manning Rountree

    CEO

  • John J. Byrne

    Founder

  • Giles E. Harrison

    EVP and Chief Strategy Officer

    LinkedIn
  • Peter M. Carlson

    Director

    LinkedIn