David Heales is a partner in the Corporate & Financial Services Department and a member of the firm’s Insurance Transactional and Regulatory Group. David focuses his practice on corporate and commercial transactions in the insurance industry and general insurance regulatory matters. He regularly acts in the acquisition and disposition of insurance entities, blocks of insurance business and insurance intermediaries. David also has extensive experience assisting insurtech companies, traditional carriers, inter-insurance/reciprocal exchanges and non-insurance entities in complex program management, managing general agent and distribution arrangements. David also advises clients on broad range of insurance regulatory matters, such as redomestications, licensing matters involving insurance companies and producers, holding company act filings, and investment law considerations.


  • Recognized in The Legal 500 US – Insurance: Non-Contentious (2022)
  • Named in The Legal 500 US – Insurance: Non-Contentious – as a “Rising Star” (2019, 2020, 2021)
  • Awarded a 2021 Pro Bono Publico Award from The Legal Aid Society

David has advised on the following significant matters*:

Insurance Mergers and Acquisitions

  • American Family Insurance Group in the sale of a majority stake in the attorney-in-fact of Trusted Resource Underwriters Exchange to funds managed by Gallatin Point Capital.
  • Advising iA Financial in its acquisition of Vericity, a publicly traded company servicing the middle-market life insurance space through Fidelity Life, an insurance carrier, and eFinancial, a direct-to-consumer digital agency, for $170 million.
  • Mitsui Sumitomo Insurance Co. Ltd. in its acquisition of Transverse Insurance Group.
  • Nestlé in its sale of Gerber Life Insurance Company to Western & Southern for $1.55 billion.
  • The Hartford in its acquisition of the Navigators Group for $2.1 billion.
  • The Hartford in its acquisition of the U.S. group life and disability business of Aetna for $1.45 billion.
  • A Bermuda-based insurance group in its $3.4 billion acquisition of a mortgage insurance business.
  • Numerous acquisitions and dispositions of insurance producers, third-party administrators and managing general agents, including:
    • Advising Bamboo Ide8 Insurance Services, LLC, in connection with an approximately $285 million equity investment from White Mountains Insurance Group, Ltd.
    • Acting for an life insurance carrier in its acquisition of a life insurance quoting and brokerage firm.
    • CNO in its acquisition of DirectPath, LLC.
    • CNO in its acquisition of Web Benefit Design Corporation
    • MetLife in its acquisition of PetFirst Healthcare, LLC.
    • Next Insurance in its acquisition of AP Intego.
    • Advising a major insurance group in its acquisition of medical stop-loss managing general underwriter.
    • A regional health insurer in its acquisition of a market-leading self-funded health plan third party administrator and technology platform.
    • A financial services holding company in its acquisition of a national commercial group insurance program manager.

Joint Ventures, Strategic Alliances and Innovative Insurance

  • Advising WillisTowersWatson on the launch of Verita, a managing general underwriter platform.
  • Stone Point Capital in its joint venture with AIG in forming an independent managing general agency serving High Net Worth and Ultra High Net Worth markets.
  • Ally Insurance in its issuing carrier relationship with Hippo, the homeowner insurtech, pursuant to which Ally has agreed to provide Hippo with up to $500 million of underwriting capacity.
  • General Motors in the launch of OnStar Insurance Services, an insurance platform leveraging the technology and telematics data of, its subsidiary, OnStar, including in the negotiating of the related co-development and distribution arrangements with Homesite Group.
  • Assicurazioni Generali in relation to a major joint venture partnership with Nationwide to promote, distribute and administer insurance solutions for multi-national property and casualty exposures on behalf of both organizations.
  • Advising various strategic investors and insurance carriers in the establishment of fronting insurance platforms, including through the formation and/or acquisition of various of portfolio carriers.
  • The Doctors Company in various commercial insurance distribution arrangements relating to its acquisition of the Hospital Insurance Company and its third-party administrator, FOJP Service Corporation.
  • Numerous insurtech entities, technology ventures and sharing economy companies, across all business lines, with respect to an extensive range of program management and product distribution matters, including:
    • Airbnb, an online travel booking marketplace in various commercial arrangements and insurance regulatory issues, including with respect to marketing and distribution issues.
    • Ladder, a digital life insurance provider, with respect to the negotiation of each of its key commercial carrier and reinsurer partnerships.
    • Policygenius, the leading online insurance marketplace, with respect to a wide range of insurance regulatory and insurance distribution and marketing matters.
    •, a cyber-analytics firm, in the launch of its cybersecurity program manager, Resilience, and including the negotiation of its program management arrangements with Intact Insurance Specialty Solutions.
    • Next Insurance, a small business insurance provider, in various commercial arrangements, including with respect to marketing and distribution issues.
    • Better Mortgage, an online mortgage originator, with respect to various insurance regulatory and commercial issues.
    • High Definition Vehicle Insurance, a next-generation commercial auto insurance business, in each of its key commercial agreements and in the development of its template distribution agreements.
    • Bestow, a digital life insurance provider and insurance services company, in various insurance regulatory and commercial issues, including with respect to a major insurance distribution and technology partnership.
    • Spot, a digital accident and health insurance agency, in numerous commercial and insurance regulatory matters.
    • Embark Veterinary, a dog genetics company, in its pet insurance distribution and co-development arrangements with Pumpkin.
    • Signal, a life and annuities IMO platform, in various commercial arrangements and insurance regulatory issues, including with respect to marketing and distribution issues.
  • Advising an asset management firm on the formation and launch of a managing general agent with a focus on underwriting risks from the blockchain and digital asset sectors.

Insurance Regulatory

  • Insurance carriers, intermediaries and reinsurers on regulatory compliance, governance, licensing, financial and market conduct examination, Insurance Holding Company Act, privacy and data securities laws and current and prospective digital distribution matters.

* David advised on some of these matters prior to joining Willkie.



Oxford University, M.A.

Bar Admissions

New York England & Wales

Events & Speaking Engagements

Speaking Engagement
Corporate Liabilities Deals